Startup Confessions: 5 Lessons I Learned My First Year as an Entrepreneur

In 2011, I started my first business — a health and fitness media startup called Greatist. I had no real clue what I was doing.

Since launching my company a lot has gone right — and quite a bit has gone wrong.

A year ago, I’d never:

1. hired someone,
2. fired someone,
3. incorporated a company,
4. spent days doing accounting work in Excel,
5. signed an office lease,
6. saved a crashing website,
7. negotiated a potential acquisition, or
8. been responsible for six people’s paychecks.

But these types of things — operations can always be figured out.

Instead, the biggest challenges I’ve overcome in business have been personal. In fact, dealing with personal challenges is much harder.

When I started my business, I had never been so busy, so behind, and so unsatisfied with how little I accomplished with a mere 24 hours in each day. At the same time I had never been happier, more optimistic, and more excited for what I knew could be achieved. I could genuinely say that I love every second of what I’m doing.

Through my challenges — adapting to and navigating small business ownership, here are five important lessons I’ve learned.

1. Starting something — for the first time — is really, really hard. 

Think back to the hardest thing you’ve ever done. Then imagine that “this thing” was the most important thing you’ve ever done. Now reflect on whether or not you had absolutely no idea what we’re doing (imagine that you were completely clueless).

No matter what you think about entrepreneurship, know that it is not easy. If you think starting a business is easy – you’re wrong. Becoming an entrepreneur has been way harder than anything I’ve ever done.

I love that challenge. A startup is a to-do list with infinite scroll. It’s true that it’s never been easier to start a startup, but that doesn’t mean that launching a startup is remotely easy.

2. Sometimes you have to make mistakes for yourself. 

There’s an unbelievable amount of information on the web about starting a business. But regardless of how much information you absorb, you’re going to mess up anyway.

I came to accept the fact that I’d make a lot of mistakes. For example, knowing that you should fire someone immediately who isn’t working out because they’re hurting your team’s culture is much easier than acting on it. I knew, but I didn’t really know until I felt the bitter taste of a mistake in my mouth.