What They Don’t Tell You About Being an Entrepreneur - Part 1

Jason Sosa
5 min readSep 19, 2016

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It is the best time to be an entrepreneur. It’s by far more rewarding to bet on yourself than the hourly pay that benefits others with your energy and efforts. If you’re young, a fresh out of school grad, or you’re just exploring the possibility of being an entrepreneur; there is a mindset to be aware of before making the leap. Especially if you are considering a tech startup.

Being an entrepreneur is a decision to not choose the default framework for an average life. If there’s one word to define what being an entrepreneur is really about, it’s “sacrifice”. You sacrifice certainty for variety, comfort for discomfort, familiarity with the unknown. Before you jump in, make sure you understand the mindset of what it’s like day in and day out to be an entrepreneur and know what you’re getting yourself into.

This is the un-romanticized version of being an entrepreneur that gets omitted from “overnight success stories.”​ It isn’t meant to make you feel warm and fuzzy. It lays bare a taboo topic that others experience but rarely speak about.

1. It’s harder than you think — but it’s worth it

Examine your motives. If you’re looking to be an entrepreneur because you want to get rich, think it’s glamorous, want to be the next Mark Zuckerberg after watching the movie “The Social Network,” then you’re doing it for the WRONG reasons.

There are countless articles that explain all of the external strategies such as how to prepare your pitch deck, what questions to ask investors, how to validate your ideas, but aside from those things — the biggest challenges you’ll face will be with yourself. Your self doubts, your internal fears, inadequacies, and limiting beliefs.

Many would-be entrepreneurs imagine their company name on t-shirts, tech blog headlines, and popping bottles of champagne when things go well. But it’s also losing sleep at night while you feel your esophagus burning from inside your chest. It’s sitting in your car as you anxiously await a VC meetings on Sand Hill Road. It’s lots of travel hoping to land the big deal. Like a roller coaster ride, the highs come with the lows. It’s both sides.

“Being an entrepreneur is like jumping off a cliff without a parachute — then assembling a plane on the way down.” — Reid Hoffman

In the early days, it’s fun. Over time your relationship with your startup will become complicated. It intertwines your identity, interests, reputation, and social circles into your profession. It becomes easy to get consumed, and personal relationships may suffer. Your complete focus will be on your company, and everything else will be second place, even if you rationalize it to yourself as otherwise. You’ll get gray hair early, experience lots of rejection, and at times fail miserably. Eventually, you’ll get used to it, toughen up, and find a rhythm. You’ll learn to use failure to your advantage as a strategy to de-risk new ideas. As your skills leapfrog over others, it can be an isolating experience and it becomes harder to have normal conversations. Most everyone, including your family, will think you’re irrational, irresponsible or hopelessly impulsive.

Do you have entrepreneurs that you admire? Few founders have achieved legendary status. Entrepreneurs such as Steve Jobs, Elon Musk, and Mark Zuckerberg are idolized in tech blogs, books, and movies. However, many articles disproportionally favor the perceived overnight success and fail to mention the decades of effort that led up to it. Stories often don’t adequately reflect the isolation, the rollercoaster ride, the debts, and the many sacrifices.

The goal should not be to emulate your heroes, but to learn from them.

Everyone you meet in startup land will tell you they’re ‘killing it’. No one wants to tell you about the nightmares, the indigestion, the political power struggles, fights with investors, and the stress and anxiety of holding it all together. The pissed off wife/husband that never sees you and the guilt you feel when you should be out ‘having a good time’ yet feel you should be working instead. Founders don’t talk about this stuff with investors, their board, their spouses, or even close friends.


It’s like a man riding a lion. People think, ‘This guy’s brave.’ And he’s thinking, ‘How the hell did I get on a lion, and how do I keep from getting eaten?”

2. Mindset

Now, after knowing all that, and I haven’t scared you off — then you’re probably just crazy enough to be an entrepreneur. You must be insanely motivated! It has to be in your blood. Few career paths allow you to grow more personally, emotionally, or professionally than being an entrepreneur. Until you jump out of the proverbial “plane without parachute,” you won’t know what you’re capable of. For an entrepreneur, mindset is everything. It’s your ability to convey confidence to investors and it’s how you get early customers to trust you. If you focus on all the external factors but neglect to prepare your own mindset, you’ll continue to struggle convincing yourself that you need the latest business book, strategy or productivity tool. Simply believing in yourself goes a long way. This is easy to understand intellectually, but much harder to practice.

Entrepreneurs calculate risks, but the difference is that they experience more pain from the possibility of regret. For people with entrepreneurial blood coursing through their veins, the thought of being 80 yrs old in a rocking chair thinking ‘I shoulda’ or ‘I coulda’ is a fate far worse than death. Life is too short to live with regret, exist without a purpose, or to be stuck doing something you hate every day just because you ‘gotta pay the bills.’ If you’re going to do this, make sure you’re mentally all in.

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