One journey ends, and another begins

The background story on why I created the Serendipity mindfulness journal app.

In early 2015, my life and my health were on a crash course for disaster.

By all outward appearances, things had never been better. I was a founder of a wildly successful startup worth billions of dollars. My relationship with my wife and kids was idyllic. We had just moved into a dream home.

But at work, things had become unbearable. The company expanded so fast and a wave of new executives were hired who I didn’t get along with. I was in a constant state of fight or flight. I wasn’t sleeping. I was drinking too much. All of that was wreaking havoc on my my mind, body and soul. And it was starting to affect my relationship with my family. I ended up making an extremely difficult and heartbreaking decision to leave the company I founded.

Before I resigned, I took a 3 month hiatus, just to be sure I wasn’t suffering temporary burn out. During that time I focused on healing and recuperating mentally, emotionally and physically. I did my version of an “Eat Pray Love” journey. We did a family campervan roadtrip around New Zealand. Then I went to visit my brother in Mexico, where I learned to surf. Finally, my wife and I went away to a meditation retreat.

It was awesome and definitely very restorative.

Along the way I read Eckhart Tolle’s “Practicing the Power of Now”, a seminal tome in the canon of mindfulness and self-help. The book was hugely helpful in giving me the sense of perspective and priorities I needed. It also reinforced what had become the inescapable truth: I had to resign.

It was a monumental decision, after a monumental journey. This company I started dominated my life for nearly 10 years, I helped it grow from a couple of people crammed into a tiny apartment to 1,000 staff in 18 cities around the world. And suddenly that journey ended for me.

I had a vague idea what I would do after I quit. But the universe had different plans.

And thus began the journey to creating Serendipity.

Dark days

When I quit the business, many people thought I was financially set for life. That would have been nice, but it was far from true.

However, we were in a good position financially. We had enough money so I wouldn’t need to work for a few years, if I didn’t want to. And I didn’t want to. I was exhausted and I really couldn’t handle getting back into the game any time soon.

The financial freedom was a wonderful dream come true. But it was also surprisingly unsettling. I could do anything I wanted, but all I wanted to do was go surfing. That was fine, for now. But I knew eventually I’d need to start working again in a few years. And in the tech industry, being out of the game for just a few weeks will leave you in the dust.

I didn’t need to worry too much, because that financial freedom didn’t last very long. Almost immediately after I quit, something I’ve dreaded my whole life happened.

Something went very wrong with our taxes (long story short: we have a complicated tax situation because we live overseas). As things unraveled, it turned out we owed the IRS a mind boggling amount of money . Enough to pretty much wipe us out completely.

That rattled me to the core. All my deepest fears came crashing down on me. I was an absolute wreck.

The road to recovery

To help me cope with the emotional turmoil I was experiencing, I started regularly going to a meditation class. It was really the first time in my life that I regularly meditated and it was extremely helpful.

But even with all that, as my financial situation unraveled, I had some of my darkest moments in life. It felt like my existence was under threat. Everything I worked so hard to accomplish was about to be taken away.

My worst fear was that I would have to start over, from nothing. And I was too old for that shit.

Back to basics

They say money can’t buy happiness, and that’s certainly true. But our family was so much happier with money than without it. Before we had money, we struggled for years, sometimes not even being able to afford groceries. It was exhausting and demoralizing. Once we had money, suddenly a huge weight was lifted. We were to able to enjoy life much more — we could eat well, live in a well heated comfortable house, and take family vacations to visit friends and family back in the old country. We also got a few new toys that were fun too.

It seemed all of that was going to be imminently taken away.

Keeping some perspective

The first and most important bit of perspective I needed to keep in mind: losing money is far from losing everything. My family is the most important thing in my life, and that wasn’t going away. And generally speaking, we’re all pretty healthy. If we lost all our money, we’d still have each other and that’s a lot to be grateful for.

Gratitude

I’ve known from past experiences that having gratitude is essential to keeping perspective and also recognizing things are better than you realize. Gratitude for my family and friends. Gratitude for the opportunity to have been able to experience success in the first place. Gratitude for the expertise and skills I built up that are still extremely useful and valuable. Gratitude to be living in a beautiful country where I have incredible opportunities to build a wonderful life. The list goes on and on.

Sleep on it

Sleep is normally an easy and great way to let things settle down and get some perspective. But therein lied the crux of my problem: I basically lost my ability to sleep through the night. At best, I could get a few hours of sleep most nights, but it was far from 8 hours and it was far from restful. And in those sleep deprived hours, crazy dark shit tends to haunt your thoughts.

So as a proxy for having the perspective of sleep, I learned another technique that helped me: I had to compartmentalize. At night before bed, when my anxious thoughts tended to be the worst, I told myself “What you’re worried about is legitimate, but there’s nothing you can do about it now. Thinking about it now will make things worse, so just leave it until tomorrow. Now it’s time to rest.”

Getting mindful

That compartmentalizing really is a form of mindfulness in practice. Focus on what you’re doing, in the moment. If your thoughts drift off to something that isn’t happening right now in the moment, gently bring your mind back to the thing you’re doing. So when it’s time to sleep, my thoughts should be on getting some rest. I don’t even pressure myself to “sleep now!” — which has the opposite effect — I just focus on getting some rest.

Staying mindful

All these techniques worked, but they were just the ambulance at the bottom of the cliff — ways for me to cope after my fears and anxiety got out of control. I really needed a tool to help me practice mindfulness continuously, throughout the day, every day.

No, there really wasn’t an app for that

I looked for apps to help me with practicing mindfulness, and I tried lots of them. But none of them really inspired me or engaged me. Most of them were meditation apps, simply re-branded as mindfulness, none were focused on understanding and practicing mindfulness.

So I decided to create one for myself.