“I want to look back on my career and be proud of the work and be proud that I tried everything.”
If you’re in your mid-thirties to mid-forties this post is for you.
I’ve trained thousands of candidates for the CFA exams and hundreds of them have got the prized CFA charter. More importantly, I am in touch with the majority of this last group of CFA charter holders, many of whom are in the 35–45 age group. Hence, I have a ringside view of what happens in the minds of many of them.
I am also connected via WhatsApp and LinkedIn to many (including ex-colleagues) in that age group.
This is what I have noticed.
By the time they hit 35 years of age, many of them have been at least moderately successful as defined by the below:
• They are well educated, i.e., have a post graduate degree or a professional qualification.
• They’ve probably spent at least 10 years in corporate life.
• They’ve got 3–4 promotions.
• They earn a decent amount by which I mean enough to maintain their family in comfort.
• They are a respected member of their profession and hence of the related networks.
• They have managed small-to-medium-sized teams.
• Their juniors respect their experience and come to them for advice.
• They are competent at technical stuff.
But, the other side of the coin is that:
• They’ve changed quite a few jobs so far but it’s similar shit in a differently packaged and pricier bottle.
• Work has become routine and boring, and they’ve stopped learning.
• They feel unappreciated at work.
• The politics at work has increased as they climbed the proverbial ladder and has occupied some of the space that formerly belonged to actual work. They’ve to now deal with not just the job but also jerks, not only the performance but also the politics.
• Their “network” is the same uber narrow group — people with similar age, education, industry, and nationality.
• They toy with the idea of entrepreneurship, but they’ve no idea what or how.
• They start thinking that there must be more to life than this.
Welcome to the midlife career crisis, a term coined by the Canadian psychoanalyst and organizational consultant Elliott Jaques. It’s that period in our lives when we come face-to-face with our limitations, our restricted possibilities, and our mortality.
The crisis is also part of the Happiness U-curve.
A group of economists working with Professor Andrew Oswald of The University of Warwick found that the job satisfaction of the average employee falls dramatically in midlife. On average, life satisfaction is high when people are young, then begins to decline in the early thirties, bottoming out between the mid-forties and mid-fifties before rising again to levels as high as when it was during young adulthood.
Why does this happen? We can understand this by dividing life into three phases.
• Young people wear heavily rose-tinted glasses.
• They expect big jumps in life satisfaction.
• Most of them think that they’ll not be like the average person and will end up with a great job, a happy marriage, and smart and healthy children.
• The problem is that’s not how things usually work out. Our hopes and plans meet reality.
• The climb up the career ladder may not be as quick or smooth as we expect. Or maybe we climb fast and get to the top, but we don’t like what we find there — long hours, stress, politics, lack of learning, lack of meaning/purpose, stagnation, and so on.
• This is also the time when we sharply revise our expectations downwards. So, it’s a double whammy — disappointments and ditched aspirations.
• At the bottom of this U-curve (around the mid-fifties) expected life satisfaction finally aligns with current life satisfaction.
• People reluctantly throw away the misleading tinted eyewear and wear plain glasses, finally accepting that this is their life.
• By this time, all the memories of all the past screw-ups (flunked exams, wrong career moves, poor lifestyle choices, destroyed relationships, failed marriages, disastrous investments, etc.) start fading and you feel less regret.
• This mix of acceptance and less regret about the past boosts life’s satisfaction.
Why do things improve after the crisis?
• People realize what’s really important to them. They start investing in strong relationships and they get a lot of happiness from these.
• Midlife is a time of recalibration, when they begin to evaluate their lives less in terms of social competition and more in terms of social connectedness.
• You start accepting your limitations.
• Social reasoning and long-term decision-making improve with age, spirituality increases, and older adults feel more comfortable coping with uncertainty and ambiguity.
In short, youth is a period of perpetual disappointment, and older adulthood is a period of pleasant surprise.
“The truth is that our finest moments are most likely to occur when we are feeling deeply uncomfortable, unhappy, or unfulfilled. For it is only in such moments, propelled by our discomfort, that we are likely to step out of our ruts and start searching for different ways or truer answers.”
Advice to anyone younger than 35 years:
1. You must be on the right track before you’re forty years old. Don’t fast-track yourself to middle management where most people get stuck.
2. Go out and get responsibility. Get management experience. Replicate what senior people are doing at a more junior level.
3. The field of finance is often terrible at teaching people to be good people managers because of the inordinate focus on the numbers and the process. You’ve to acquire those soft skills early, ideally by working with some good bosses and/or mentors.
Advice to anyone close to or going through the midlife crisis:
1. The first thing to grasp is that nothing is wrong with you, and you aren’t alone. The story of the U-curve is a story not of chaos or disruption but of a difficult yet natural transition to a new life.
2. It’s not just good but important to acknowledge mid-career dissatisfaction as a normal and temporary stage in your work life. This provides a sort of light at the end of the tunnel when you feel like there’s no hope.
3. If you have been hit by this not so uncommon mid-career illness you can learn from those older than you (relatives, friends, colleagues, mentors, coaches) who’ve already been through this tough phase and have emerged feeling less regret, having adapted to life’s circumstances. Don’t reinvent the wheel.
4. Yes, a mid-career crisis can be a hellish time. But, it can also be a chance to introspect and reevaluate your values, behaviors, preferences, strengths, and weaknesses. It’s quite exciting when seen from that perspective. It’s like a second chance.
5. You can choose to wait out this storm of discontent and frustration or make some big changes in the hope of a happier future. Whatever you do, this phase shall pass because things can only get better.
6. Perhaps it’s time you stopped looking at work or money or reputation as the biggest source of achievement. Perhaps you can now measure your worth by how you help others and contribute to the community or how well you are growing as a person, both mentally (e.g., self-awareness and calmness) and physically (eat healthier, train hard, and gain a shredded body).
7. Start enjoying the relationships that you’ve (hopefully) been developing over many years — friends, ex-colleagues, mentors, mentees, and so on.
8. Feel grateful. There are always things that are relatively quite good in your life that you never paid attention to because you were always comparing your expectations and comparing yourself with others. Gratitude is helpful because when you feel like shit due to all the errors and omissions in your life you can pull out the Book of Blessings and feel grateful. That “attitude of gratitude” (such a cheesy phrase but so accurate) will jack up your sense of satisfaction.
My first major change happened in the well-publicized and well-known age for transitions — 40 years.
This is when I chucked my jacket and tie and said goodbye to my corporate career.
This tale of transformation starts at the beginning of the year (perfect timing — a fresh start!). After spending a few months in a hellhole role, I’d landed a well-paid job in a senior role at a high-profile company. Notice that the last sentence ticks off almost all the boxes that indicate career success — “well paid,” “senior role,” and “high-profile company.” My boss was all milk and honey during the interview, a veritable Huggy bear, and I thought that was it.
Except it wasn’t.
My boss turned out to be a mix of Machiavelli and Kim Jong Un (Middle East version), which meant he was a micromanaging paranoid freak who only got to where he was by assiduously practicing the sophisticated art of kissing ass. He would walk into conversations I was having with colleagues and half seriously ask us, “if you are plotting to take my job.” He would (I found later after I’d quit) complain to his boss about me without once ever giving me direct feedback on my performance. He would spend 2 hours critiquing an email I’d drafted, including comments on how bad my written English was. He would suddenly and inexplicably emit veiled threats and warnings (“I know about you”) in the midst of one-to-one conversations.
It also appeared to be a corrupt workplace and there were strong suspicions that top management was ripping off the investors and filling up their own pockets. The markets had collapsed after a liquidity and greed-fueled boom, and they didn’t look like recovering soon. All this ensured the investors wouldn’t get the expected returns, and the company’s reputation and solvency were at risk.
Anyway, I was at my wits end and soon I quit.
That decision was one that will be etched in my memory forever. It was in the evening after an acrimonious discussion with my boss. The office lights were off, except in my office. Everyone had left. I was sitting on a higher floor in my office building, gazing at the lights of the traffic below. I tried tallying all the pros and cons.
1. The money was good.
2. The title sounded senior enough and powerful to anyone.
3. I looked after the finances of highly visible multi-million-dollar projects stretching across many countries.
4. The job looked like a safe haven smack in the middle of the biggest financial crisis in eight decades.
1. I had little or no operating freedom thanks to the system and my micromanaging superior. It was essentially a glorified coordinating and monitoring role.
2. Because of #1 above. I was learning next to nothing.
3. It was a highly politicized environment where you got ahead by being loyal to the Big Boss (as solemnly intoned once to me by my boss).
4. There were suspicions of corruption, and it was apparently at the highest levels.
5. There was a lot of stress, mostly triggered by my boss.
6. I hated the city where my office was sited — it was new, tiny, and I knew no one outside the office.
7. Since I, like many other people, have an inherent dislike for stress, politics, corruption, and micromanagement, I was clearly there for the money and the title.
8. But, I didn’t need the money as I was single, led a spartan lifestyle, had no family to maintain, no kids to send to college, and no onerous financial liabilities.
9. The title was meaningless in the overall scheme of things.
10. I was about to turn 40 and all the above made me realize that this was no way to spend my life.
That’s when my fellow co-founder and I had a long chat over the phone. The CFA prep company I had co-founded had been running for 9 months by then and the future looked very promising.
To quote my co-founder:
“You love teaching, and you are very good at it. Why don’t you chuck this job, fly back, and take over as the CEO? The company has been running with just one admin guy and needs leadership anyway.”
That declaration was like the key that unlocked my handcuffs. I literally felt like that. Unshackled. Suddenly, I felt not just a free man but the fear and uncertainty as to what I would do next disappeared.
I slept over it, and the next day handed my access card and official Blackberry (Yes dear reader I am that old) to the HR Director, a nice guy who urged me to think this over the upcoming weekend and reconsider, since I was the only strategic hire the company had made in a long time.
“In a chronically leaking boat, energy devoted to changing vessels is more productive than energy devoted to patching leaks.”
I dutifully thought this over during the weekend more to humor him (and look mature) than anything else. On Sunday morning I went back and told him my mind was made up.
That was the end of my corporate career. Today, I look back and think that was the second-best decision I made (the best decision was staying single) and hence have zero regrets.
1. Quitting isn’t for everyone
Let me start by saying that I am not even suggesting that you, dear reader, should walk up to your jerk of a boss to say “f**k off” and email him a stinker copying the entire company (although that would be epic!). This is not a call to arms. Situations are different and I completely understand.
2. Context is critical
My situation was special.
I was (and still happily am) single without the big worry of household expenses, travel, entertainment, rent, medical expenses, college education, and so on that comes with being married and having children. If you can manage a cheap and easy divorce and give custody of the kids to the spouse, go for it.
Just kidding. Or am I?
3. Options
But, if you can’t quit (the vast majority of the human race) then these are your options:
• Grin and bear it while looking for a job with similar pay and title.
• Talk to a coach about what next.
• Become the E word that is so sexy these days — an entrepreneur.
Luckily for you I have covered coaching earlier in this book and I will cover entrepreneurship in the next few sections.
You can thank me later.
This second and latest transition was after the company that I co-founded and led was acquired by a US entity, a training and publishing giant with a global footprint. I stayed on as the managing director.
I was soon reporting to a UK-based team, all ex-trainers, which meant they understood the business well. They were bright and highly experienced but more than that they were unfailingly polite, patient, adopted a hands-off approach, and stepped in with their considerably large and varied resources when we asked for support.
Ideal, yeah? Not really.
Because authenticity and freedom are two of my values. Probably my top two values.
Hence within 6 months of the acquisition I was feeling the old bug again, a certain lack of liberty and absence of learning (see a pattern here?). After building a respected brand from scratch, I felt my abilities were mostly wasted at the new setup. I felt I was drifting, lacking the independence, purpose, and passion that had driven me for the last 8+ years. I wasn’t making any impact so why continue was the constant thinking.
I was listless at work and couldn’t bring myself to launch any new initiatives. I distinctly recall being worried about my impact and legacy. Deprived of a purpose, the fear of mortality that I had always pushed to the back of my mind for the past few years came forth.
Overall, not a nice place to be.
Which sounds like an ungrateful thing to say as I was, from an external perspective, probably in the best place I’d ever been in my life. Just think:
• The company I co-founded and led had been acquired by a globally respected brand which is known to be quite picky about acquisitions.
• I was financially independent and could retire immediately if I wanted to.
• I was well liked by my team, more so than at any other point in my career.
• I was respected and admired in the training and CFA community in the GCC and even in India.
• I had two highly respected qualifications — I was a Chartered Accountant and a CFA charter holder.
• I was healthy and fit, much more than most people of my age and even more than many youngsters.
• I had a large following on LinkedIn of people who regularly messaged me for advice on higher education and career.
• I had no obligations to anyone — emotional or financial.
• I had no wife and kids to restrict or frustrate me.
Strange.
Then at the end of the year as was my custom I flew down to my hometown to where my mother lived. Two things happened that I will never forget and that changed my outlook.
While I was in my hometown, I was reading The Subtle Art of not Giving a F**k by Mark Manson and that was a transformative experience. Mark’s central point was that we give too many fucks about too many things when we shouldn’t. This causes anxiety and distress. His advice was to know your values, stick to a few nonnegotiables and leave everything else. This is a book you must read.
Was my mother. More precisely the way she lived.
She was 83 years when I came by for the flying visit and she was super active. She’d wake up early, meditate, direct the maid, cook a simple meal, work on her next book, read, talk to a zillion people on the mobile phone, and so on all without the slightest hint of indifference, frustration, or anxiety.
That hit me hard.
I told myself if an octogenarian living alone can carry on like this I should do better, much better. It struck me that I was being a wimp. With so many blessings to count, I was also being ungrateful.
After I flew back to Dubai, I decided that this was not my place. Within 2 months I resigned from my position as managing director.
My third act (after corporate and entrepreneurship) kicked off when I set myself up as an executive coach.
I had obtained the Level 7 Certificate in Coaching and Mentoring from the UK-based Institute of Learning and Management (ILM) back in 2018. This is a rigorous and respected qualification that took me the better part of 3 years to complete, and I learnt a lot about myself and executive coaching.
I did this because during my long training career I lost count of the number of times students told me I was pretty good not just at teaching but also mentoring. Plus, I am an endurance athlete (mountaineering and cycling) and that made me super curious about high performance. I was keen to study a comprehensive framework that explained the concepts, tools, and techniques leading to exceptional performance.
These days my clients are senior executives (MDs, Heads, CEOs, COOs) who want to be better leaders or who are stuck in their careers and are looking for solutions.
1. Step back
Whenever you feel stagnant you need to be open to looking at your life from another angle. Because most of us are in the thick of things 24/7 with little chance to get a fresh perspective.
This new look at life can come from anywhere. Mark Mansion and my 83-year-old mother gave me the metaphorical kick in the ass that I needed.
2. Live your values
I know it may sound obvious but when you feel disengaged it’s a big red flag that you are not doing what matters to you. You are living a life not meant for you.
In my case authenticity, freedom, and meaningful work were values that meant a lot to me and the discomfort I was experiencing told me I was in the wrong place. I had to leave what I was doing and head in the right direction.
3. Practice gratitude
We have two big issues that plague our abundant society — we take so much for granted and we are never satisfied even if we achieve great things, things that we craved not so long ago.
Many of us have jobs that often pay us more than we spend, three good meals a day, a good house, a quality vehicle, and all the conveniences of contemporary life ranging from Netflix to Uber to Zomato at our fingertips. Yet….
Count your blessings daily. You will be surprised how much you have. It’s often an effective antidote to the corrosive poison of ingratitude.
When you reach a certain level in your career you can stagnate — the work gets easy and boring, and you hit the glass ceiling as there are far fewer opportunities. That’s when you must explore solutions.
Uncovering your transferable skills is a solution.
I am an aviation fan, so the below example is not only apt, but it was also quite interesting to research and write about as well.
When Covid struck in early 2020, one of the first sectors to be decimated was travel. Air travel ground to a halt and airlines had to fire thousands of pilots, cabin crew, and also ground staff. That went on for many months because even after travel resumed, recovery was slow and unsure, and airlines became shrunken versions of their former selves. I had a ringside view living in the UAE because two of the world’s largest international carriers (Emirates and Etihad) are based in the UAE.
Amidst all this devastation caused to livelihoods, I recall seeing several articles on transferable skills of airline crew.
Take an airline pilot.
If you think of a pilot, you’d think all the chap needs to do is take off and land the aircraft, wear impressive looking uniforms, and flirt with the attractive cabin crew. After all, most modern airliners are super safe, fitted out with many gadgets and with multiple redundancies and these machines are mostly flown electronically and by autopilot.
But, I dug a bit more and found that an airline pilot must have a shipload of skills, many of which are transferable to (and applicable in) a nonflying career.
How much of the above is transferable? A lot.
Because these are all skills that a pilot can potentially use in a nonflying career, including a desk job at an airline (probably one reason why many airline CEOs were pilots once) or in a completely different industry.
Some people have difficulty in transitioning because they believe they don’t possess any significant transferable skills. They often lose hope and get depressed and anxious.
Think of what you can offer and where.
1. Search wider
If you can’t find a job in your field in such a situation you must look wider, beyond your academics and current and past roles and assess your skills.
For example, someone who has gone through the journey as an equity analyst most likely has excellent skills in (a) analysis, (b) research, and (c) written communications. A good teacher is a domain expert and also good at grasping and simplifying complex concepts and communicating these. These are skills that are transferable and valuable across many domains.
Don’t label yourself narrowly and hence lose out on opportunities. Talk to a recruiter and you may get a better idea of your skills and (equally importantly) what the market wants.
2. Know your technical skills
Surely after many years of slaving away from 9.00 to 5.00 (or longer) and after having risen through the ranks you must have picked up skills that can be used across industries? Because you were busy as a beaver, you never realized that:
a) you’d acquired some pretty useful technical skills and
b) these had lot of value outside your industry or company.
You and your colleagues simply took these for granted. This is part of what I call the big “blind side” of many executives.
3. Take stock of your soft skills
You may have noticed that all the transferable skills of an airline pilot listed above are soft skills. That’s probably why these skills are taken for granted — they are mostly intangible and not tangible technical stuff that you can pick up from a specific course or qualification.
Paradoxically it’s also soft skills that are the most valuable and transferable. Start working on these now. They may be immensely useful not just where you are but where you may be heading.
For both technical and soft skills, take pen and paper and make an inventory of your top ten skills. One way to arrive at this is to think of what your clients, colleagues, vendors, superiors, investors, and so on have consistently praised you for.
4. How to sell yourself
There is the big issue of convincing potential employers that although you have no experience in that industry, you have relevant skills from another, unrelated industry. There may also be the issue of overqualification. How do you tackle these?
This is when your selling skills become critical. You can:
• propose that (compared to what you were getting) you are Ok with an initial lower pay and/or a relatively junior position.
• suggest that the pay and role be upgraded after say, 6 months when you’ve proved yourself on the job.
• keep track of and show them proof of work that you’ve done in the past that is relevant at the new company. It could be an instructional video, a written report, a PowerPoint presentation, a financial model, and so on, as long as you don’t violate confidentiality or other legal requirements.
• get references from your former employers that specifically refer to some or all of the transferable skills that are essential at the new job.
• keep track of and show the potential employer emails sent by your former colleagues, clients, vendors, former bosses, and others that specifically talk about your accomplishments where the transferable skills were used. For example, a congratulatory email on achieving a tough sales target or with a difficult client or in a difficult market.
5. Qualifications
In addition to transferable skills, it often helps a lot if you also have a qualification that is relevant in the industry you plan to move into.
The CFA or master’s in finance comes to mind for anyone wanting to switch to a career in investing. In some cases, the qualification may be acceptable in lieu of relevant experience. Check what employers prize in your industry and location. Not all certifications or qualifications are equally well regarded everywhere.
Quite a few who I know and who are not already in core finance want to get into core finance, that is, asset management, equity research, and investment banking.
Which brings me to a question that I have been asked many times that runs broadly on the below lines:
“I don’t work in finance, but I want to work in investing. How do I do that?”
Hmmm.
This is a complex topic that demands a nuanced and detailed response in the form of the coaching tips below.
But, first I need to set the expectations right. Let me give you ten examples of successful transitions that I have seen in my 15 years of training and mentoring (both CFA candidates and CFA charter holders) and by interviewing guests on my Real Finance Mentor podcast.
Just to be clear, by transition I mean a significant change of career, not just a promotion or a change of title or a move that is normal for people with a specific combination of education, experience, and skill sets. So, Yours Truly doesn’t consider the below common moves as transitions although it may involve a change of industry, employer, and title:
• Investment Banker to CFO
• CFO to CEO (in the same industry or company)
• Equity analyst to Bond Analyst
• Relationship Manager to Investment Advisor
• Wealth Manager to Private Banker
Right, on to the ten examples of transitions.
I like to come to a conclusion based on data and now that we have the grand sample size of ten (!) let’s see what the conclusions are:
1. Transitions are extremely rare
I’ve taught probably 4,000 + students as part of my decade-long life as a CFA prep trainer. I have also interacted with hundreds of others as part of my longish career.
Since my memory is decent, the fact that I can only recall ten names tells you a lot about how uncommon career transitions are.
Not impossible, just uncommon.
That shouldn’t discourage you. I suspect the main reason for this rarity is not the lack of opportunity but the unwillingness of many to switch careers even if they have the ability (the potential and no constraints — fiscal, familial, or otherwise). They are in their comfort zone.
2. Qualifications are important
In some situations, a qualification helps hugely in making a transition.
You’ll see that many in the above list had the CFA charter (or were very close to getting that) when they made the jump.
This is logical. When you walk into an interview room with zero experience you must have a near substitute for the employer to look at. A globally respected qualification (like the CFA charter) is hence invaluable as a substitute. It shows that the candidate is serious about a career in a specific field and that he has undergone rigorous testing to be a professional in that field.
Your keen eye will note that most of the ten were around 30 years of age when they made the jump. Again, quite reasonable for many reasons:
• When you are younger it’s easier for your new employer to mold you. As you age it’s perceived that you become inflexible and less open. Call it ageist but that’s the way it is.
• If you rack up too many years in a field (e.g., accounting or audit or risk management) you risk being branded as an auditor or accountant or risk manager. This is great if you want to continue in the same line because the track record matters. This is terrible if you want to switch careers because the track record matters.
• What is “too many years”? Depends, but anything over 5 years can be a turn off for most potential employers.
• The more time you spend in a career, the higher the inertia thanks to the powerful combo of higher compensation, bigger title and of course the comfort of the steady paycheck. It’s quite tough to summon up the motivation to start another career with all the attendant uncertainties. Most of the time the inertia overcomes the motivation.
4. But …
It’s definitely not game over if you are older for two reasons:
• You can transition to a leadership role when you’ve many years of management experience although you may be in your forties or fifties. Why? Because when hiring for a Head, GM, COO, CFO, or CEO position companies are more likely to value more of your soft skills and reputation and place far less emphasis on the technical expertise gained in a specific domain. I suspect that was the case for #8 in my above list.
• You stand a better chance of succeeding as an entrepreneur if you decide to start after 40 years.
• A 2018 research paper published in the Harvard Business Review found that the average age at which a successful founder started their company is 45 years. That’s “among the top 0.1% of startups based on growth in their first five years,” according to the report. Because by then you’d have spent about 15–20 years in corporate life and you know yourself and your field quite well, have built a good network and may even be a good people manager.
5. Know thyself
Know yourself and do that as early as possible.
It doesn’t and shouldn’t take 5 long years for you to grasp that accounting or audit or operations doesn’t float your boat. The first year or full cycle should do it. Kick back your heels and think unemotionally as to where you are and where you want to be.
Also think widely about your options; a lot of the time we are simply unaware of what else we could do because no one told us. We are like the proverbial frog in the well, so busy and thinking that the well is the whole world.
6. Target the right employer
If you want to make a career transition, the chances are better if you target a smaller entity in your target field.
That’s because the small fry is less picky compared to the big fish and you could at least get an interview call with them. Whereas your resume is highly likely to be rejected outright by the HR Team at Big Company Inc (or worse, by an unfeeling AI-driven screening software).
Which means that if (for example) you are a Senior Manager in credit or market risk at a bank and want to enter Fintech stop looking at Square, PayPal, Visa, Mastercard, and so on and search for a relatively new and less known boutique firm.
7. Connections matter
Yes, I know I’ve been beating the drum about networking in this book.
But, who you know matters a lot when on paper you are unfit for the role as is the case when switching careers. This is why I tell people to nurture relationships with colleagues, bosses, professors, and so forth from a young age.
Binod’s Third Rule of Networking says, “If thou art an introvert thou shalt kiss thy chances of a successful transition goodbye.”
The earlier point was about changing within corporate.
The move from corporate to entrepreneurship is at a different level altogether. That’s a bigger jump.
It’s so easy to say, “I am sick and tired of this shit job with a jerk boss and horrible clients, and I am going to quit and start my own business.”
But, making it happen is another thing altogether.
I have talked to many currently in middle and senior positions in finance and I discovered that there are several hurdles standing in the way of the typical corporate warrior who dreams of becoming an entrepreneur (I will talk of some practical solutions in the Coaching Tips section later).
Let me list out the top ten challenges:
1. No idea
You lack a feasible business idea. This is of course fundamental.
2. Fear of failure
You have a business idea but are shit scared that it may bomb, burning not only precious capital but also the career that you’ve so carefully built up over the last many years.
3. Good but not great
You do have a business idea, but you doubt whether it’s streets ahead of the next best substitute or the competition. It’s probably a mere 20% better in a world where the market demands that a product or service be 100% better to stand out and scale.
4. Tech simpleton
You do have an idea but there is a big technology component in your business, and you may be many things, but you aren’t a techie.
5. Salary seduction
The lure of a stable salary from the current job is just too powerful, especially when you have forecasted that there will be no cash inflows from the entrepreneurship project for a few years.
6. Passion for perks
The attractive perks also count! How will the fully paid annual holidays and comprehensive medical insurance for the family be funded?
7. Costly family
The above pay and perks become almost an imperative if you have regular fixed obligations.
I am not just talking of the wife with expensive tastes but the rent, the kids’ pricey school and college tuition and the hefty payments on the house and car (partly thanks to the wife insisting on these to compete with her peers and also because you value domestic peace).
8. Managing people
You have been an employee all your working life, and you have no idea how to lead a team at a small, unknown startup.
This is because you’ve been in corporate for so long that your high technical proficiency is not matched by your soft skills and emotional intelligence which remain at a low level.
Translation — you are crap at managing people let alone setting a vision and guiding a team to nail the vision.
9. Specialist to generalist
When you are an entrepreneur, you must be a jack of all trades, a generalist.
But, you’ve no idea how to market and grow a business because as an employee all this stuff was done by largely invisible humans in the marketing, PR, and sales departments of the companies that employed you.
10. The wrong mindset
You are mentally quite sensitive meaning you often lack confidence, commitment, control, and so on. You have a tendency to be shocked, angered, and/or disappointed quite easily and you also give up too quickly, all traits that are potentially disastrous for an entrepreneur.
Look there is no silver bullet that will magically destroy all these hurdles.
But, there may be a way.
You see long ago I studied under an obscure but incredibly wise Tibetan monk deep in the Himalayan mountains and after many years of grueling penance and deprivation he whispered in my ears the secret of….
Just kidding.
The truth is that I leapt from corporate to entrepreneurship and I faced many of the above hurdles and learnt by watching and doing.
The below are my brief tips to address some of the ten challenges I pointed out above, tips mostly gained from quitting corporate life and building a well-respected brand to a satisfying exit.
1. Adjusting inflows and outflows
Let’s talk about the worry that outflows may exceed inflows once you quit your gilded cage. To quote Charles Dickens in David Copperfield:
“Annual income twenty pounds, annual expenditure nineteen nineteen and six, result happiness. Annual income twenty pounds, annual expenditure twenty pounds ought and six, result misery.
”
I take it that you don’t want to be miserable.
So, the inevitable question is can you reduce your outflows or increase your inflows or do both? I bet the answer to the last two will be “you’ve got to be kidding me!”
Hence, we neatly divert to the first — cutting your monthly cash burn, to use startup parlance. Will you and your family be fine with a smaller house or less expensive vacations or moving to a cheaper city or attending less expensive schools? Or will they let out a scream that can be heard on Mars?
There’s no right or wrong answer to this. The question simply is how much you and your family are willing to sacrifice to get a shot at your dream.
2. Build a buffer
One remedy for the money problem is to hoard enough savings before you quit the corporate rat race for total freedom! (err… entrepreneurship).
If your monthly outgo is USD 5,000 and you don’t expect the new business to turn cash flow positive before 18 months, then you better have at least 36 months of cash outflow in your bank account because reality very rarely unfolds according to plan. Which means you’ve to start saving now till you reach the magic figure of USD 180,000.
Yes, its idle cash sitting with those greedy bankers but remember you’re building valuable insurance. One unintended benefit of this exercise is that you get time to refine your business idea and find a partner etc. so that by the time your ass of a bank manager calls you and says “Saar you’ve USD 200,000 in your fixed deposit account and that should not be lying in cash so might we interest you in a great mutual fund, utterly risk free and … ” you know you’ve enough in the bank to quit.
3. Test your idea
If you aren’t sure of whether the idea will work, take it for a test run while you are still an employee.
Which is what I did. From July 2008 till May 2009 my co-founder and I ran Genesis, the CFA prep business, as a side hustle. We were both full-time employees of our respective employers during that period. I found that:
• There was a big gap in the market.
• I enjoyed teaching students and was pretty good at it, gauging from the feedback I kept getting from students who were blown away by the quality of face-to-face classes.
• Because of the above the business was picking up — word of mouth was explosive, class sizes and number of batches were increasing, and so on.
So, in May 2009 my co-founder and I left our full-time jobs and joined Genesis as the Director and Managing Director, respectively. That’s probably the best career decision I’ve ever made.
4. Software solutions
It’s an issue if you are not a techie and the business won’t work without a big tech component.
The obvious solution is to either hire a CTO (full time or freelance) or if it is critical then make a techie your business partner. Each has its pros and cons.
Whatever the choice, the key here is that the techie (in addition to being a software expert) should be commercially astute — the ability to efficiently and effectively translate business requirements into code.
Because the history of startups is littered with examples of brilliant techies who can’t manage a business or manage people and had to leave or were kicked out.
We come to your ability to lead a startup.
This is a big topic that arguably deserves a book of its own (perhaps I should write one!). I am too lazy to get into details and since lazy people often have brilliant shortcuts, I’ll give you a few:
• Read a lot on entrepreneurship. From Zero to One and The Almanack of Naval Ravikant are my favorite reads but check out the others.
• Find a mentor or two. They’ve been there and done that and by talking regularly to one you may head off a nasty accident, provided you are willing to listen.
• Get a co-founder who complements you in both aptitude and attitude.
• This worked brilliantly at Genesis. My co-founder was quiet, low profile, serious, methodical, patient, focused on process, operations, and efficiency. I was high profile, engaging, popular, funny, spontaneous, obsessed with class quality, overall student experience, and effectiveness. This was almost a perfect match, but it was pure luck and it worked.
• Don’t leave it to luck. Make it intentional.
“Strategic quitting is the secret of successful organizations. Reactive quitting and serial quitting are the bane of those that strive (and fail) to get what they want. And most people do just that. They quit when it’s painful and stick when they can’t be bothered to quit.”
This piece is about quitting when you should, something that so many professionals in their thirties and forties and even beyond have yet to master.
Transitions involve quitting. Quitting something is what leads to transitions. So, I thought it’s perfect to include in this final section a write up on quitting.
Firstly, I have a masters in quitting in many aspects of life, so I know exactly what I am talking about. Let me give you a few examples. Please note that this is by no means an exhaustive list.
At 19 years, I quickly surveyed the marital landscape around me, saw that it was littered with average or miserable marriages, contemplated the trade-offs and decided to never get married or have kids. Strictly speaking it’s not quitting because that term indicates starting and then leaving. But, you could say I quit any plans to lead a conventional family life. I knew myself well enough even at that young age (at least in terms of relationships), hence I would count that as the best decision of my life so far.
At 31 years, I quit studying for the American CPA exams. I had bought the books and enrolled for the exam. My strong (but unsubstantiated) belief is that the AICPA still owes me $200 as refund for the exam I never wrote. Good decision as I had no plans to migrate to the US, Canada, or Australia.
At 34 years, it dawned on me that I was not designed to slave on for another 20 years for the slim chance of one day becoming God (i.e., Partner) at the Big 4 firm I was working in. I quit the mechanical and utterly boring and stressful world of audit to join industry. Good move that matched my values, traits, and skills with my new role in a small but fast-growing real estate developer.
At 39 years, I quit as executive director at a listed asset manager after 17 years of corporate life. I decided that being a CFO, Group CFO, or CEO of a large entity didn’t excite me. Another good decision that matched my values, traits, and skills with my new role as the co-founder and MD of a small but fast-growing financial training company.
At 43 years, I decided that running marathons — or any long-distance race — was not my thing and gave up the ambition of cracking a 4-hour marathon, a long-cherished dream. I found running utterly boring and that was also a timely move as long-distance running would have damaged my joints (especially knees). It can also cause joint-related problems in old age.
In several books, I’ve seen this referred to as Strategic Quitting or Strategic Underachievement. I’ll go with the former — it’s shorter and punchier.
On reflection I am glad I quit and have few regrets. On further reflection I thought I should pen the benefits of quitting and why so many refuse to quit when they should.
Ten reasons why you should consider quitting your job:
1. You don’t see yourself achieving your key career or life goals where you are now.
2. You are now past your mid-thirties; you have discovered your values and you have also uncovered that you are currently not living your values.
3. The original goal/s means much less to you now because they don’t make any sense in light of your new values. Important point — your values are likely to change as you age but your personality traits are less dynamic.
4. By giving up your job now you have free time for what’s more important to you.
5. There is so much you can experience, and quitting opens the gate to new experiences.
6. You value freedom at work and the current culture at work is of distrust and micromanagement.
7. You’ve stopped learning and learning usually turns you on.
8. You have enough money in the bank to sustain you in case you quit, take a sabbatical and explore alternative careers.
9. You are merely coping at work and hence you will never deliver exceptional performance. All coping does is waste time and misdirect energy. If the best you can do is cope, you’re better off quitting.
10. You are ready to be an entrepreneur.
You will note that I said, “consider quitting.” I am by no means implying that you should acidly tell your boss to perform an anatomically impossible task and then walk off humming the tune of “We Will Rock You.”
So why don’t most people quit? Here is why.
1. The missing compass effect
You have only a vague idea what your values are. Since these are unknown all you have is a growing sense of discomfort.
2. The stable income effect
You are well paid, and you think you can’t maintain your current lifestyle if you quit.
3. The Goldilocks effect
This is extremely common.
The job isn’t that boring or dangerous, what the company sells isn’t that toxic or shameful, the boss isn’t too annoying, and the colleagues are not such a bunch of backstabbers that you feel you must quit immediately.
Yet the job isn’t that exciting, what the company does is Ho Hum, the boss isn’t so leader-like, the colleagues aren’t that supportive, and it isn’t so great that you spring out of bed every morning all keen to show up at work for another brave attempt at changing the world.
It’s neither too hot nor too cold, hence the Goldilocks effect.
4. The promotion effect
You have been promised a promotion if you keep performing.
Since you’ve been an above-average performer so far, you know the promotion is near and don’t feel like walking away although in reality it’s more of the same and you are simply delaying the inevitable.
5. The status effect
Your business card and email footer have the impressive looking title and employer “brand” and that makes you look successful and respected in the eyes of parents, other relatives, peers, friends, clients, suppliers and, well, pretty much all of society.
6. The sunk cost effect
You have laboriously made your way up the corporate ladder, and you feel you have invested too much time and energy to just quit. This is despite the fact that it’s a job which you don’t even like and/or are not even that good at.
7. The dinosaur effect
You haven’t bothered to keep in touch with the many changes in your domain. Now you can’t be bothered to spend the significant effort to get up to date, something likely required if you change careers.
The alternative to quitting is coping. This is exactly what most do. You grit your teeth, think of all the points 1–7 above and muddle through yet another day at an unloved job.
Don’t spend time in the average zone which is what happens a lot of the time when you don’t quit your job for something better.
“One should waste as little effort as possible on improving areas of low competence. It takes far more energy and work to improve from incompetence to mediocrity than it takes to improve from first-rate performance to excellence.” — Peter Drucker
What is implicit in Drucker’s message (which Seth Godin picks up and makes explicit in his book The Dip) is that only excellence matters. Trying to upgrade yourself from incompetence (below average) to mediocrity (average) is what you do when you cope and muddle through. You do this so that you don’t get fired. But, this is often worse than useless because the time and effort spent on this upgrade is better spent on areas where excellence is within your grasp.
Let’s assume that you have tried everything at your current job, and nothing has worked and it’s time to go. Let’s also assume that you are one member of a vast demographic that I am quite familiar with — the CFA charter holder in his mid- to late thirties who has not been doing anything connected to the curriculum since he passed out X years ago and who now wants to change careers.
If asked on the recruitment process so far, you’d probably say:
“I have the detailed job description and had an hour-long discussion about it with the nice HR lady! Yes, the sell side Senior Equity Analyst role at a boutique brokerage is quite different from my last job in as a F P & A Manager but this has been my dream role ever since I got the CFA charter, and which is why I considered moving. Also, this is exactly the career I wanted when I started my CFA journey and is also the career which the CFA curriculum prepared me for when I finished Level III long ago.”
That’s not the way to think.
Because, before you switch careers you must ask yourself the below questions.
1. Are you fully aware of the nontechnical factors that are required to succeed in your new job?
You need to think of some of the transferable skills that I yakked about earlier in this book. The soft skills. The emotional intelligence.
Because if you want to be a successful sell side equity analyst, then you must understand that your job may involve the below activities (with related nontechnical skills in brackets):
a. As a sell side analyst, you will have a much bigger coverage universe compared to a buy side analyst who only has to cover his firm’s focus areas. This means churning out many reports under extreme time pressure (resilience).
b. You’ll need to listen carefully to what others say (management, clients, suppliers, regulators, etc.) and especially on what’s NOT said. You then have to write in such a way as to simplify tough concepts, deftly capture the essence of a complex, fast-evolving situation and yet in a way that is compelling enough to read. You need to keep first things first (the recommendation, target price, upside percentage) and believe and act with the strong belief that less is more (communication skills).
c. The ability to separate the irrelevant from relevant information, focus on the core issues, and connect the dots to get the big picture (analytical skills).
d. The ability to wade through mountains of boring text and numbers such as annual reports and conference call transcripts and not miss the slightest inconsistency or error (attention to detail).
e. You are in the sell side. Smooching institutional clients to win commission business may be considered part of the role (selling skills).
2. Are you fully aware of the technical factors that are required to succeed in your new job?
A lot of the time the boys and girls in HR have no clue about what you actually will be doing. Especially if it’s a small- or medium-sized firm where HR is running everything from cleaning to security to secretarial and is also staffed by junior folk. So don’t take the HR person’s word for it.
More crucially, they are probably hiring you not because you have the technical skills but because:
• You have the prestigious CFA charter and that will add a lot of credibility when the firm markets its services.
• You are cheap because it is considerably more expensive to hire someone with decent equity analyst experience.
Let’s go back to the equity analyst role. The technical skills you must master are financial accounting, financial statement analysis, business valuation, and MS Excel.
3. If you don’t have the skills required to succeed, can you pick these up?
You will of course shout “Yes!” But, hold on to your horses and ponder the below nuggets of wisdom:
• It depends a lot on your starting point on the learning ladder. The lower you are on the ladder, the longer and tougher it will take.
• Some skills are easier to pick up than others. For example, soft skills are much tougher to pick up compared to the technical stuff like accounting, financial analysis, Excel, financial modeling, and valuation.
• Within soft skills, there are varying degrees of difficulty. For example, learning to write and speak English fluently can be hard for many after a certain age. Cultivating emotional intelligence can be even harder — it can be done, but it’s often extremely difficult to “become” calmer, more tolerant, more tactful, or more empathetic.
• Also bear in mind that companies have limited budgets and patience. Most will want you to hit the ground running and only a few may give you some time to learn the ropes.
4. Does the next job or career involve deploying your top abilities and strengths?
Why? Read the Drucker quote above.
If your answer is “Yes” then the chances of being fulfilled are so much higher. There are few things in life as enjoyable and rewarding as working at a place where you are absolutely the best person for the job. Its highly likely that you will not only beat your previous job performance, but you will also beat the competition.
If not, you will feel like a square peg desperately trying to fit in a round hole and your odds of succeeding are greatly reduced.
5. Are you aware of the sacrifices required and are you prepared to make those?
A change of careers can get longer and nastier than you think.
Based on the talks I’ve had with my many coaching clients and former students and mentees; these are usually what you must be prepared for:
• Less popular employer.
• Because, as I wrote earlier only a small company will give you the break you want. That’s not great if you have a strong preference for “brands” and care about what other people think.
• Lower title
• You may go from senior manager/manager to senior analyst. Something to think about if you are still in “external validation mode” and bothered about how this will look on your resume or business card. You may also have some explaining to do if you change jobs in future.
• Smaller companies can’t afford the high salary, generous school fees, full medical coverage, the annual paid vacation, and so on for you and family that you are currently getting. This can cause friction in a family that’s used to a certain lifestyle.
• Change to a less desirable location
• The best opportunities may simply not exist in the city where you currently live.
• For example, I always tell anyone targeting a career in equity research or portfolio management to head to developed markets or large emerging markets (like India) and forget the UAE because these financial markets are way larger and more professionalized than the UAE capital markets.
• The big issue? Many CFA charter holders have been pampered by the super safe and comfortable UAE lifestyle and find it almost impossible to relocate from Dubai to the harsher realities of Mumbai or Bangalore especially with kids. If you think that’s an easy transition, think again.
• Losing your track record
• If you switch careers your track record up to now will be rendered almost useless as it may mean very little in your proposed career. True, it’s a sunk cost and hence irrelevant and you shouldn’t be biased but are you prepared to let that go?
By the way, it’s not enough to be aware. You need to imagine the details by expanding on each of my above narratives which I’ve told from 30,000 ft. high.
Moral of this story: Thou shalt not underestimate the sacrifices required.
6. Let’s assume you do manage to pick up all the key skills with great difficulty, endure all the above sacrifices etc. and you make it. Do you think the rewards will be worth the effort?
I recall reading about someone whose dream was to be a doctor. A mediocre undergrad student, his burning desire took a lot of time and effort, and he finally became a doctor in his late thirties.
But now that he is a doctor, he hates the job thanks to the long hours, lack of sleep, difficult patients, unending admin work, and so on.
Think hard about what happens when you achieve your dream role. If the payoff (in every sense) isn’t enough, then quit and focus on a better pathway.
7. Finally, has anyone else you know done this before?
If so, you have a model of how this might be done. That person may even guide or mentor you. At the very least you know it is possible.
If not, perhaps you should reconsider your transition plan now that you know it’s rarely or never been done.
Life at the top is quite different.
Now, that sounds like an obvious statement. But, that’s only for those who’ve been to the top. I realized recently that it’s not at all obvious to the many who aspire for leadership.
I was talking to a former student (let’s call him Dex) who I’ve known for the past 12 years. He was a finance director and was about to join a startup at a senior level. Just how senior I was about to find out.
We chatted for another 10 minutes, and he told me more. I knew the industry well.
Then it hit me.
Me: Yes. And admin. And HR. And marketing. And sales … It’s a CEO role. You’ve never done this before so it’s fantastic and I’m happy for you. But, you’ve never done this before so there’s a lot you must know and change. It’s not a technical role anymore like being a finance director and the buck now stops with you.
For the next 45 minutes, I ended up giving the world’s shortest leadership course (!) as we went through:
1. What questions he must ask before joining.
2. What being a CEO entails.
3. Specific attitude gaps that he must close.
4. The huge mindset change required.
5. The critical success factor.
6. Potential “political” problems.
7. Organization structure and hiring.
8. People he should speak to in his sector before joining.
1. Responsibility
It matters little what you are called (CEO, General Manager, Senior Vice President) because it’s quite likely you will be managing a P&L. This of course means you are responsible for revenues, costs, and profits of your unit (branch/division/business line/company).
Those three items are probably among the most important leadership KPIs at your unit and that pretty much sums up the seriousness of the job.
Career transitions like this (from technical to leadership) are extremely rare and must be seized without undue hesitation. They’re also exciting and potentially transformational and I’ve seen that happen. Don’t worry that you feel you are not 100% ready. No one is fully ready, and many leaders learn on the job.
But, such transitions can also backfire badly and end up with you quitting or being fired if you don’t know what you’re walking into. I’ve also seen that happen.
The boy scout motto is apt. Be prepared.
3. Move beyond technical
It’s quite tempting to tinker with your technical domain, which is also your comfort zone even after you are the CEO. That is a mistake as it will suck valuable time and effort away from your mandate which is to run and grow the company.
So, stop worrying about your area of expertise and focus on running the company and its many moving parts. When I was running Genesis this is what I had to do — stop obsessing with my domain (teaching CFA prep and CFA candidates) and focus more on corporate marketing and sales.
It isn’t easy to step outside your comfort zone but that’s what leadership is often about. That’s also what I advised Dex — delegate your domain to someone else and think and act like a CEO.
I asked Dex who has the authority to hire staff and to sign cheques. Did he require the approval of the sole shareholder for this and other significant matters?
He thought he had the sole power but wasn’t sure. He hadn’t asked.
When you have one or a few investors it’s quite tempting for them to interfere not just in strategy but also in day-to-day affairs like hiring and firing. You can’t tell them not to — it’s their business after all — but it’s critical to clarify up-front. In some cases, you may even refuse to take up the job if it means you don’t have the autonomy you want. I know I wouldn’t join if I didn’t have the freedom even if the pay, title, and so on were extremely attractive.
5. Get a good team
As the Top Dog, you may have the enviable and invaluable liberty of picking who you want to work with from top to bottom. And, if you don’t you should insist.
I say it’s a rare privilege that must be used to the hilt. Because if you build a good team (I am referring to the people who report to you) then life as a leader will be so much easier.
I have become a fervent believer in picking the right people. When I ran Genesis, we eventually ended up (7 years after starting the company!) with a solid second line, with a manager/senior manager looking after:
• Marketing
• Retail sales
• Training
• Operations
• Human Resources
• Accounting
It would have been almost impossible to have delivered the excellent quality and superior financial results that we did without this team.
What do I mean by “good’ and “solid”? Each of the above managers was not only an expert in his/her area, but they were also self-regulated (required little or no management), worked well together and showed exemplary ownership and integrity.
6. Manage the politics
When you are a junior, you don’t get involved in the power plays. You just deal with mostly your boss and a few colleagues and that’s it. You usually don’t have the headache of dealing with multiple outside parties.
But, once you sit in the C-suite, there are more stakeholders to connect with, know well, keep informed, get the approval of, occasionally bow before, and so on. You may have to deal with, inter alia:
• Investors
• Board members (current and former)
• Senior executives (including those who lost out in the CEO race)
• Key clients
• Key suppliers
• Consultants
• Lawyers
• Joint venture partners
• Auditors
• Tax authorities
• Ex-CEOs
• People close to the above (relatives, friends et al.)
Each of the above has a unique goal (expressed formally or not) and it requires considerable skill, patience, and executive presence to navigate successfully through these.
But, first know who all you have to deal with.
7. Have the right mindset
Put three cups of P&L management in a pan and boil. Throw in several slices of already fried demanding stakeholders. Turn up the heat and stir firmly for what seems like an eternity with politics. Switch off the heat. Garnish with incompetent and indifferent team members. Serve when cooled.
Result? You have the extremely spicy dish called Stress Biryani that few can stomach.
It requires an enormous amount of mental toughness and emotional intelligence to handle all this. Dex was prone to stress and overthinking even as a technical expert. This new role could amp up the stress by a factor of 10 and I was waving a big red flag in front of him so that he could put strong guard rails in place. Otherwise, this could easily derail his foray into leadership, and this was the biggest risk factor.
Moral — If you insist on being a Chef, be ready to take the heat. If you can’t stand the heat, don’t enter the kitchen.
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