Entrepreneurship is the coolest kid in class and you can’t spend much time in the business world without being exposed to it in some shape, way or form.
These days, everyone’s an entrepreneur — including your broke cousin living on your couch reselling cheap electronics on eBay.
Largely seen as a status symbol of people living passionate lives and breaking free of the corporate prison — rarely do the hard truths of entrepreneurship make it to the light.
The truth is most entrepreneurs are dying to tell someone their struggles, yet remain silent for fear of being judged, looking like a fraud or hell, simply self preservation.
In a world of nonstop Instagram I’ll Teach You How To Make Six Figures Instantly it’s important to look at the other side.
In this post, I’ll share 6 secrets most entrepreneurs won’t tell you and how they may help you be realistic with your expectations on your own journey, plus an action step to deal with each.
There’s a sense that they can’t talk about it, that it’s a weakness or a shame or something. (inc. magazine).
How Entrepreneurship Became Cool
I’ve always felt the entrepreneurship label should be earned, not self annointed.
Meaning, if someone wants to introduce me as an entrepreneur, that’s cool — but even after launching my brick and mortar fitness business, it felt odd to call myself an entrepreneur.
There’s no secret the rise of entrepreneurship has been meteoric since the 70’s — according to the Kauffman Foundation, an entrepreneurship nonprofit, every month of the year welcomes 530,000 new business owners.
I remember the day I forced myself to get fired from my corporate job because I simply didn’t have the balls to face the music if I had quit…
And damn, that felt amazing — free, abundant and just the right of exhilarating liberation.
These days, with large personalities like Gary Vaynerchuk, Grant Cardone, James Altucher and countless others, everyone wants to be an entrepreneur…it’s the new American dream.
And that’s fantastic, in so many ways — for people’s creativity, fulfillment and our economy.
As awesome as it all is, here’s what’s really happening.
We’re On A Nonstop Rollercoaster
Entrepreneurs base a lot of their self worth on the current state of their business, which is always fluctuating.
This happens at a micro and micro level — meaning, day to day fluctuations have a severe impact on our moods, emotions and how we feel about ourselves.
Brad Hart, investor and strategist, explains:
One day you’re king kong, next you’re one of those kong chew toys. One day you’re the windshield, the next you’re the bug.
Since emotional states are highly transient to begin with, coupled with the fact that a new, urgent problem can come up at any moment — many of those who surround entrepreneurs can can fall victim to these never ending emotional storms.
Sometimes, when you’re deciding on filling your gas tank or grabbing food the rest of the day — you don’t know whether to cry or laugh.
Asking an entrepreneur how their day is going is a truly loaded question and we’re conditioned to tell others we’re fine — many times, because we feel they won’t even understand.
Furthermore, it’s almost as if we don’t want to rock that boat — I’ve always wondered if it’s fair to even do so.
Tim Askew, a CEO who wrote the article “The Peculiar Loneliness of Entrepreneurship” expands:
They truly cannot understand the unique frisson of terror that many of us wake to every day as we rise to try to methodically slay our individual business dragons. And even if they could understand, is it really fair to burden them with our existential anxiety?
ACTION STEP: If you’re experiencing rollercoaster emotions, start to take planned breaks to separate yourself from your business in your daily and weekly schedule.
We Can Never Truly Shut Our Minds Off
I did my best, I truly did…meditation, fitness, walks in nature — yet it never fully worked.
Hell, I even spent an hour a week in a sensory deprivation tank, floating in tens of thousands of pounds of epsom salt in a futuristic, egg shaped bathtub.
As entrepreneurs, especially those who run teams and have full time employees whose livelihood depends on them, it’s a 24 hour mental whirlwind.
Our minds are always thinking…
What if our sales drop and I can’t make payroll?
What if we lose our biggest client and we’re late on rent?
What if a competitor opens up a few feet away or Facebook changes the algorithm?
It’s an exhausting process that can eat away at your mental and physical energy every single day.
I asked my buddy Kolby Kay, who runs The Healthy Primate and seems to launch a new business every week, to describe a typical day:
Scared, angry, frustrated, excited, happy, anxious — that’s all before lunch. This is hard and you have to know going in that you are going to be broke, tired, hungry and alone.
Yet when it all clicks and you can help someone, build something and make your first dollar — that entrepreneurial high carries you, at least past lunch.
ACTION STEP: Find your outlet, whether it’s a fitness session, walking in nature, journaling or being social — make this you time non-negotiable.
We Often Question It All
In closed doors conversations with almost any creator I know, they question what they’re doing all the time.
Especially those who have their back up against the wall or in the startup phase where belief is the only thing driving you forward, the doubts are ever present.
This questioning can wreak havoc on you for countless reasons, including feelings of being labeled a failure or not as dedicated to your craft as you’d like others to think.
Even once markers of success are achieved, entrepreneurs suffer from high levels of imposter syndrome — or the fear of getting found out.
Admitting to others that you do question your path and business model is absolutely normal and should be shared openly, instead of simply faking that you have unlimited courage and conviction.
ACTION STEP: Acknowledge that everyone questions their life path at times and don’t beat yourself up about it, discuss it openly with people you trust or in a mastermind setting.
We’re Lonely
There was a point when I was building my fitness business that I simply let all social connections slide that didn’t serve the direct goal of business growth.
Hell, even the ones that may have grown my business I didn’t pay attention to because I was so laser focused.
This wasn’t a grand plan, it started with a slow drip, declining invitations — then becoming my new norm.
I’d pride myself on working on the business on early mornings, sundays, weekends, national holidays — grinding away on a new marketing plan or working the financials.
Which means…long periods of isolation, which are never good for the psyche.
At some point, I came to the realization that more was not better…the proverbial glass of water was full and spilling over.
Part of this was simply finding it difficult to connect with people in my current social circle who I could open to about the frustrations of managing a team, having competitors open up 10 feet away and other intricate business stressors.
ACTION STEP: Do at least two social activities a week and have a group of like minded people you can share both strategy and frustrations with.
We Fantasize About Your 9–5
I’ll admit this openly: I often fantasize about doing some of the work my friends are doing.
I quickly come back to the realization that I value freedom and independence too much, but the thought still crosses my mind.
Sure, they may not be enthralled by it and are being micromanaged with endless office politics, but there’s something alluring about being able to clock in, and clock out — knowing the livelihood of the business is on someone else’s mind.
While 9–5ers may be fantasizing about the entrepreneurial freedom of being able to travel and work remotely, many entrepreneurs look at steady paychecks, less time and energy investment and AMEX expense accounts as a pretty sweet deal.
ACTION STEP: The grass isn’t always greener and there is nothing right or wrong about your chosen path as long as it’s important to you. Make a list of 50 benefits of what you’re doing right now.
We’re Often Seen As Unemployable
After I moved on from my brick and mortar fitness business, I had already started building a new business in the online space.
Yet, I wanted to test out the waters and see what was out there.
As Gary Vaynerchuk says, there is no shame being a #2, #3, #11 or #117 of an amazing organization.
In other words — once you’ve been #1 you understand that it’s a ton of pressure.
I started to look for employment in various firms, always making sure they were either startups or had a sense of entrepreneurial spirit within their core values.
I’d have these unbelievable, riveting conversations, often with CEO’s or close to — yet never hear a call back.
One day, after applying to run digital marketing and sales for a startup in Orange County, California — I had developed a pretty cool relationship with the COO.
He basically said…
Tommy, you’re a perfect fit…yet, our team thinks you’re unemployable. What we mean is that we don’t see you staying here longer than 12–18 months before you run off and start your own deal again.
I was blown away…yes, it was an amazing compliment but at the same time it was a stark reality:
I was in too deep, and I may never get out.
If you survive on your own for too long, you become unemployable. Well, maybe you can jump into something else entrepreneurial, like somebody else’s startup. But normal employers won’t want you — Tim Berry
ACTION STEP: It may be too late for you, seriously. However, if you are looking for an opportunity use your current network and be okay asking for help, honing on organizations who value your entrepreneurial skillset.
So, What Now?
Entrepreneurship is an amazing, riveting world that has provided me with endless experiences, skills and learning that will last me a lifetime.
I’ve been able to do everything from marketing, HR, staffing, leadership, client services, events and everything in between — helping me understand life at a deeper level than any other alternative.
And the freedom, there is nothing like setting your own schedule and creating on your own — that is priceless.
Yet, it’s important to be real and honest in a world where everyone wants to be an entrepreneur and the dream has never been sold more aggressively.
Talking openly about our struggles outside of own circles is the first step to being real about our own challenges and creating a culture of honesty, support and helping others do the same.
