Entrepreneurship Hurts Like Hell

Lately, I’ve been asking myself, “How much should entrepreneurship hurt?” Because sometimes, entrepreneurship hurts like hell.

I agree 100% with Kermit the Frog when he says, “It’s not easy being green.”

Every time someone asks me where my office is or how many staff members I have, a little piece of me wants to curl into a ball and admit that I am nothing.

That’s obviously not true. I do have a team, and we all remotely — but I know the person asking is expecting me to say I have a fancy office downtown with a huge staff.


Every time I take a conference call in my gym clothes or I write a blog post with my feet up on the couch (like now), my heart wants to explode from the freedom I enjoy.

I’m coming up on my two year anniversary as an entrepreneur, and the anniversary is taking a toll on me. While two years is nothing compared to many entrepreneurs out there, it’s still 700+ days of:

  • emotional and mental trials
  • exhaustion
  • creative abandon
  • gut-wrenching anxiety
  • jump-in-the-air excitement

Sometimes, all within the same day.

In the past, I’ve shared how the choice to “do my own thing” has altered my identity (for both good and bad), but I’ve never sat down to question why.

This lifestyle — of wanting more, better, greater — sometimes hurts, and I want to know why, especially because many of you have experienced something similar.

Today, I want to deep dive into why it’s sometimes difficult to want what we want.

Let’s get to the bottom of this, shall we?

First of all, what do we want?

Every single one of us brings within us a unique set of wants and aspirations.

We’ve been taught since kindergarten that we’re all different and special, right? But what we haven’t been taught is that we are always different from our own selves — that is, we change and evolve over time. Our unique set of wants and aspirations does, too.

During my TEDxTalk in 2012, I spoke about how my interests have changed over the years. As a young girl, I wanted to be a teacher and a mom. In high school, I wanted to do something with computers. After college, I enjoyed marketing. Now, I rolled all of those desires into one business in what seems to be a wonderful full-circle (except for the bit about being a mom, which will come later, I’m sure.)

It’s all a continuous flow of change, growth, and experiences.

If you look at most people’s careers, you will notice the same trend:

Oprah Winfrey (who I’m obsessed with) started out on radio before moving to evening news and then onto day-time talk shows. Now, she owns her own television network and magazine. Her latest ventures include personal development shows like Lifeclass and Super Soul Sunday.
The team at 37Signals were technology consultants for years before they started working on their very popular project management tool, Basecamp. Now, they’re also best-selling authors.
Jay-Z started out as a rapper for years before he decided to venture into different industries as an entrepreneur. He’s tried his hand (and succeeded) at clothing, music production, sports, and more.

People in the technology world would call these “pivots,” but what we call them doesn’t matter. What matters is the openness to change.

Take your own life, for example. What twists and turns has your own career taken over the years? What interests have you followed down a rabbit hole?

What you want now is very different from what you may want in six months — and that’s okay.

That sounds so wonderful, right? It’s a picture painted full of opportunity and freedom! Why are we talking about any of this “hurting” when it’s all so great?

We get to change and transform when we feel like it.

We get to follow our desires as they pop up.

We get to do what we want when we want.


To a certain extent yes, but this is where things start getting difficult.

What’s difficult about aspiring to more?

We’re all about transitions, about transformations, about living our ideal life — but do you know what happens when we make each of those shifts?

Each shift opens us to incredible opportunity, but it closes off opportunity, too

In the words of Danielle LaPorte,

“Creativity always has an element of destruction to it.”

Here’s what I mean:

When I quit a corporate job to start my own business, I open and closed opportunity.
When I dismissed 2/3 of my team to up my freedom, I open and closed opportunity.
When I became more selective in the clients I work with, I open and closed opportunity.
When I started devoting my time to creating a tool for freelancers, I open and closed opportunity. (Announcement about this coming on Sunday! More info at the bottom of this post.)

In creating my dream life, I’ve had to destroy so many things. Some of them were good. And that hurts.

It hurts to let friends, projects, and opportunities go, even when you’re moving toward something you want more. I’m sure it wasn’t easy for Oprah, 37Signals and Jay-Z to make each shift, even though they were leaping onto something bigger and better each time. I’m sure it won’t be easy for you to make shifts, but that doesn’t mean you shouldn’t do it.

It’s not easy for Kermit the Frog to be green, but he’s got no other choice.

It’s not easy to want what I want, but I have no other choice — and neither do you.

No matter what you’re aspiring to, it may hurt. And I’m not sure the word is may. I really should say that it will hurt.


Is the hurt worth it?

This post may seem full of complaints, but it’s just full of the truth.

Every single move I make has pros and cons, and everything goes up and down: the friends I have, the money I make, the contentment I experience, the free time I enjoy.

Over the past two years, I’ve come to my husband in tears more times than I can count. The same goes for the amount of times I’ve come to him for a high-five.

The high’s are high and the low’s are low, so it boils down to this:

Is it worth it?

For me, there’s no question about it. I can’t help but want what I want, and I can’t help but keep experimenting. The thrill of designing a new app or writing a new blog post keeps me absolutely hooked, no more how rough the road gets.

The only way to get through the tough times is remembering why I’m aspiring to more in the first place.

Sure, entrepreneurship hurts sometimes. Sure, it’s gut-wrenching to open my email inbox from time to time. Sure, I hit a technical snag every few days. But there are a handful of things that get me through those moments:

  • Emails and comments from people who resonate with my writing (I love every single one of you more than you know!)
  • Feedback on my apps and designs that is positive or constructive
  • Spending time with the people who matter to me during the middle of a workday
  • Getting lost for hours in a tangle of words or wireframes

To me, those good things make the bad things 100% worthwhile. In the words of Ralph Waldo Emerson:

“I am a willow of the wilderness, loving the wind that bent me.”

Everything changes over time, and that’s okay. I’m just a loving product of those changes.

But enough about me and my experiences. I’d love to hear from YOU:

What kinds of shifts are you looking to make in your life? Have you ever suffered for shifting to something better? What is your biggest concern is making shifts in your life?

This is a topic that I receive a ton of emails about, so I hope we can all learn from each other’s experiences below in the comments. There’s so much for me to learn about, at least.

If we rally enough solutions or pieces of advice, I’ll write them up in my next post.

Wishing you awesomeness from Managua!

— Marcella