Read This if You Feel Like a Worthless Wannabe CEO

Read This if You Feel Like a Worthless Wannabe CEO

9 boardroom confessionals your successful entrepreneur friends wouldn’t dare admit.

Read This if You Feel Like a Worthless Wannabe CEO
Photo by René Ranisch on Unsplash

As an entrepreneur who’s advised and helped thousands of others start and grow their business — and someone who runs the country’s biggest youth entrepreneurship accelerator — I’m undoubtedly a huge fan of building businesses. However, I diverge from most overzealous entrepreneurial influencers in one regard: I don’t believe in sugarcoating the journey.

Call me a pessimist, a buzzkill, or just someone who’s bluntly honest to a fault, but I believe one of the gravest tragedies in today’s digital world is the lack of transparency around the valleys that befall the people who appear most successful online. As a firsthand observer to countless entrepreneurs’ behind-the-scenes journeys and the front-seat driver of my own, I’d like to shed some light on the thoughts, concerns, and questions that vex and consume “successful” entrepreneurs and CEOs.

If you feel like a failure, a wannabe, or an entrepreneurial drifter still seeking your footing, welcome to the boardroom confessionals 99% of your peers go to great lengths to conceal.

Some mysteries are heart-pumping thrillers you voluntarily turn on and turn off; business, however, injects a costly consequence into each month’s mystery: Next month’s sales are anyone’s guess, and the bigger you grow and increase your respective burn rate (expenses), the higher the sales number you’ll need to hit to clear a profit.

Unless you’re running a business overflowing with long-term contracts and recurring revenue (real estate for the win, along with subscription toilet paper), each month can feel like starting over. No matter how automated your marketing or how large your profit margin, there’s no guarantee your lead generation engine will accumulate the same number or quality of prospects nor that your conversion rate will remain steady or increase.

The mystery of future income is easily one of greatest nagging and ongoing fears most entrepreneurs shoulder, and its the number one uncertainty that can drive them back to their 9-to-5, more grateful for stability than ever.

When financial uncertainty or a reputation-lambasting review from an unhappy customer nearly drives us to quit, one even scarier reality may stop us in our tracks: employability — or lack thereof.

One of the greatest benefits of entrepreneurship is the breadth of skills and experiences we accumulate and master; unfortunately, breadth doesn’t always make whittling that experience down to one best-fit job any easier. By being so unique and diversified in our entrepreneurial skills and expertise, it can feel daunting and difficult to mold ourselves back into the corporate box a traditional employer may be hoping to fill.

These are the thoughts that run through our heads as we contemplate what, if any, type of job we’re even qualified for:

  • I built a tech product, but I’m not really technical enough for a tech role…
  • I run my company’s marketing, but that doesn’t qualify me to manage a sales team…
  • I’ve created our financial projections, but I have no formal education, so a finance role seems out of reach…
  • I have successful experience scaling companies in my industry, but that doesn’t mean I know how to growth hack another industry…

While I still believe entrepreneurship is undoubtedly additive to a person’s market value and employability, in the depths of our despair, we can feel like corporate misfits who are downright unemployable, thanks to the confusing mishmash of eccentric qualifications littering our resumes.

Though we’d never tell you, many of us contemplate the tempting idea of cashing the heck out and running away.

We contemplate selling when times are good, in case this is the peak and the smartest exit opportunity. We contemplate selling when times are bad, in a desperate attempt to squeeze some cash out of a venture we feel is deflating before our eyes. We contemplate selling when an internet troll is mean to us, trashes our company, or threatens to badmouth our business to their giant social circle — despite never having purchased our product or service.

Then, a sliver of curiosity wedges its way into our brains, perplexing us further:

  • What if no one will buy the company, and I’ve built something unsellable?
  • What if I sell just before our next biggest month or season?
  • What if after selling I can never recreate a business this successful, and I gave up my one and only golden goose?

Then, we wait, shoving that cash-out temptation far into the back of our minds, deciding no decision is better than a rash one.

To this day, my biggest month in business wasn’t my happiest. As the sales poured in and the dollars stacked up, my anxiety heightened. I worried what we all do if or when we experience an abrupt outlier or rapid surge in growth: What if this is a one-hit-wonder?

What if this is unsustainable? What if this is my lifetime peak? What if I can never beat or even reach this again? Can I even take credit for this success, or was it just luck at play?

The worst part? Sometimes you’re right. For the vast majority of companies, every month can’t be your biggest month, and few — if any — businesses grow exponentially forever. Thus, while the good times might look good from the outside, from the inside, they’re evocative of our biggest insecurities and our greatest vulnerabilities.

If you heard the conversations entrepreneurs have with themselves and their closest confidants, you’d be shocked at how unfocused they might sound. Here are a few of the ideas I’ve personally tossed around and heard mulled over by successful CEOs in my circle:

  • I should just buy up a bunch of multi-family properties and rent them for stable cash flow
  • I should have been a plastic surgeon; they make so much, plus I’d have the credentials to start a beauty product line
  • I should live in my garage and rent out my house, so I could pocket the rent and buy another cash-flowing asset
  • I should convert my garage into a commercial space and rent it out
  • I should buy that mobile food franchise

That’s just a tiny smattering of the considerations I’ve heard successful entrepreneurs in my circle voice out loud. These thoughts came from people running profitable companies, some who own multiple businesses and properties. Still, their wandering eye has led them to believe there’s greener grass elsewhere, though they may be time- or financially-constrained from fully exploring it.

Even if your business is kicking, profitable, and growing, after a certain amount of time in the same industry, you start to see its cracks and crevices. Likewise, you may be drawn towards other seemingly easier, less risky, or more lucrative ventures that catch your eye and divert your focus.

They say humans can manipulate your emotions, and while that may be true, no human has ever come close to inflicting the emotional manipulation my company’s sales has. While it may be my fault, I can assure you I’m far from the only entrepreneur who’s let their sales and business success (or lack thereof) dictate their mood and happiness.

I’m not suggesting that entrepreneurship is all about the money, but for many business owners, revenue and profit numbers are the one objective way to peg their success and progress. While you should never hang your self-worth or happiness on money or your career, it can be very hard to separate your identity, confidence, and security from the current wellbeing of your business.

So many public-facing entrepreneur and CEO peers of mine would admit — only behind closed doors, or at private dinners with a few close friends — that they make it look easier than it is.

  • They don’t tell you (the public) when their ads get rejected.
  • They don’t tell you when their payment processor nearly shuts them down two days ahead of a pre-planned marketing collaboration.
  • They don’t tell you that going from 5 to 100 customers took two years or that they spend thousands to stay afloat beside deep-pocketed, ad-loving competitors.

Furthermore, here’s the truth these entrepreneurs have admitted to me but would never tell you: They feel that they have to make things look all-rosy all the time. They wouldn’t dare share their weaknesses, concerns, or pitfalls with customers, since they wouldn’t want customers to lose hope or faith.

In other words, whether you want to be a public figure or just anonymously run a thriving business, once your company is live for the public to see and patronize, entrepreneurs feel protective of that reputation. They don’t only show the highlight reel to invoke jealousy; they do so to preserve and defend the precarious business they’ve built. If they show you the cracks, they’re afraid you (customers) will flee, anticipating the avalanche to follow.

Some people say knowledge is power, but it can also be a curse. At some point, you may find that you know too much about your business, the evolution of the industry, the changing customer needs, or market climate to feel optimistic about its long-term prospects. This curse of knowing too much can put entrepreneurs in a dilemma-filled mental prison questioning your next best move:

  • Do you stick it out to see how long you can survive?
  • Should you secretly start building up an escape plan with alternate ventures on the side?
  • Is there a way to improve, tweak, or pivot the business to capitalize or weather the future storm and come out the perpetual winner?

While the worries of next month’s sales and profitability can weigh heavily on an entrepreneur’s mind in the near-term, there are greater overarching fears that may second-guess their every next decision and make each day feel like a countdown to an uncertain end. This mental angst is what drives so many entrepreneurs away from complacency; we know too much to believe the status quo prevails forever.

Whether you’re months, years, or decades into your entrepreneurial career, there’s one lingering thought buried deep in your subconscious that may rear its head from time to time: Am I making the best possible use of my time, career, and resources?

Every choice we make has an opportunity cost, and entrepreneurship is no exception. With every dollar I put into a new venture, would I have been better off putting it into the stock market, alternative assets, crypto, real estate, or what have you? With every hour or day I sink into one of my businesses, would I have been better off learning a different skill, getting another highly marketable degree, or transitioning my skills into a high-paying job?

Unfortunately, like any career or life decision, entrepreneurship requires a high enough degree of faith and conviction to ensure those trade-offs and what-ifs don’t become lifelong regrets. If your business is precluding an even stronger dream or goal, perhaps the opportunity cost may be too much to justify. The great thing about entrepreneurship is you can always return to it even more equipped after each career deviation or industry exploration.

Go to Publisher:

Entrepreneur's Handbook – Medium

Author: Rachel Greenberg