I co-host a podcast that focuses on bootstrapping software startups. Last week as my co-host and I dug into some struggles he’s running into getting his product to escape velocity, I started saying a phrase I hadn’t used before:
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 at my experience building startups I can see how my own thinking 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, the more effective and less stressed I’ve become.
Roadblocks
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. This is a business-ending situation where a platform is shutting down their API or you’re being sued out of existence. While these things happen, they are much, much less common than speed bumps.
Speed bumps
The tricky part about speed bumps is they masquerade as roadblocks. They do this by taking advantage of your founder brain. The level of stress and uncertainty that we experience as we’re building companies leaves us vulnerable to believing things that simply aren’t true.
Often, we do this because the level of stress we’re experiencing is high and our minds don’t quite know how to handle it. When we’re in this constant fight or flight mode, most things feel like an existential threat.
“Business-ending”
I recall working on landing a large customer for Drip, and my inner voice was saying:
If you don’t land this customer, the business is going to fail.
That statement is factually inaccurate. It would be a disappointment if we didn’t land the customer. But every month several large 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 6 months later with a full batch of 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 multiple days.
Unnecessary Stress
Roadblocks put stress on your mind. Stress on your body. Stress on your relationships. It’s no way to live, especially for folks who are building startups to improve our lives rather than re-arranging our lives around our companies.
We don’t have to grow at all costs or answer to a board. We do it with the handicap of not being able to raise buckets of funding. It’s hard-earned freedom, and it’s something you shouldn’t squander by letting your mind manufacture roadblocks where there are none.
At some point a couple years ago I realized that all the stress and all the worry over the 14 years of building companies was not a good thing. When people ask what my biggest regret has been as a founder, it’s typically that I stressed too much about things that were going to work out. I made roadblocks out of speed bumps.
Optionality
My process for solving problems has moved from stressing about everything that could go wrong, to mapping out 3 or 4 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, 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 heard it in full force in the podcast episode I mentioned at the start of this essay.
I would not be overstating to say this has been a life-changing realization for me. My regret is that I wish I’d discovered this years ago.
