Your Dream is only 7 Years Away

I went to a startup conference a few weeks ago.

I know what you’re thinking – my life must be super-interesting if I’m attending something so riveting as a startup conference.

Just shut up and listen, ok?

The conference itself was…it was fine. Truth is, many of the entrepreneurs’ stories left me feeling discouraged. But that’s actually a good thing because it helped me realize that running a business–or pursuing a dream–involves a compensation plan that runs much longer and goes much deeper than a simple money-for-time arrangement.

For a handful of the speakers, their brands are about 4 years old, and they still aren’t really making any money yet.

And that’s not usually the story you want to believe. You want to believe that you start a company and it starts making money in the first month or two, and if it’s really a success, you’re living richly within a year.

But that wasn’t the case for this group. This group had success, but their success tied them even more tightly to their work, and to needing more funding, and to stretching every penny as far as they could.

But in listening to the founders that were able to hold out a little longer, the story changes significantly.

Of those that held out for another year or three, things changed for them. All of the sudden, money started flowing, business started solidifying, and the dream started to feel less like a nightmare.

Maybe it’s magic or voodoo, or theoretical physics, but in that fifth year growing brands that continue to muddle through the uncertainty start to see a shift in how easy it is to do the things that used to be hard. They’ll find bigger, better partners. Their operations will smooth out (a little). Their margins will finally be closer to where they should be and their growth will either slow to a manageable rate, or they’ll be better positioned to handle the growth.

Along with all that, they’ll finally get better at hiring good people. They’ll learn how to hire people that actually get shit done. They’ll learn how to delegate the inefficient tasks and how to bring real value to the strategic initiatives that will accelerate their success.

But it takes time.

I don’t know how they afford to live in Park City. I don’t know how they afford to have a warehouse and employees, but they make it work.

And eventually, it seems to pay off.

With almost as much certainty as you can get in this life.

And it’s not just entrepreneurship, it’s any vocation. And sometimes it can take more than 7 years, sometimes it takes 10 or 15, depending on how competitive the area of focus is.

  But usually it’s 5-7 years.

Remember that Bible story of Jacob and how he worked for Rachel’s dad for 7 years (and her dad screwed him and gave him the ugly sister, so he worked for another 7 years)? Point is, this 7 year mark has been around for a long time.

The cycle goes like this:


It takes about 6 months to get the hang of something. Three of those months are spent figuring out what the hell you’re supposed to do to begin with, and then the next 3 are spent actually setting things in motion. And then, after that, you’re able to have a series of victories and defeats until you finally feel like you’re getting the hang of it.

Which usually happens around…


And once you’ve hit 3 years, there will be a crossroads – you will come face-to-face with disillusionment. Sometimes it happens before, sometimes a little later, but eventually everything you liked about the industry will seem sullied.

             The magic will be gone.

      You’ll not be able to ignore the politics.

You’ll see behind the curtain, and it will seem inauthentic and contrived and fake.

And you don’t have to stay. This is an ok time to leave the field if it no longer holds you. You gave it a shot and you got a real feel for what the industry held for you.

    Just know that almost any career path will present this challenge.

And if you do push through, you’ll realize that there are two paths that can be taken from here on out: the contrived path and the authentic path.

Most people take the contrived path because that’s all they know. They think that’s the way it’s supposed to be done. And so they use manipulation and pretense and tactics and stratagems to stay ahead of the game. And what they don’t realize is that it doesn’t have to be a game. They don’t even have to compete.

The authentic path brings you back to basics. It is one of sincerity and it becomes more about the work than your reputation.

     The authentic path isn’t about networking.
It isn’t about finding new business or new opportunities.

It’s about doing great work.

And getting your work in front of the people that can appreciate it.

It is about honing your craft and having coaches and mentors and challenges and staying vulnerable and feeling uncomfortable. And it’s sort of what these entrepreneurs kept talking about; They kept saying how they measure their success differently: Now they measure their success by being able to have their own company and work together and choose who they work with.

The contrived path seeks safety.

The authentic path seeks courage.

5 – 7 YEARS

Once you’ve crawled down your chosen path for a couple years, your reputation can’t help but be attached to you. If you’ve worked hard and not taken the easy route, you’re probably starting to make good money. And you’re starting to find other promising characters in other fields. The big-picture things become clearer.
You understand what expertise means and how it’s developed.
And it doesn’t matter if you’re performing for an audience or doing creative services for a client, the whole “game” of it all – which is really just getting the audience to appreciate and talk about your work – happens because of the quality and uniqueness of what you do. It isn’t about marketing. It isn’t about strategy.
But it doesn’t happen in a vacuum, either. You do put yourself out there. You do promote. You do talk. You reach out. You collaborate with other professionals. But you do it to grow. You do it to connect. You do it to create. It’s not networking – it’s connection.

And eventually you realize that success has more to do with blurring the lines between work and deep satisfaction. You realize your career means something to you not because of the money it brings in, but because of all the creative brain children you’re able to birth and develop and watch go-forward and contribute to the world. It becomes a lot more about having a purpose and leaving something meaningful and valuable behind when your short stay on this planet comes to an end.