Dear Founders and CEO’s (and anyone trying to grow in their careers, or raise a teenager): I have some bad news for you, and some good news. It never gets any easier.

How is that both the bad news and the good news? Bear with me for a few minutes.

Last year, I was going through a particularly stressful time with SureSwift. I was bouncing between feeling totally euphoric after a win and then feeling pissed or depressed when I’d hit a new obstacle.

On a long, quiet drive a phrase popped into my head. I have no idea where it came from, but it’s stuck with me many months later.

“It will never get any easier.”

As companies grow, they get more complex. That means it gets harder, not easier. Even having an amazing team doesn’t solve every problem. (But it sure does help. We’re hiring for that amazing team, btw.)

And bigger company = bigger problems. A friend once said the same thing to me about parenting. “Small kids, small problems…big kids, big problems.” Hence my earlier shout out to those of you with teenagers!

Based on my own experience — and my conversations with bootstrapped Founders, advisors, investors, and hundreds of successful entrepreneurs in other industries — there’s also no finish line in business until you sell or retire. (And really, if you think about it, those are both probably starting lines.)

So that’s the bad news. It never gets easier, and there’s no finish line. By now some of you are thinking, “Thanks, Kevin. This post really sucks.”

So let’s get to the good news part.

The good news is that if we let go of the idea that things will get easier… it stops being so hard.

Because you’re not looking up the mountain you’re climbing anymore thinking, “If only.”

“If only we could get to the next level.”
“If only we could hire the right key person.”
“If only we could land that big customer.”
“If only we could secure the next round of investment.”

Those are all “If only’s” I had in my head last year when I was stressed out. Yours might be the same, or they might be different. The point is that there’s a fundamental flaw in this line of thinking.

And that flaw is this: As soon as you reach a peak — or check off one of those “if only’s” — you’ll look up and see the next mountaintop and that next peak is likely higher and steeper than the one you just climbed. But you’re seeing these new peaks because you summited the earlier ones. Climb the next one, and you’ll see a whole new set. It’s just the cycle of running a business.

Knowing that, it’s really helpful to reframe your thinking. Because if you stop expecting things to be easy, you won’t be disappointed when they’re hard. And when you expect things to get harder as you grow, they actually feel less hard because you’ve become that much more resilient and capable of handling it. It’s like mental Jujitsu.

I wanted to write this post because while the bootstrapped SaaS community is an especially awesome and supportive group of entrepreneurs, I think many Founders feel like they need to put up a front that everything is going great 100% of the time. I’m sure we can all name at least 5 Twitter accounts that propel this myth.

And while I think we all probably call “bull sh*t” to ourselves when we see that happening, I think it’s worth saying out loud: Running a business is hard. The time to start worrying might actually be if it’s starting to feel too easy.

What do you think? What’s punching you in the face right now in your business? What helps you get through it? Let’s keep the conversation going on Twitter.

Join the Founder’s Squad

Founder stories, advice and case studies.

You have successfully subscribed!