The only way to live the life you want is to design it

My evolution from working 24/7 to intentionally designing all aspects of my life around maximizing happiness and enjoyment.

Hi, it’s Melissa, and welcome to “your founder next door”, a bi-weekly column with relatable stories of my journey bootstrapping eWebinar to $5m ARR. No BS, just straight-up truth bombs on what it’s like to build a company without an abundance of resources or friends in high places.

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In 2017, David and I left New York to travel full time as “digital nomads”. I was running my second company, Spacio, and he was a fractional CTO for startups. We both worked remotely (way before it was cool) so we thought that instead of paying $3500 for a room in the Manhattan co-living house I was managing, which was turning into a Big Brother reality show…we’d redirect those funds to renting Airbnbs around the world.

That was the first decision I made for me since I founded my first company in 2011. After years of struggling, chasing debt, and paying other people’s bills, Spacio finally broke even and I started paying myself a meager salary (~$40k). For the first time, I was coming out of survival mode and had the mindshare to ask myself what I wanted. I asked myself, if building that company was going to continue being hard, what is something I could do for me?

I hadn’t traveled much up to that point and had always wanted to. It was a good time to start, especially since I had a life partner that would make exploring easier and more fun. I pitched the idea to David and it didn’t take much before he hopped on board. We put a few boxes in storage and took off with hand luggage and a backpack to our first of many destinations, Chile.

That period of nomading lasted 3 years and it was the most profound experience of our lives – it was a journey of exploration and self-development. We discovered Amsterdam, the place we now call home. We discovered music, partying, and community, the things that give us the most joy and contentment.

Most importantly, that decision was my first taste of “intentional life design”.

Work used to be my entire life 😰

My dad was the hardest worker I’ve ever known. He was a workhorse who hated his job for as long as I could remember. He spent 40 years in the same company and worked his way up from an office boy. He gave us a great life, but suffered through it even though it gave him purpose. He’d say, “I sacrificed everything for you all.” I felt accountable for his pain and carried that guilt for a long time.

He was the one who taught me to have an incredible work ethic – perhaps too incredible.

It was engrained in me early on that if I wanted to be successful, I’d have to work just as hard as him, or even harder. Hearing my dad complain about his job every day normalized the idea that work is supposed to be difficult, and that you’re not supposed to have a good time doing it.

My parents told me that good grades would lead to a good job, working hard would lead to promotions, money, success, and happiness. (I later found out this was a lie when I learned that I didn’t need much to live large.)

I was always the teacher's pet, in school and at work. I put in the most effort and the most hours, and I always cared most about my performance and output. This professional intensity was accelerated when I started my own business because I had bills to pay and a team I was  responsible for. Because I was bootstrapped and never had disposable income, I stopped socializing and dating. I channeled all my energy and resources into work because I wanted to win so badly. As a result, I missed out on life events like numerous bachelorette parties and weddings. My entire life was my startup.

For years at Spacio, we weren’t doing well and I had a lot of founder guilt. I worked more for the sake of working and showing my team that I was always on it. I barely took time off and felt bad when I did. When I did anything fun, I’d try to hide it from my cofounder. I felt guilty for not achieving the success I had envisioned, so I overcompensated by working all the time. Carrying this guilt stopped me from being happy with the effort I was putting in every day. It made me feel like I was never enough. It was mentally exhausting, but I did it anyway because I was a machine that could not be defeated. Everything was fine, it was supposed to be hard because there’s a pot of gold at the end of the rainbow, right?

The only way to live the life you want is to design it 🙌

When we left New York to experience the world, I finally realized that there was more to life than building companies. I had given up living for so long that I didn’t even remember what it was like to have fun. Since I was no longer surrounded by other founders, I was no longer talking about my startup 24/7. It was refreshing and liberating. Turns out, in places like Europe, people don’t even ask you what you do because they don’t care! Imagine that!

It took me years to realize that working more doesn't mean you are more productive or that you'll be more successful. I didn't need to work more, I needed to work more creatively. You can only do your best every day, and that is enough.

With the weight off my shoulders from breaking even, I started to work more normal hours and took evenings and weekends off. Guess what? Revenue did not take a hit, but my wellbeing significantly increased.

Building my startup didn’t get easier, but I was finally having fun (in other aspects of my life) while doing it. All my life up to that point, I thought my dream lifestyle was the end goal…the final reward for success. I was waiting to achieve it like unlocking another level of a video game. Had I continued to wait, it would have never happened.

Deciding to change my circumstance by nomading taught me the most important philosophy that has since formed the foundation of my life:

The only way to live the life you want is to design it

When we were traveling, friends would ask, “How do you do it?”

There’s no secret. I simply decided to make it a goal to design the life I want to lead.

Having goals allow you to do 2 very important things:

1. Say yes to the things that take you closer to it

2. Say no to the things that don’t

It’s incredible how much of your life you actually can have control over if you decide to take control of it. It might not happen overnight, but there is so much of your life you can craft by being mindful of what you say yes and no to.

I stopped pretending to be in the same time zone as my customers. I openly talked about my travels and lifestyle, and those became fascinating conversations because most people lived conventional lives. I did my best to group live calls on certain days as I was often halfway across the world. My business continued to grow, and Spacio was acquired in 2019. One of my key requirements for my acquirer was that I got to keep my nomadic lifestyle.

Designing my next startup around what makes me happiest 🤩

My first two startups were in real estate because that’s where my experience and connections were. Conventional wisdom said that I had to do something I had unique insight into, so that’s what I did. I built a career on top of what I knew because I thought that's what I was supposed to do. It never even occurred to me that I could do something different. I never loved the industry and hated dealing with real estate agents, so in turn I was never that happy for 10 years of my life.

After Spacio, I asked myself why my job always felt like a chore despite having wins along the way. I realized something important. At 18, we’re told to pick a major so we can find a job, build a career, then find happiness after. If you envision this as a pyramid, your education and expertise is at the bottom, your career sits on top of that, then happiness on top of that.

How can we expect that what we choose in our teens is the same passion we have 10, 20, 30 years later? I believe most people end up hating their jobs and living for evenings and weekends because they build their career on the wrong foundation – they build it on their expertise instead of their happiness. We’ve been conditioned to make life choices this way, and I also fell into the same trap.

What if we inverted this pyramid and put happiness on the bottom? What if we first identified what made us happy, then found a career that serves our happiness, then learned the skills to build a successful career?

Two months after Spacio was acquired, I wanted to start a new company because I didn’t get a retirement level exit and didn’t want to work forever. I decided to take this new approach by designing my next startup around what would make me happiest instead of my past experience, knowing full well that I’d be able to acquire the skills to make it successful.

My time with my first two companies taught me so much about what I wanted and didn't want to do in a business, and what kind of product would allow me to prioritize my happiness over being constantly tied to my startup. I wrote down a list of 10 non-negotiables that I needed in my dream lifestyle, and that list helped eliminate 95% of the ideas I had. 

The Product 📋

1. Must be able to be sold 100% through the internet (No more conferences and booths)

2. Cannot be limited by geography, language, industries, and lines of business (Spacio served a really niche market)

3. 100% web-based, no apps

4. Has to have a proven market (No blue ocean)

5. Potential for high financial ROI (Relatively low/predictable investment vs. potential revenue)

6. Super easy for anyone to understand (Including a 12 year old)

The Team

7. Fully remote team, no employees

Me

8. Create something I can be excited about every day (something that makes a difference)

9. Build a business/product that is a reflection of me

10. Be able to share our successes with friends

I chose eWebinar because it was the product and business that fully aligned with the life I wanted to live. As a result, even when things are hard now, I know that I am serving my happiness and that's what makes this journey so much more meaningful than my previous ones.

Your company becomes such a big part of your life that if you don't start by intentionally designing it around your own happiness, it'll just be that much harder.

Put yourself first. Don't make the same mistake I did.

Reflections 🪞

While I started designing my life with the goal of traveling more, I realized that having control over my time meant making room for new experiences, friendships, and connections I wouldn't otherwise have had.

If I can design the life I want to lead, you can too.

There are only 3 steps you need to take to make this a reality:

1. Decide to make life design your goal

2. Say yes to the things that take you closer

3. Say no to the things that don’t

Intentional life design is not an all or nothing concept. It’s a process of continuous improvement.

Recently, someone asked me to share a moment in my journey that I'm most proud of...

💡 That moment is RIGHT NOW.

14 years ago, I walked out of my last job without a plan other than wanting to forge my own destiny. I left my cubicle that day and decided to design the life that I wanted to live. I set out to find a career with limitless potential that would allow me to work from anywhere in the world. I had no idea what that life would look like, I just wanted to go there.

After all these years, I can finally say that I am now living the life I once dreamt about.

I have 100% control over my schedule, a growing business that pays me a good salary (for the first time ever this year), work with a remote team that self-manages, a thriving social life, and a loving partner who’s also my cofounder. While I don’t have everything I want, my life is not lacking.

It took a long time to get here. There were so many ups and downs. This has been nothing short of a great adventure.

To quote my favorite book, “What is the world’s greatest lie?” the little boy asks. The old man replies, “It’s this: that at a certain point in our lives, we lose control of what’s happening to us, and our lives become controlled by fate. That’s the world’s greatest lie.”
 — The Alchemist by Paulo Coehlo

Some stuff you might find interesting 👇

• The 10 non-negotiables that led me to start eWebinar

• Design the life you want to lead (not around the next demo)

• How much is enough to stop working?

• My guest post on Kyle Poyar’s Growth Unhinged: The 10 biggest mistakes I made bootstrapping to $1M

• New Profited episode, S2E19, 12 $0 Marketing Strategies

Thank you for reading!

Melissa ✌️

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