I’ve been asked this 10,000 times and my answer hasn’t changed much over the years (and it’s honestly not that unique or special either as you’ve probably heard it before yourself).

But after some of the very large changes that have happened recently I’m forced to confront that question for myself even though I’ve counseled many before on the exact same thing. Of course, it’s always different being in the “hot seat” instead of someone asking you to put them there!

I’ve often suggested that people do 1 of 2 things; sometimes they are the same thing and sometimes they are not:

1. Zero Constraints

Sometimes I just ask the following question:

What would you do if you have absolutely zero constraints?

Most people then ask what I mean by “constraints” and I just ask them what they think I mean by “constraints” – I do this because the answer is different for every person and constraints for some people aren’t actually constraints for others.

Common themes arise like financial constraints, social pressures/expectations (from colleagues, friends, parents), and a few others. “Timing” perhaps is a often-cited constraint.

I tell them to go pursue it anyways. I have a number of reasons why:

  • We honestly have no idea if the constraints that we believe will be constraints are actually real constraints the moment we start. Things can change so rapidly that an entirely new environment can unfold literally before your eyes if you gather the courage to take the first step.
  • Help comes in all shapes and sizes and there are more people willing and ready to help you than you might imagine. Pursuing something challenging doesn’t require that you do it alone.
  • What you believe you are pursuing will most likely change and evolve the moment you take that first step. Our minds trick us to believe that what we have crafted in our tiny pea brains is going to be fully represented in reality at the end of the journey. That never happens.
  • Luck, circumstance, serendipity, and all of those things are such a serious part of doing anything worth pursuing that you can’t account for it nor can you discount it for a moment. But in our hearts we don’t allow ourselves to “plan” for the random because that would be foolhardy or too simple-minded. Too bad as these elements are the things that make it the most fun.

In the end I think that life is too short to not at least give it a try – I don’t want to live a mediocre life where I’m always giving into the resistance. So just go for it! I mean, you can always jump back into that comfortable spot you’re sitting in right now – you at least know how to get to there.

2. In Flight

Sometimes the “next” thing that you really need to be doing is already there staring you in the face – we just don’t see it as an opportunity that can grow and scale into something much bigger.

For example, if I were to answer this question myself the solution is quite clear: I’ve been working for nearly a full year on a small iOS application, Pressgram, that has scaled to become something that has a scary amount of potential.

I could honestly start something new and try to keep the app (and the growing movement of passionate believers) in a box and silo’d as a project in my own mind and heart but what’s the use? What’s the point of not giving it a full go?

The problem is that you and I are great at self-deception and we can come up with 1,001 excuses as to why we shouldn’t pursue it – you and I just need to sit down and fill in the blanks. I’ll list out a few of them that I’ve created for myself:

  • The app doesn’t make any money. I should go do something that makes money.
  • I’ve never build such a large iOS app before and so my experience is limited and is not enough to make sense moving forward full time.
  • I’ve never built a business or organization around a piece of mobile technology. Perhaps I should wait until I have more knowledge, experience, or counsel.
  • I may have to raise a round of venture capital to keep the application and community afloat. What if no one wants to fund it?
  • I have a small group of passionate believers but what if they are the only ones who will ever really like it? I should go do something that guarantees a more mass appeal and market.
  • I don’t have any cofounders or partners yet. I should wait until I find someone that will come in and help share the load.
  • I should play it safe and go get a real job while continuing to build Pressgram on the side so at least I can feed my family and pay my mortgage.
  • Etc…
  • Etc…
  • Etc…

These can be seen as very legitimate in many ways and for you your list may be a lot bigger and much more comprehensive. But on the same “What If…” coin that you toss around in your mind is a very similar question:

What if I do go all-in and it blows my expectations out of the water completely?

It’s just as possible as a few of the other scenarios to be honest. And if I have doubts I just have to revisit the above list of “constraints” to set my mind right.

When you’re faced with the question of what you should do next sometimes the answer is looking straight at you in the mirror, begging you to jump in with both feet. You don’t have to start anything new as you’ve already got your new thing that just needs a new (and greater) amount of attention.

Here’s to the crazy ones.