Don’t Let These 4 Fallacies Derail Your Entrepreneurial Success

Being a CEO, entrepreneur, or self-employed creator doesn’t make you immune to this career-dampening mistake.

Shoveling dirt onto my dad’s descending casket was the liberating reality adjustment that ejected me from the fear-propelled orbit that keeps so many tethered to the infamous rat race. I went to class (just like any other day), he died of a heart attack mid-lunchtime basketball game at work, and I returned to class within a few days of the funeral. My whole world changed, yet everything stayed eerily the same — and once the customary grieving period was over, I was expected to return to normal as well.

But I didn’t. A stark encounter with death — or any abrupt, unexpected life change (for the better or worse) — can do more than shake you to your core; it can reshuffle your values or erode them altogether. While my dad’s death marked the start of my bold, risk-taking, entrepreneurial mindset — the one that encouraged me to stray outside my “lane”, the impact of those jarring, mindset-transforming events doesn’t always last forever. Within a few years, I’d been sucked right back into the title-worshipping, accolade-seeking grind.

Whether you’re an employee, a CEO, or an aspiring creator pouring over a dozen articles titled “How to Make $XXXX in Y Months”, selling out and losing your way may be the sneaky beginning to an unpleasant end.

The fallacies about owning your business (or your time)

When I first stepped foot in my bulge bracket investment bank’s highrise for an interview backdropped by panoramic city views, I was riddled with fear. That fear didn’t go away once I got the job, went through training, or made working in finance my 24–7 gig. That lack of freedom was exactly what I aimed to escape when I set sail for a less conventional entrepreneurial path.

Little did I know, freedom (or a lack thereof) and paralyzing fear aren’t necessarily the fault of one job, one boss, or one career. Some of us may stumble right back into the same shackles we hoped to escape as we define the “new normal” in our pandemic-disrupted careers. I was one of them — and I messed up big-time.

Heading into 2020 and 2021, I had multiple irons in the fire — as I usually do. Some took off, some fizzled out, and others popped up out of nowhere, forging a life of their own, to my utter surprise. However, I’ve been confronted with some realities that have shattered the common fallacies many hold about owning your business — or your time:

• Fallacy 1: Running a business is liberating because you don’t have a boss counting your hours or determining your pay and employment status
• The truth? Running a business can easily make you a slave to your customers, who may wield far more power over your earning potential than any 9 to 5 boss ever did
• Fallacy 2: Achieving business success is a huge motivator and a vote of confidence
• The truth? Achieving your highest sales month drudges up unexpected feelings of fear, uncertainty, and insecurity as to whether you’ll ever do so again
• Fallacy 3: Working for yourself is fulfilling since you’re building your own empire
• The truth? Fulfillment doesn’t just come from ownership; it comes from the process and impact. In my experience across various businesses — and working and speaking with hundreds of entrepreneurs — fulfillment has much more to do with what products or services you sell than your sales alone. There are countless people making bank selling widgets on Amazon who are bored, stressed, and seeking an exit to a more fulfilling alternative. In fact, many of them are listing their businesses for sale as we speak…
• Fallacy 4: Traditional employment is scary because you live and die by the praise of a boss, a company budget, or a good or bad quarter
• The truth? Entrepreneurship is even scarier because the ups and downs in your industry may come without warning, and you likely won’t have a severance package to bail you out in the downturns

After debunking those four fallacies, you might think I’ve leaped to the dark side and have waved my love of startups, business, and entrepreneurship goodbye in exchange for a cubicle and a new LinkedIn headline. Not so. I love the geographic and time freedom an entrepreneurial life has afforded me, and I wouldn’t give that up so easily. However, I have taken a closer, more critical look at the variety of ventures on my plate — and I’m using a different yardstick than ever before.

We’ve all heard of ROI (return on investment), but what about ROE (return on enjoyment)? Listen, as a reformed “numbers person”-turned-entrepreneur, I know revenue and profit matter; we all have to eat, right? But trading an unpleasant 9 to 5 for a similarly unpleasant, even more stressful, less certain business — just to say you own it — doesn’t necessarily make sense either.

Over the past couple years, so many aspiring entrepreneurs, freelancers, and self-employed creators have buried themselves in ten million simultaneous revenue streams, 48 social platforms, and 100+ hour workweeks in the name of escaping the big bad job. But sometimes more isn’t better; it’s just a fast-track to burnout. Particularly if you don’t thoroughly enjoy the day-to-day process (or the impact the venture has on the world or your audience).

As someone who’s experienced it firsthand, I can guarantee you watching sales notifications slide into your email gets old — especially if you don’t really care about what you’re selling or to whom. The less you dread your day-to-day business operations, the less likely you’ll fizzle out before you achieve long-term outsized success. ROI may be the immediate measure of success, but ROE is a measure of longevity. Just because you can make $100k one month doesn’t mean you’re on track for $1.2M run-rate revenue. But the more enjoyment you derive from your business’s core operations and mission, the more likely that $1.2M will be in your future down the line.

The demotivating risk of success

So many of us flock to entrepreneurship as a means of escape. We’re escaping the favorites-picking boss or the underpaid role or the industry we’ve grown to despise. When you’re running from whatever (or whoever) you’ve deemed as the “big bad wolf”, any (and every) pair of open arms that don’t have claws and fangs present seem inviting. It could be a lion, a tiger, a bear — oh, my! But at least it isn’t a wolf…

That’s the danger of treating your entrepreneurial or self-employed journey like the welcoming savior rescuing you from the deadly clutches of the 9 to 5 you so narrowly avoided: You romanticize your venture, deciding no matter how difficult (or unenjoyable) it gets, it must be better than the alternative.

Unfortunately, that scarcity-based mindset urges some entrepreneurs to cling tightly to businesses, clients, or revenue streams that aren’t really serving them (at least on an ROE basis). Soon enough, those entrepreneurs may find themselves slaves to a business they don’t recognize or enjoy — that might pay the bills, but offer little more.

This year, I had a stark wake-up call when I faced a strange, conflicting scenario: I achieved a goal I never thought possible, while one of my ventures began to drain me, underperform, and suck time away from some of my other higher-ROE endeavors. All the while, I found myself falling out of love with that venture and in love with another one. The venture I fell in love with is one I’d told myself time and again — for decades — wasn’t financially viable. But there it was, rivaling (and sometimes outperforming) the other venture’s income! But remember, this isn’t just about money.

Once I achieved that reach goal, I realized I’d bought into a lie. The lie was that I had to continue operating the venture that made me miserable — despite its declining ROI (and negligible ROE), simply to justify my positive achievement. But I didn’t.

If you have a goal — whether it’s financial, location, recognition, impact, or other — you don’t have to commit to a lifetime of frustration, suffering, or stress to pursue and achieve it. I told myself I wasn’t allowed to be happy about buying a house because one of my ventures was having a down month or two. I robbed myself of the joy I should have had — that we should all have — by enjoying the process and the outcome, even though it wasn’t the one I’d envisioned (from the venture I’d expected).

Don’t take the wrong lesson away from 2021

If 2020 and 2021 have taught us anything, it shouldn’t be that we can all make money online. We should have known that back in 2016. Instead, these disruptive, transformative years should be teaching us that we’re allowed to question the journey and tailor one that works for us, that we enjoy — and that journey can be malleable, diverse, and subject to change with the times, the industry, and our own preferences. Anyone with a calculator or access to Investopedia can learn how to calculate ROI. Only those who take a step back and reassess from time to time will be thoughtful enough to calculate ROE.