Am I Turning Speed Bumps into Roadblocks?

During an episode of my podcast, as my former cohost and I dug into some struggles he was running into getting his product to escape velocity, I said this phrase: “It sounds like you’re taking speed bumps and turning them into roadblocks.”

As a founder, you can choose to look at an obstacle as something that keeps you from moving forward (a roadblock) or as something that slows you down for a minute as you continue along your path (a speed bump).

As I look back on my experience building startups, I can see how my mindset around this has evolved over time. In the early days, everything seemed like an insurmountable roadblock, a company-ending event.

These days I force myself to view things as speed bumps. As I’ve made this seemingly simple mental shift, I’ve become more effective and less stressed.

Problems are inevitable when you are building a company. When they arise, if you find yourself using phrases like the following, your founder lens is viewing them as roadblocks:

• This is too big to fix.
• If this doesn’t work, the business is finished.
• I’m out of ideas. I can’t make this work.

Obviously there are situations where a problem is an actual roadblock. A roadblock is a business-ending situation where a platform is shutting down its API or you’re being sued out of existence. Although these things happen, they are much less common than speed bumps.

The tricky part about speed bumps is they masquerade as roadblocks. They do this by taking advantage of your lizard brain. The stress and uncertainty we experience as we build companies leave us vulnerable to believing things that simply aren’t true.

We often do this because our stress level is high and our minds don’t quite know how to handle it. When we’re in a constant fight-or-flight mode, most things feel like an existential threat. They feel business-ending.

I recall trying to land a major customer for Drip, and my inner voice was saying: If you don’t land this customer, the business is going to fail.

That statement was factually inaccurate. It would have been a disappointment if we didn’t land the customer, but every month several significant potential customers showed up in our inbox. We had options.

This was absolutely a speed bump, not a roadblock. But I let it become a roadblock in my mind, taking a toll on my happiness and productivity in the process.

In the early days of TinySeed, I spoke with a founder who decided not to accept our investment terms. My inner monologue was telling me: Our approach is too new, and people aren’t ready. It’s not going to work.

Yet here we are years later with batches of successful startups I couldn’t be more proud to work with. In retrospect I turned a minor rejection (a speed bump) into a mental roadblock that stuck with me for days.

Roadblocks put stress on your mind, on your body, and on your relationships. It’s no way to live, especially for folks who are building startups to improve our lives.

We don’t have to grow at all costs or answer to a board. We build startups with the handicap of not being able to raise buckets of funding. Not receiving funding means hard-earned freedom, and you shouldn’t squander it by letting your mind manufacture roadblocks where there are none.

At some point a couple years ago, I realized that all the stress and worry over my then 14 years building companies was not a good thing. When people ask what my biggest regret has been as a founder, it’s that I stressed too much about things that were going to work out. I made roadblocks out of speed bumps.

My process for solving problems has moved from stressing about everything that could go wrong to mapping out three or four possible options if things do go wrong. Often these options are not optimal, but none of them would be business-ending.

Typically they involve spending more money, investing more time, turning down a lucrative deal, or navigating a sticky situation. These are all things I’d prefer not to do, but none would ruin the company.

Making the mental shift from “everything will end” to “we’ll switch to plan B, C, or D” has been one of the biggest leaps in my own psychology. I’ve realized this over the past few years, but I heard it in full force in the podcast episode I mentioned at the start of this section.

I would not be overstating to say this has been a life-changing realization. My regret is that I didn’t discover it years ago.