Corey Haines
September 14, 2020

Making The Leap

It’s funny how one conversation can change your life.

Fresh out of high school, a friend and I embarked on a road trip to visit friends in college for the weekend.

With a few hours to spare, we naturally started talking about all our grand plans, dreams, and where we wanted to go in life.

After he explained his master plan to work in sales, start a business, invest in real estate, and take a very non-traditional path in life, he asked me what my aspirations were.

“Mmm, I think my plan is pretty simple. Graduate college, get a good job in accounting or finance, work hard for a long time, retire.”

He responded, “...that’s it?”

In the moment, I was severely offended. But I didn’t reveal that. Instead, I explained my reasoning and we spent the rest of the trip discussing different life paths.

After that conversation, my perspective changed. My eyes were opened. Curiosity sparked. Old dreams were rekindled.

See, my plan wasn’t always “simple.”

Growing up I told everyone proudly that I wanted to be an inventor. Robots, hardware, technology. I liked it all. I considered myself a Lego savant.

I wouldn’t describe myself as a “tinkerer” like many engineering archetypes, but rather an “architect.” Someone who has a vision, creates a blueprint, and then works meticulously to bring that vision to life.

Due to insecurity and my own teenage existential crisis of trying to figure out life and who I am, I decided to take a “safe” route and go into accounting. It wasn’t until the road trip that I realized maybe I didn’t want to take the safe route. Maybe I wanted more. Maybe I wanted to do something unconventional.

Since that conversation, I graduated college, broke into tech, and worked at two great companies.

Now, I’m making the leap and taking the first step toward realizing my own entrepreneurial endeavors.

Friday was my last day at Baremetrics.

I'm going full time creator.

Why now?

They say there’s never the perfect time to have kids. I could see the same being said for starting a business.

I did, however, realize that the ideal time to start and go full time on a business was before having kids and a mortgage. I’d rather risk a few months of savings than my house or ability to put food on the table for my kids. Not impossible, but I’d rather play on “easy mode” if I can help it.

So what’s the plan?

It feels a little like being fresh out of high school again.

Here’s how my friend Corey Gwin described his experience starting to work full time on Blurt.

“...what was driving me to build Blurt was the strong desire to leave my job. Building Blurt and focusing on it after work was like building an escape pod. Now that I've ejected, I don't know where I'm headed. I've escaped, but where to?”

We’ve all heard the “Building a startup is like jumping off a cliff and then building a plane on the way down” analogy. Personally, I feel like it’s more akin to launching into space and then figuring out where you want to go from there.

So where am I going? What am I doing? How will I get there?

Right now, I plan to keep afloat with some light consulting while I work on building up Swipe Files to pay my bills. The eventual goal is to bootstrap a B2B SaaS company. I'll divulge more details soon, but not just yet.

I’ve loosely followed Rob Walling’s “stairstep approach to bootstrapping" which describes taking entrepreneurship one step at a time, each a bit more difficult and rewarding as the last. Certain businesses and business models more difficult and require larger skill sets than others.

What’s the goal?

I recently had the pleasure of chatting with Joshua Levy of Holloway. At one point he said, “I realized that everything around me existed because someone put in the work to make it exist. Then I realized that if I wanted something to exist, I could make it happen if I wanted to. And then I wondered about all the great things we don’t have, that we could, if only someone were to make them happen. What a different world that would be.”

That’s the mark of an entrepreneur. They realize that they want something to exist or for things to work a certain way and so they take destiny into their own hands to try to bring it into existence.

I had a similar realization after spending countless hours listening to podcasts like Mixergy and reading books like Rich Dad Poor Dad and The 4-Hour Workweek. Entrepreneurs are just normal people who take initiative. And if I wanted to bring something into existence, I could. There’s nothing stopping me.

In a peculiar way, I believe the “entrepreneurial itch” is a curse. Once you’ve seen other people do extraordinary things, you can’t unsee it. Once you hear about someone just like you building something similar to what you want to build, you can’t unhear it.

As the old adage goes, “Ignorance [of entrepreneurship] is bliss.”

I have to do it. It would be one of, if not the biggest, regrets of my life.

And like Jeff Bezos, I’m trying to minimize regret.

When I ask myself, “In X years, will I regret not doing this?” the answer is an unequivocal and resounding YES.

But I’m not just trying to minimize regret, I’m also trying to maximize other qualities in my life.

Daniel Pink‘s book Drive introduced a framework that I’ve been obsessed with ever since reading about it. The premise is that motivation has three essential elements: (1) Autonomy—the desire to direct our own lives; (2) Mastery—the urge to get better and better at something that matters; and (3) Purpose—the yearning to do what we do in the service of something larger than ourselves.

Here’s how I think about entrepreneurship through the lens of this framework:

  • Autonomy: Ownership is the ultimate vessel to direct your own life. Make up the rules. Set your schedule. Do things your way.
  • Mastery: Double down on your strengths and delegate weaknesses. Choose which skills you want to improve. Choose what you work on and how much you work on it.
  • Purpose: Enable a lifestyle that aligns with your values. Use profits to give charitably. Provide value to customers.

The truth of it is: I’m just not that motivated by extrinsic rewards—money, status, titles, recognition. Intrinsic rewards—autonomy, mastery, purpose—are what drive me.

Daniel Vassallo asks, "What kind of work would I do if I had to do it forever?" in his blog post Only Intrinsic Motivation Lasts.

I don't want to be an employee forever. I want to be a creator.

It's going to be a lot of work, but I'm playing the long game.

And the journey starts today.

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