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Creating a legacy project (or why I opened and closed a successful retail line in three months)

Travel is no cure for discontentment of the mind.

There’s something interesting that happens when you’ve reached what people consider “successful” whether it’s because you earn or have a lot of money, have a great job, or get the travel the world, barely working.

You’re not allowed to complain anymore.

Well, you’re allowed to complain, but you’ll get shamed or teased for it.

That’s why when I started feeling a slight sense of listlessness about my life, I didn’t feel like there was anyone to talk to who understood me.

“Do you know how many people want to be where you are?”

“People would kill to have these kinds of problems.”

How do you respond to that? I put my head down and went back to work.

Still, I would sit up at night, laying on my couch, trying to figure out what was missing.

It’s not that my work lacked meaning: on the contrary, I helped banks develop and implement programs that would curb terrorist financing, sex trafficking, and money laundering.

I worked on pro-bono projects and helped build a few nonprofits from the ground up.

I taught mindfulness programs in middle schools to help reduce negative behaviors in students.

Anything with meaning. Anything to feel like I had a greater purpose. But I still couldn’t shake that nagging voice:

What else is out there? I’m bored. I want to do more.

It eventually, turned into: You know what? I want to travel the world. And I don’t want to wait another 10 years for early retirement to do it. I want to go now and start building another business.

In one night (after many agonizing months that turned into years), I decided: I’m going to move to Thailand.

Had I ever been to Thailand? Nope. But I was bored and that should make it even more exciting.

I got rid of most of my possessions, had goodbye parties in three cities, and took off.

And Thailand was amazing. Exciting. Exhilarating. I bounced around nomadically throughout Southeast Asia for a few months. But around month 4, I started to feel that nagging again. Not often. And not loudly. Certainly not enough to keep me up but at night. But it was a slight pang. A feeling of discontentment. Existential dread. With a hint of restlessness. Not for long, and not everyday, but often enough to give me pause.

Sure, I’m happy now, but, what if I never want to settle? How will I ever find a partner if I can’t stay in a place longer than a few minutes? What if I bounce around, nomadically, forever, never being able to truly call a place home? What if I never form a deep, close relationship again?

And on top of that, my own judgemental inner voice joined in: how dare you complain or feel unhappy for one minute? You get to travel around the world, taking pictures, and doing pretty much whatever you want, within reason. What is wrong with you? Will you ever be satisfied with anything?

But just as doing “meaningful work” alone was not enough, “traveling the world” alone was not enough. Pretty pictures, empty writing, stylish clothes and all of the food in the world couldn’t fill the void.

The fact that I had time freedom actually highlighted the feeling: there was no longer any barrier or excuse to shield myself under for not doing the hard stuff.

Imagine having virtually endless time and resources for creative pursuits and wasting it on Netflix.

I needed to create a legacy project: an impactful body of work that was organized around my core principles and beliefs that could stand the test of time.

What constitutes a legacy project?

  • Evergreen content, no matter the medium
  • Long-term, indefinite end
  • Aligned to your core values, beliefs, and principles
  • Outlasts you

Ideally, it should feel like a guiding star. When you have to make a decision, you can always come back and evaluate: how does this align or map to the legacy that I want to create? And every single thing that you create doesn't have to align. It's okay to create things just for fun. But I try to keep at least an 80-20% balance in favor of legacy content.

In 2017, I started a retail line called “affirmations.” There were shirts, tote bags, mugs and other apparel with aspirational language to surround yourself with. It was a perfect stream of passive income and it did fairly well.

But it didn’t map to my beliefs. I practice minimalism. I believe in constant de-cluttering: of the home and of the mind. I couldn’t encourage people to buy more clothes, regardless of how aspirational the text was. So I shut it down.

Finally, after months of road mapping and development and iterations and more iterations, I’ve created:

 Better Living with Design, which includes:

  • Happy, Healthy & Almost Wealthy: a personal development course-based resource for mastering your money, mastering your mindset and mental performance, and mastering your craft
  • smartwork.greatwork.: a positive organizational science consulting-based business for employers who want to improve their employee’s happiness, engagement, satisfaction and move to a state of flourishing
  • intentions.: a planning and tracking resource for dreamers and doers through inspirational planners and digital apps
  • INSPIRE media: an upcoming photo and video-based travel resource that highlights the beauty and culture of different places around the world

Finally, the listlessness is gone. I’m working on projects that excite me so much that I literally have to make myself to go to sleep. Projects that I would work on, even if money weren’t a factor. Building things from the ground up. (In fact, in the process I’ve discovered that I enjoy building things more than running things, which is why I’m working on the home renovation project in Europe even though I may not even live there full-time).

We all like to think that if we had a million dollars, we would go retire on a beach. But if you’re exceptional, the beach gets boring after a week. A month, max.

In spite of the fact that I write about semi-retirement, the goal is not to work less. I actually work harder and longer than ever.

The goal is to work exclusively on things that are meaningful, without having to worry about working for money.

The things you do on Saturday mornings. The project that makes you feel alive. The pieces that stir your soul.

With the exception of tracking for this post on how I spend my time since I semi-retired, I don’t even track how long I spend on my interests anymore. In fact, the other day a friend casually asked me how long my daily 5+ mile walk took. And you know what? I have no idea. It’s like asking me how long I spend listening to music or dancing or drinking coffee. Why would I measure fun? I get into flow, and when I look up, hours have passed.

If you’re reading this site, because you want to retire early or semi-retire and lay on the beach all day: …sure, be my guest. The tools are here.

But if you’re reading this site because you want the freedom of financial independence so that you can finally move in alignment with your passions, your purpose and your calling, then congratulations, you’re in the 5%.

Welcome home.

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