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Becoming an Entrepreneur at 40 - A Hero's Journey, Part III

Stefan Loble

Making our way through Utah.


For the past few months, I’ve been writing a series about the “Hero's Journey.” Originally an observation by Joseph Campbell on how there’s a pattern to all great stories, my experience is that entrepreneurship is the same. Only that the story is ours.

Let’s imagine you’re the hero:

In Part I, you hear the call to adventure. Often to do something great, sometimes to escape a situation you hate… Like a job etc. Typically, it’s a little of both. For a while, you resist the call, until it wears you down, and ultimately you decide to dive in.

In Part II you cross the threshold, gathering resources to turn talk into action, and set out into the world to pursue your goal.

That’s good. You’re on your way. But Part III is harder...

Think of all the great stories you know about journeys... And imagine, what would they be if they were easy? If at some point, the going didn’t get tough, they wouldn’t be very interesting. And like all great stories, if you’re taking on something big, I bet a real trial is ahead for you too.

The Road of Trials: Here be dragons.

Here’s the thing about the road of trials — we’re talking about a real fight. Something big enough that your whole health, or company, or financial security may hang in the balance.

You may be thinking, “Come on, is it really that big?”

Let’s say you’re starting a company — maybe as an entrepreneur over 40, at a point in life when your lifestyle and obligations have become entrenched. Being successful will require real sacrifice, and a complete set of business skills.

Whether you realize it or not, businesses compete across the scope of their tasks — from building impressive products to hiring the right people. And as no one is an expert at everything, the bigger the challenge, the faster your weaknesses will become apparent.

And that is where the dragon will strike. Your job will be to battle threats in areas that aren’t your personal strengths. Whether it’s marketing, or managing a team, or negotiating with vendors, your weaknesses are where the challenges will be greatest. After all, the dragons that attacked your strong side are already dead.

Ugh. This looks like a big deal. And it is. If you could see how hard the Road of Trials would be before setting off, you might never leave the safety of home.

But if you’re an entrepreneur, or an adventurer, you see possibility where others see roadblocks. And you’re probably prone to ignoring just enough of reality to have the courage to take on something great.

The Key:

The key to your survival during hard times is a combination of being strategic in how you solve problems and taking care of yourself so you can stay in the game. A few ideas:

  • Find a peer. Entrepreneurship can be unbelievably lonely. In the face of real pressure, it can feel like there’s no one — not your friends, nor your family, nor your team — who has walked a mile in your shoes. It will be stressful for your support group to even talk to you about your challenge. My suggestion is to find someone who has been there. Some of my best support comes from other entrepreneurs — even competitors — who are living the same life I am. I’ve found that deep down, with just few words, they already understand. 
  • Operate at the right pace. Honestly, how many of your prior big ideas have you completed on time? You may have muscled some things over the finish line in the past, but a project as big as a company or changing careers will be your biggest one yet. I suggest gathering resources for your plan considering it may take longer than you expect. And before you start, think about who you are and how you ran other projects (organized but slow, versus fast and chaotic) because the same patterns will surface here.
  • Take care of yourself. Chances are better than not that you’ll sacrifice more of yourself in the form of health, finances, relationships than you probably should in an effort to keep your quest alive. It’s not uncommon to push yourself a little too far. In fact, entrepreneurship is notorious for causing depression, but it’s seldom talked about because no one wants to admit they aren’t up to the task. So make sure you exercise, meditate, paint… whatever it is that keeps your feet on the ground.

    We know we’re supposed to believe that good stuff will make us more productive in the long run. But when faced with a crisis a blitz of coffee, booze, and long hours is a tempting way to power through. But, with a small growing company, the challenges never end. So take care of yourself. Probably means you say no to a few things and execute better on what matters.
  • Focus. An idea I’ve been getting a lot of mileage out of lately is how startups more typically die from indigestion, versus starvation. As entrepreneurs, it’s hard to resist great ideas. It’s like a buffet. Our job to be “expanders,” chasing what’s possible. A founder like this typically needs a “container,” whose job it is to keep everything organized. I suggest listening to the container a little more. The further I’ve gone, the more I have seen how focus is critical for success, and how a lack thereof can quickly turn the road of trials into the end of the road.

When your dragons show up, take care of yourself. Play your game, forget what makes other people successful, and don’t be tempted to measure yourself against what others have achieved.

In my toughest moments, I had a hard time feeling that I was more than Bluffworks. If the company failed, then I failed. In trying to convince me, my wife finally said, “No offense, but in 10 years Bluffworks will either be a raging success or a somewhat distant memory." Only when I step back to think about my entire life, and dream about the other ventures I plan to start, do I see that she’s right.

Stefan Loble



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