The Founder’s Paradox: How to Know When to Change Course and When To Keep Going

I love the adventure of travel. I am always looking to see and learn something new about a place and the people who live there. Right now, I am writing this from Italy where I am vacationing with my family. Driving here has been an adventure itself. The streets are ancient — narrow, wildly winding, and punctuated by faded signage that confuses more than guides. There have been quite a few “Are we sure this is the right way?” conversations with my wife and kids.

Knowing when to change course and when to keep going is an essential skill for any traveler.

After all, sunny skies can turn to dark clouds quickly — leaving you caught out in a lightning storm. Just last summer, I got caught in a hailstorm at an alpine lake and had to take cover under a large rock overhang. We were backpacking in the Emigrant Wilderness in the Sierra Nevadas, up 9,200 feet. I go every year with friends and know the Sierras quite well and have been drenched before.

Entrepreneurs and company founders have also come to expect the unexpected. You know it might happen — you just do not know when. The only thing that matters is how you respond and which direction you head when it happens. This is what you signed up for.

Any big adventure worth the investment of your time and energy will have at least a few surprises along the way. And you need to know what you want to achieve in order to make the best decisions as those surprises happen.

These are not just words to me — knowing what is really important to you no matter what challenges you face is essential.

I write a lot about strategy. Often, I write about goals and initiatives as your “north star.” This is because strategy represents the best insight you have right now into what you think will create the most value in the future. But there are times when a company has to make strategic shifts — rethinking your product, seeking different types of customers, or exploring a radically new go-to-market approach.

This is why the decision to change course needs to be taken so seriously — your choices matter. You need to think deeply about why you want to take a new path and the implications of changing direction. Is what you are experiencing temporary or something fundamental, even structural? Are you thinking rationally or emotionally? Has your north star moved and you need to move with it?

Setting strategy is among the most important work a founder does — surpassed only by when you have to change it.

It is common to want to pursue what is new — so you need to challenge the reason why you are ready to stop what you are currently doing. When that feeling does strike and does not go away for a few days, I suggest you use the following guide to determine whether your intuition is right and your current direction is wrong:

Your original assumptions were wrong

You are a company founder. And while that requires vision and insight, you are not a seer of all and predictor of the future. There will be times when you realize that your original assumptions were simply wrong. And now you know a new truth. Embrace it and move forward.

You are not selling

Both figuratively and literally, your customers are not buying what you are selling. They are telling you that they do not believe in what you are selling. A business requires that someone wants to pay for the product or service that you deliver. This may sound shocking in today’s world of never-turn-a-profit, billion-dollar startups. But if no one will exchange meaningful value for what you create, then you are not operating a sustainable business.

You keep missing goals

You set those goals based on what you understood at the time. But doing the same thing and failing over and over means something is not right. It is time to try something new or adjust the goals you are setting. Take a hard look at what you find. (Just beware because it may be that you are making progress but your goals were simply unrealistic. This is particularly common for venture-funded companies that made overly aggressive promises to investors prior to raising money.)

You were talked into it

Founders are not immune to this. And it is not always ill-intentioned — plenty of company leaders have championed ideas from teammates or advisors. It is required if you want to continuously innovate because not all ideas can come from you. But if you went with another idea and it failed, you cannot live with that as an excuse. Take responsibility for your current strategy. Be accountable for its failure. And change.

Your team does not believe

There will always be folks who have doubts. Just as there will always be folks who vociferously encourage every decision you make. I am not talking about either of those. When your team is telling you in just about every way that you need to change, do something different, or that the road ahead is not one that they want to follow you down — listen.

Not every faded Italian road sign is worth following. And not every dark cloud holds a lightning and hail storm.

The key is to honor reality and have the self-awareness to clearly see what really requires your attention. And what is simply a challenge but not one worth changing direction over. The strategic decisions you make are part of the great adventure of being a founder. Honor the responsibility and go boldly.

Read more of The Founder’s Paradox.