When Facing the Challenge of Uncertainty…

If one knew ahead of time all the challenges they would face in the foreseeable future, they wouldn’t be all that challenging. In fact, knowing what you’re up against would be a huge advantage. Especially in the world of startups.


There are so many challenges that I have yet to face, and while I’d like to think that I’ve already had my fair share, I would be naïve to truly believe this; the worst are definitely yet to come.

There are always myriad articles of advice, personal accounts and interviews to read up on. And with each one, hopefully a bit of knowledge is gained along the way. Each bit of knowledge eventually compounds into an arsenal of mental notes kept in mind as you face your challenges, in hopes that this arsenal will help you better overcome your difficulties. Some challenges will come and go as you defeat them, but one of the biggest that will always stick around is dealing with uncertainty.

The uncertainty of diving head first into something whose foundation isn’t solid, nor is its existence guaranteed to last, might be more frightening to those who care about you than it is to yourself. Let me explain.

To those beginning a startup, or anything that doesn’t guarantee or highly increase your chances of success for that matter, the thought of “failing” (I use the term loosely) is virtually non-existent. Why?

If you go into something uncertain if you can succeed, you’ve already failed.

Some will admire it. They’ll admire your courage to dive into something that doesn’t promise success (even though nothing does) and work nonstop as though it’s just outside your reach. Some want to see you succeed. And others, they just don’t want to see you fail. The first people like this that come to mind are family; The ones who support you the most and will stick around much longer than your closest friends. Sometimes, them not wanting to see you fail is accompanied by wanting to see you choose a path that has attributes like job security and income stability, among others. All things that don’t exist in the world of startups.

This was the unexpected challenge.

How do you convince the ones who care about you the most that this is what you want to do?

That innovation, disruption and creation are what you want your path attributable to?

How do you convince those, who you owe the most to helping you get to where you are today, that you want to create something for the world to use, and change the way things currently are, instead of spending your life hopping from corporation to corporation answering to someone above you for a salary, no matter how many figures?

No article I’ve ever read or speaker I’ve listened to prepared me with how to deal with this challenge.

On one hand it is totally understandable, similar to the parental instinct to always keep your kids safe. It’s something that will never wither or fade away for as long as you’re surrounded by them. Sometimes their desire to ensure your safety is greater then their desire to see you succeed. It doesn’t mean they don’t want to see you succeed, they just want it to happen in a way that is more sound.

So how do you give both sides what they want? How do you continue with what you believe you’re cut out to do while providing at least some sense of reassurance that even the worst case scenario for your business would still yield something positive? Anyone who sees potential in their startup or risk-filled endeavor wouldn’t be able to drop their plans without feeling an overwhelming mountain of regrets and what-ifs.

The answer I’ve come up with:

You continue exactly what you’re doing and dont look back. At the same time, you treat it as a learning experience, as something that no matter what happens, glamorous success or brutal failure, that you will come out of this having gained experience that will help you be safe in your next endeavor. You’ll learn from whatever mistakes you’ve already made and ones you’ll make in the future. Because in the end, that’s what those closest to you really want. Success comes in many, many forms, and you simply cannot blame those who care the most for your future for wanting success to come as safely and securely as possible. It’s natural.

It’s just part of the ride.
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