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How Entrepreneurs Learn to Build (and Rebuild) Their Company Roadmap

If I’m talking startup roadmap I’m contractually obligated to use this metaphor.

After building a dozen startups, I can tell you that the hardest thing about being an entrepreneur is that it’s too easy to get caught up in what should be rather than what will be.

It’s a tricky problem. As entrepreneurs, we’re driven, ambitious, and headstrong. When we want to accomplish something, we take stock of where we are (Point A), we sketch out where we need to be (Point B), and then we map a straight-line path from one to the other.

We live off that map. We keep it close by, we detail it. It’s the first thing we look at when we start our day and the last thing we review at the end of the day.

And to tell you the dirty truth, we really like doing this. It’s a guilty pleasure. We’re nerds for it.

The First Big Miss

But then we take our first big growth step — closing that first sale, launching the MVP of our product, whatever it may be— and when the data starts coming in, we realize we’ve wound up slightly to the left or to the right of plan, maybe even back a step. Then, thanks to equal doses of human nature and ego, we get rattled, and we immediately start throwing too many resources at righting the ship.

This manifests itself a number of different ways. We get concerned, worried, even angry. We obsess on why the data missed our targets. We may lay blame, internally at ourselves, externally at a lazy or uneducated market — maybe at a machine stacked against the “little guy.” We might start fine-tooth-combing every part of our process, looking for that one small flaw that’s screwing everything up.

We can do this for a while. It’s natural to get all tweaked when the chips don’t fall where we want them to fall.

But do this too often or for too long, and we’ll wind up with a load of regret.

I’ll explain.

The Roadmap Paralysis Trap

This phenomenon, what I call roadmap paralysis, is not unique to entrepreneurs and startups, it’s actually pretty common.

Pick a goal, and not a stupid one, but something that encapsulates one or more things you want out of your life. Now visualize it. The more likely you are to be able to visualize that goal, the more susceptible you are to the roadmap paralysis trap, because that goal, that dream, is right there in front of you. You can freaking taste it.

Figuring out what you want is half the battle, in startup and in life.

Most entrepreneurs become entrepreneurs because they can visualize a goal, but instead of setting personal or professional goals, they’re trying to solve problems bigger than their own. They see the problem, they have the solution, and they’re convinced that their solution can be viable, effective, and profitable. So they get to work and charge towards that solution with all the resources at their disposal.

The Solution is The Goal

The singular true goal for an entrepreneur isn’t a valuation or a revenue number or a percentage of market share. In fact, if there’s a number at all, it’s a percentage reduction in the amount of problem they’re trying to solve.

The big mistake we entrepreneurs make when we build the roadmap is we use these numbers as markers on the way to the one true goal. And they’re mostly meaningless. Especially at the beginning.

A Sideways Death Spiral

So then we take more steps and more steps. Life doesn’t stop, there’s no timeout to analyze the plan and readjust, so it’s all done on the fly. And as we get further and further off the path and more and more desperate that things just aren’t going our way, we’ll done one of two things.

One: We’ll quit. Maybe not shut everything down and walk out the door kind of quit, but mentally, we’ll pack it in, and accept our fate and play out the string. We’ll look at our goal and we’ll look at our lack of progress on this beautiful straight and narrow path we’ve built, and we’ll decide that where we are is just fine. It’s OK.

Two: We’ll pivot, but for the wrong reasons. We’ll make grand, sweeping changes to the product and the organization to push the whole thing to the side like a car stuck in mud until we get back to that beautiful path. We’ll waste a lot of time and money trying to prove we were right in the first place.

The Goal Didn’t Change

The thing is, the goal didn’t change. It’s just that the path was never the right path in the first place.

We’re conditioned to believe that if we’re not getting to where we want to be, it’s due to a combination of internal factors (we’re just not good enough) and external factors (the whole world is against us) combining to derail us.

The truth is usually that the path we drew to the single true goal was never going to be the single true path.

Because there is no single true path.

Regrets? I’ve Had a Few

I said the word “regret” near the beginning of this post and I wanted to let it sit for a while before I explained how that regret comes into play.

We’re not going to regret the idea, because if the idea sucked, we never would have gotten the motivation to execute on it in the first place. We’re not going to regret the time and effort, because if we’re truly ambitious and driven, we’re not going to be satisfied with the same markers of success everyone else is using.

We’re going to regret the fact that we spent so much time looking at the gap between where we are and where we think we’re supposed to be that we didn’t realize we were already halfway there.

We just needed to redraw the path.

And enjoy the journey.

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