Nate Green

The Dark Side of Ambition (Plus, 11 questions to ask before you start anything.)

Nate and Jason in a gang
The two illest, most dangerous 14 year olds in Montana.

When we were 14, Jason and I started a gang.

We did all the typical gang-related stuff you’d expect from two white, middle-class kids from a small ski-resort town in Montana:

We stole candy bars from the grocery store, made napalm out of gasoline and styrofoam in our driveways, and terrorized small dogs and old ladies with our skateboards.

Sadly, we disbanded after only a week, right after Jason stuck a rolled-up Limp Bizkit poster down his pants and got caught as he attempted to walk out of the store like a goddamn pirate with a peg-leg.


Even though our gang didn’t last long, our ambition to start things and be a part of something stuck around.

We were ambitious kids who took action on our ideas. And so we grew into ambitious adults who continued to take action on our ideas.

Even if some of those ideas were absolutely terrible.

A Very Short List of Very Terrible Business Ideas We Tried

Underpants gnomes

1. Vagabrew: A beer blog where we’d travel to different breweries around the country and write about them. Our business plan followed the Underpants Gnomes formula:

Step 1: Drink beer, take road trips, and write about breweries.

Step 2: ???

Step 3: Profit!

2. A children’s book about robots. Each robot was made in a factory, but they were all missing a crucial piece that made them feel empty inside: They were missing….a heart! (We sat for 5 hours writing the entire outline before realizing how incredibly stupid it was. Personally, I blame the bottle of bourbon we drank while we wrote.)

3. Humblecock: A clothing company we started because, well, why the hell not? We put a giant rooster on t-shirts and ran it for two years before we finally admitted we had no clue what we were doing. (Five years after selling it, we realized we forgot to pay taxes on three months’ worth of income. The IRS sent us a bill for $20,000 in penalties. Oops!)

And that’s just the stuff off the top of my head; it doesn’t count all the dozens (maybe hundreds) of little ideas that sounded cool at the time, but that quickly transitioned to stressful wastes of energy that made me hate my life.

Why Most People Will Fail to Reach Their Full Potential

A couple weeks ago I talked about why most people will fail to reach their full potential: They have an idea of what they’d like to do, but they’re too afraid to start. OR they overanalyze every single option and end up staying stuck in the same position.  (My suggestion for them: run a small test.)

Well, there’s a flipside to this: While some people are too afraid to start anything, lots of other people will fail to reach their potential because they’ll try to start everything.

They’ll try to take action on too many ideas.

They’ll be like young Jason and me, writing books about robots and owing the government 20 G’s in back-taxes.

Mike HC
“Wait…we owe how much?”

It took me years of practice (and failure) to figure out the crucial difference between ideas that sound good…and ideas that are actually good. 

Not a good idea:

Taking action on any idea that sounds cool or feels like something you should do—especially out of a sense of urgency, panic, or fear of missing out.


  • Quitting your job and cashing out your retirement to open a new business
  • Going back to school and spending tens of thousands of dollars on classes because you don’t know what else to do
  • Launching a product that looks and sounds exactly like everyone else’s product
  • Starting a clothing company with the word “cock” in it

A good idea:

Taking action on an idea that allows you to use or build a valuable skill, helps other people, and aligns with the kind of lifestyle you actually want to live.


  • Making the transition from valuable employee (with a 9-5 schedule) to valuable consultant (with more freedom over your schedule)
  • Finding ways to be more effective and productive in your work so you can finish faster and spend more time with your family
  • Starting a blog about something you’re deeply interested in, sharing your thoughts and experiences, and building trust with your readers as you figure out a way to help them solve a specific problem.

This is the difference between blind ambition (ambition without a clear purpose or direction) and focused ambition.

The Dark Side of Ambition

If I’ve learned anything about my readers over the past 9+ years it’s this: You’re ambitious as hell.

In fact, your ambition probably sets you apart from the rest of your friends and family. I mean, who else reads self-development blogs, listens to podcasts, and buys books with names like The 4-Hour Work Week or The Hero Handbook?

Face it: You’re weird. And I’m right there with you.

Our ambition is an asset…until it’s a burden.

At its most trivial, our blind ambition can be a source of constant frustration as we make false-start after false-start and struggle to figure out what to do next. After a while, our lives can seem like a series of “almost made-its.”

But at its worst, blind ambition can destroy our self-confidence and our relationships with the people around us.

Blind ambition is how we end up working on weekends, neglecting our health or family, or overwhelming ourselves with too many ideas. It’s how we end up taking on too many commitments, shortchanging other areas of our lives, or going into debt.

When we’re blind, we struggle to set boundaries, fail to finish what we start, and become ridiculously stressed out in the process. We end up, as author Greg Mckewon says, making a millimeter of progress in a million different directions.

Blind ambition
Blind ambition leads to a millimeter of progress in a million directions.

But focused ambition is a beautiful thing.

It’s life-changing and inspiring. It makes us better…and it makes the people around us better, too. Focused ambition moves us forward. 

Screen Shot 2016-03-21 at 10.58.12 AM
Focused ambition moves us forward.

How To Focus Your Ambition: 11 Questions To Answer Before You Start Anything

A few years ago, Jason and I wised up: We started applying criteria to our decision-making.

We wanted to be confident that every idea we decided to pursue would take us in the right direction—even if it eventually didn’t work out. (Not all good ideas are successful in the long run. Actually, very few are.)

Since then we’ve developed a more detailed personal criteria based on 1) our most valuable skills 2) the lifestyle traits we want to protect and build.

(This is something I’ll talk in more detail about soon.)

But we both started with this: A series of questions we’d ask ourselves before we decided to change jobs, take on any new project, or chase down any new idea.

Questions like…

  1. What exactly do I want to do?
  2. What’s the point (what am I trying to accomplish)?
  3. Why is that important?
  4. Does this match any of my current skills? (Or will it allow me to build a new skill?)
  5. How, specifically, does this help other people (my company, customers, family, etc.)?
  6. How long will I try this before I move on to something else?
  7. What does “done” or “success” look like, anyway?
  8. Is this really how I want to spend my time?
  9. Can I get the same result in a way that’s easier or less time-intensive?
  10. What will I have to give up if I decide to take this on?
  11. What simple test can I run to get started and see if I’m on the right track?

Answering these questions takes time (sometimes hours, days, or even weeks) and requires critical hurt-your-brain-type thinking.

Of course, not everyone is willing to spend the time or energy to think this stuff through…but they’re the same people who are going to fail time after time (unless they get lucky).

Better Criteria = Better Decisions

The simple act of taking the time to answer these questions and work through the implications of each allowed Jason and I the opportunity to gain perspective on what we were really trying to accomplish and why.

By applying a simple criteria, we learned how to evaluate sticking points and opportunities in both our careers and our lives. We learned when to stay and when to move.

Most importantly, we learned how to make better decisions and pursue the right ideas—the kind of ideas that bring us closer to becoming the people we want to be, helping the people we want to help, and living the way we want to live.

Do this next:

It’s super-basic but incredibly effective: The next time you feel like it’s time to change something about your life—or the next time you have an idea for a project or business—ask yourself The 11 Questions. See if they help you identify your next step.