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

Stefan Loble

Stefan rock climbing in the Meridian Shirt.


Becoming an entrepreneur at 40, or any time in midlife, comes with its own set of challenges and rewards that are different from walking the road when you’re young, carefree, and with fewer obligations.

In Part I of this series, I talked about the journey to starting a business being similar to the famous literary Hero’s Journey. Like Luke Skywalker or Harry Potter, we hear the call to adventure (in this case, changing careers or starting a business) and at first refuse the call — it’s too hard, too scary, not for me.

Now, Part II is all about commitment and taking action. We’re no longer dreaming of what it might be like to start a business… We’re actually making moves to make it happen.

It’s worth talking about action for a moment. Taking small steps — like registering a domain name for your budding business ain’t it. This does not count as true action, and is as far as a lot of people ever get, the point at which they lose interest and abandon the quest.

Instead, I’m talking about real steps, where your begin to spend hours and days on your business.

This is the time to GO FOR IT! Do it for real. Make the commitment and jump in with both feet. Half-assing it isn’t going to get you there.

Crossing The Threshold: Turning the dream into reality

This is it: The moment you commit to turning your dream into reality. It’s time to go. But, I’ve noticed that crossing the threshold happens not when you start the work, but when you become fully committed  — and the quest really starts to really get its hooks into you. You’ve passed the point of no return and there’s no turning back.

One thing I’ve noticed is that you’re truly serious when you are willing to speak publicly about your idea. In the beginning, I was reluctant to share my plans with the world, afraid that someone else would try to step in and do it first. But there is a point where you become the one person in the world who is the most passionate and serious about that idea, that all other imitators would be left behind.

The Key:

In this phase, you need to demonstrate that your commitment is well placed through a combination of proving your idea and managing how you allocate resources.

  • Test your idea. You want to validate it so you can confidently commit. Software has a concept of a minimum viable product (MVP). To get feedback and get a proof of concept, developers release a product so early that they’re ideally “embarrassed” by it. This is harder to do without consequences in physical products, but whatever you’re creating, your goal is to find out: “does my idea have legs?” I once wrote a blog post about the worst reactions to a great idea. People said to me, “Wrinkle free pants? Aren’t those Dockers?” No one can tell you if your idea is a good one. The only way to know for sure is to prove it. And if it doesn’t have legs, you want to know as soon as possible so that you can iterate.
  • Plan for reality.  Here’s the deal — if you’re an entrepreneur, and are good at seeing possibilities, you probably have a blind spot in seeing limitations. That’s the way it works. Our strengths have corresponding weaknesses, and guys like us who dream big can do so because we can suspend recognition of the bumps it will take to get there. That’s certainly how I’m wired. The result is your quest will very likely require more time, sacrifice, and treasure than you are planning for. It took me two-and-a-half years to leave my day job even after our original Kickstarter went zoom, raising $128K in 35 days. I think you should go for it, but fill your pack with the resources you need for your climb. Companies fail, and people die on journeys. Preparation can help reduce the chance that it will be you.

Meeting the Mentor: Assembling the team for your quest

The number one thing I wish I had realized early on in my journey is that I was going to need a lot of help.

For example, if you’re building a house, you know you’ll need help. It’s a tangible, easy to visualize challenge that you’re loathe to take on alone. But when planning a business venture, it’s easy to pretend you can do it on your own, as intangible cerebral activities (like marketing, inventory management, strategic planning) have a nasty habit of hiding how much work there is — particularly when you haven’t done them before.

For some reason, I find it grounding to remember that to succeed in business, you have to defy something. Whether it’s existing technology, the competition, or the marketplace, a new company or idea has to outpace something that already exists or no one has done before. This means it’s hard. And why on god’s green earth would you take on something so difficult alone?

The Key:

In every story there is a wise mentor and a band of merry men. The key is to know your weaknesses and don’t try to go it alone.

  • Compensating for your weaknesses. The relationship between strengths and weaknesses is real. When I was younger, I (arrogantly, and inaccurately) thought the best team would have been a bunch of MEs. But with more experience, I realized that the various members of a team could never do each other's jobs; a salesman and a software developer — we needed them both. You have your zone of genius, so find a team that can handle all the other things that need to be done so you can focus on that zone.

Once you’ve crossed the threshold and you’ve met the mentor, you’re really in it. You’re no longer just talking about or taking on your big dream: you’ve made the leap. It’s scary, but I can say from experience that it’s worth it.

The more successful my business has become, the more proud I am that I did it, the more gratitude I feel towards our customers, and the more pleasure I can enjoy from getting them products that make a difference.

But I’ve also learned that success is not a flash in the pan. It comes from a long-term commitment to action. Boy, am I a different person from when I started.

Next up: There are trials ahead. Part III is when you meet the dragons between you and your ultimate goal. Hang on tight.

Stefan Loble 



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