Let's Define Success By What We Don't Have To Do Anymore

“Why do we measure startup success by money? Is it the money we're truly talking about or the freedoms that money buys? If it's freedom, then how much of that freedom comes from money, and how much of it comes down to choice? Is any of it available to us right now?"

April 22nd, 2020   |    By: Wil Schroter

What if we defined success by what we DON'T have to do anymore?

What if we didn't have to work with people we don't like? What if we never had to miss dinner with our kids? What if we never had to think twice about taking a vacation?

Does this sound like startup Shangri-la? I thought so, too, until 8 years ago. I decided to build Startups.com based on everything I never wanted to do again.

It fundamentally changed my life.

The List of "No" is Life Changing

It turns out that making a list of things we don't want to ever do is actually much easier than a list of things we are trying to accomplish.

That's because saying "no" is more immediate. We can say, "I'll take more vacations when I'm really rich" (the "someday" paradox), or we can say, "No, I'm not going to work another hour until I get a vacation!" (Bam, I'm on vacay!)

Once we start applying "no" to all the stuff we really dread, it's shocking how incredibly powerful this can be. I said "no" to missing time with my family (we all stop working at 6 PM sharp). I said "no" to having to commute to work every day (now 200+ people work remotely). I said "no" to answering to anyone (we bootstrapped, not hard to figure out why).

Saying "No" is Freedom

For a long time I don't think I realized I could say no. I was so focused on what I was building toward - my amorphous vision of future freedoms — it didn't occur to me that my freedom was right in front of me. More importantly, I didn't realize that "no" was what led to freedom.

I kept thinking of freedom simply as something I had to run toward, not something I had to consciously avoid to get it.

Sticking to Commitments is the Hard Part

It's easy to make these commitments — it's really hard to stand behind them. That moment when some obnoxious investor is dangling a check that feels like it could change the trajectory of our business — do we say, "no?” Because that's exactly the moment that all of this matters.

We hit so many roadblocks on the path of building Startups.com that challenged our commitments, and many of them slowed us down or created more anxiety.

But the payoff — never having to do shit we don't want to do — is worth its weight in gold.

In Case You Missed It

How Do I Design My Startup Around My Life? There’s very little preventing us from designing our startups around our life goals. It starts with us being very clear about what we want to achieve and then taking clear, small steps toward those outcomes.

7 Habits Of Highly Successful Entrepreneurs From ice cream powerhouses to e-commerce pros, here are some traits from great founders that I’ve observed and tried to emulate throughout my 20-year career as an entrepreneur.

How Much Should I Be Working? (podcast) While there's truth to the assumption that more hours equal more growth, we'll explore how it benefits to think quality and not quantity when it comes to your weekly punch card.

About the Author

Wil Schroter

Wil Schroter is the Founder + CEO @ Startups.com, a startup platform that includes BizplanClarity, Fundable, Launchrock, and Zirtual. He started his first company at age 19 which grew to over $700 million in billings within 5 years (despite his involvement). After that he launched 8 more companies, the last 3 venture backed, to refine his learning of what not to do. He's a seasoned expert at starting companies and a total amateur at everything else.

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