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

Stefan Loble

Making a career change at 40 — or at any point in life when you’ve accumulated a lot of responsibility — is hard because the stakes are so high. Many of us dream of becoming an entrepreneur and working on something we truly love. I certainly did.

But later in life, a lot of things can stand in the way; mainly in the form of responsibility. It would have been a hell of a lot easier to make the leap in my 20s, when I had fewer people relying on me and could have lived more cheaply while I got my dream off the ground.

It turns out, there’s a pattern that defines our biggest quests. It’s called The Hero's Journey.

Written by Joseph Campbell, his observation was that all great stories -- from ancient Greek mythology, to what we watch today online -- follow a similar pattern.

"a hero ventures forth from the world of common day into a region of supernatural wonder: fabulous forces are there encountered and a decisive victory is won: the hero comes back from this mysterious adventure with the power to bestow boons on his fellow man."

Why is this relevant to you and me? Because when we march off an take on something big… either a midlife career change, or even an intimidating overseas trip… it turns out the roller coaster phases of ups and downs, and seemingly insurmountable trials are all normal. Where stories mirror real life, The Hero's Journey got it spot on, and knowing this can provide comfort, and a measure of guidance along the way.

So here goes: a roadmap for adventurers. I have broken this into four phases:

Phase I includes The Call to Adventure and Refusing The Call.

Phase II is Crossing The Threshold and Meeting the Mentor

Phase III is the Road of Trials

Phase IV is Returning to the Real World


The Call To Adventure: Facing a difficult choice.

The journey begins with the call to adventure. Something that makes you want to leave your warm bed to wager health and treasure in pursuit of something great. Make no mistake: in entrepreneurship, both are at risk for real, because many of us have a nasty habit of working ourselves into the ground.

For me, when my work circumstances changed after thoroughly enjoying a 20-year career in software, I became miserable enough to search for an alternative path.

I was looking for freedom and wanted to align my work with what I love to do = travel and pursue my own ideas. My escape was to dream of a big change, of starting my own company to make products I loved and connect with other people passionate about travel around the world.

Looking back, I would argue that most of the changes we make in life come from discomfort with the status quo. When things are good, what is there to dream about? Which means you too may be initiating your quest from a position of weakness. A situation you're dying to leave. It happens to many of us, and you may feel something between a mild loss of purpose, to all out I can’t stand it anymore, frustration.

When I cried in a stairwell at work, I vowed that something had to change. And at that moment, I accepted the call and transformed from dreaming to actually doing.

The Key:

This step is all about hearing the call. The most important outcome is that you get on the road to change, but take on the right adventure. Here are a few tips:

  • Be specific about your goal. You need to be clear about what you’re trying to create versus what you’re trying to get away from. For example if my goal had been starting a company so I could be my own boss and have freedom to travel, I would have been sorely disappointed, as being a CEO can often bring more responsibility, not less. I just marched off, and began pursuing my idea. You should think about what you’re getting into.
  • Kill bad ideas. I am an idea factory (they won’t stop coming) which means I have to kill bad ideas all the time. And you should too. In other words, be careful not to get too attached to something you may love, but doesn't have the economics to work over the long term. Later in life, careers that don’t pay the bills, punish your body, or take you away from family can cause real problems, no matter how well they align with your passion. I know you may be miserable in your current situation, but chose your next adventure wisely.
  • Calculate your risk. Understand there is a big difference between starting a one-person business, supporting a hobby on the side, and building a full-fledged company that you’re going to scale. These things require different levels of commitment and resources. And when they get rolling, the effect on your life can be dramatic, in terms of managing employees, satisfying investors, etc. Once you’ve started down the path, there may be no turning back and when the inevitable crises occur, the pressure you feel is greater, the bigger the thing you’ve taken on. For goodness’ sake, talk to someone who has done it before. 

I hope you exit this phase with unbearable excitement, all ready to go. But also, with your entire livelihood and happiness possibly at stake, choose the right adventure to pursue.

Refusing the Call: And how to get over your fear

The flip side of being thoughtful when hearing the call to adventure is gathering the courage to take the decisive action needed to make it happen. If the path for you to move forward is clear, then you don’t have a problem. But later in life, when you’re thinking “I need a new career,” your life probably comes with strings attached.

We all have barriers between us and our biggest dreams that feel uniquely intractable, and real. Your problems are real. But to move forward, you have to realize that on a global scale 1) they are not that unique, and 2) other people have solved them before. So can you.

My big breakthrough came when I had coffee with a friend and I told him about my dream of starting Bluffworks, with an equally passionate description of all the things standing in my way.

Finally he said, “Stop saying can’t. What time does your wife go to bed? Kiss her goodnight and go back to work.”

That was HUGE and I went and I did it, working on my dream as a side project alongside my day job for over two years until I was able to go fulltime. It turned out, none of my roadblocks were insurmountable, but in the moment, I was too close to see what I could do to overcome them.

The Key:

This step is about throwing yourself into the adventure. Here are a few tips:

  • Break down your wall. One good way to dismantle what’s holding you back is to reframe your life, so you can identify wasteful uses of time or money that could be directed to your project. I suggest your calculate your needs backwards, by rebuilding your life up from zero. Start with nothing, and put back only those things that really match your priorities. I gave up a beautiful apartment and moved in with my parents for a summer (me + wife + 1-yr-old son) while attending classes in fashion, and holding down a day job; all to fund the start of Bluffworks from my current income. It was a sacrifice, but set me on a completely different path from a another me in a parallel universe who could have accepted the status quo. At the same time you’re feeling stuck, there’s probably fat to be cut in other parts of your life. It’s about choices.
  • The risk of inaction. I often hear about a creature that has the potential to bite your head off later in life — and that monster is regret. Many mentors and authors I respect suggest that as you get older, regret can be a persistent pain. So as scary as action feels now, inaction can have pretty terrifying consequences, too. I’ve sometimes looked back at prior months and thought “wow, what if I was studying French everyday, or doing more pushups.” Bigger things are possible if we try. 

I hope you exit this phase by getting on your horse, and break through barriers to see your way forward to making that big trip, changing your career, or becoming an entrepreneur.

I can’t tell you it gets easier from here. In Part II you’re still preparing when you Cross The Threshold and Meet The Mentor. Part III, about the Road of Trials is very hard. Only in Part IV do you get to (hopefully) Return To The Real World with spoils in hand.

I estimate the only reason I’m able to even write this post is that Bluffworks is beginning to hit its stride. With the success of our blazer last year, and next month's highly anticipated dress shirt release, we're on a roll.

But in hindsight, becoming an entrepreneur at 40 was the toughest thing I’ve ever done.

I hope this roadmap spurs you to action, and along the way makes you feel less alone.


Stefan Loble 



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