One of My Biggest Regrets: Wasting Years of My Life

"And then one day you find, ten years have got behind you..." - Pink Floyd (#37)

Midjourney prompt: ticking away the moments that make up a dull day

Everyone has regrets. If they tell you otherwise, they’re lying, delusional or both.

One of my biggest regrets is the years I wasted in my career. It was particularly bad from 2001-2006. I was coasting. At the time it didn’t always feel that way. I was putting in lots of hours, working hard, stressing out. But I wasn’t getting anywhere. Very little progress or learning took place in those years.

During that time I got married and had my first son. I was making decent money (at least by my standards.) Life happened and it was good. Comfortable. (Although having kids is anything but easy—that part was completely insane!)

Comfortable is OK, but if you’re an entrepreneur it’s actually the opposite.

In my case, comfort became coasting, which became giving up. The company I was working for at the time (which had acquired my small web agency in 1998) wasn’t scaling. We were stagnant. We tried a bunch of things to generate more growth, but very little worked. Still, we plodded along.

The owners of the company seemed more OK with the situation than I was. They weren’t doing backflips of joy, but they weren’t raising any alarm bells either. What we had was a crappy lifestyle business that wasn’t generating real profits (or dividends), with no real plan for how to scale. And suddenly that great salary from 2001 looked pretty mediocre in 2006.

Sidebar: I have nothing against lifestyle businesses

Frankly, the term “lifestyle business” doesn’t do justice to all the non-venture funded businesses out there that are absolutely crushing it. The effort to build those businesses can be enormous! It’s not as if building a non-venture funded business automatically equates to tons of free time and perfect work-life balance.

Somehow “lifestyle business” became a dismissive term, which is ridiculous.

If you can build a business with no venture funding and generate yearly profits, pay yourself a great salary and spit out dividends—what’s not to like?

I know more and more entrepreneurs that are buying businesses or building businesses without any outside funding (other than loans.) They’re not going to venture capitalists or angel investors and putting themselves on a pathway to
”unicorn status or bust.” (btw, I don’t think these are the only two options for venture-funded startups either, nor do I think venture capital is bad or evil, but there are options.)

There are tons of ways to build great companies; venture capital is most definitely not the only path.

In my situation, we didn’t raise any capital and we couldn’t grow enough to move the needle. Perhaps we should have raised VC, but we weren’t connected at the time.

The business stagnated not because it was a lifestyle business, but because it was a bad business.

Midjourney prompt: stuck in the mud

For about 5 years of my life, I didn’t progress professionally. Fuck. What a waste.

“If you’re not moving forward, you are moving backward.” - Mikhail Gorbachev

When I finally decided to move on I had no idea what to do. Get a job? Start a company? One of my biggest challenges was that I didn’t have a network. The Montreal startup community (where I lived) wasn’t very big at the time. But I had also grown apathetic. The company wasn’t successful, I felt like a fraud, and didn’t know where to turn.

Instead of turtling, I went in the opposite direction. I started blogging. I put myself out there, shared my knowledge and experience, and built a network.

Literally everything I’ve accomplished since 2006 is because of blogging.

By forcing myself to get out there I met tons of people virtually, and built a local network as well. I’m not suggesting everyone should start a newsletter or publish long form content, but you should connect with both online and offline communities.

Networking and building a brand remain the best ways to open yourself up to opportunities. You put value out into the world and sometimes good things come back.

After 2006, I promised myself I’d never get caught standing still again. Time is simply too precious.

Fast forward to 2014.

The company I worked for, GoInstant, had been acquired by Salesforce. We were two years into the acquisition and working to integrate our technology. It was an incredible experience. I learned a ton. But it was also very challenging.

After two years things started to stagnate. It became clear that the only path in Salesforce was levelling up the career ladder, which would realistically require a move to San Francisco. I didn’t want to move up the career ladder at Salesforce and I didn’t want to move to SF either.

I had one year left on my golden handcuffs. I could have gone into cruise control, stayed at Salesforce for a long time, and earned a lot of money. Instead, I left. As a result I left millions of dollars on the table. To be fair, I was lucky enough at this point to have a decent amount of money, but I wasn’t super rich by any stretch of the imagination. The money I left on the table would have been very meaningful. But I knew I was spinning my wheels and wasting time.

And time is too precious to waste.

I was unhappy and didn’t see a meaningful path forward at Salesforce. And I was scared about being stuck doing something that had no real future for me, despite the economic benefits. My kids weren’t in high school yet, so my wife and I felt like it was still a reasonable time to move before the kids got really pissed at us about it. We had only moved two years prior, and wanted some level of stability.

We decided to move to Toronto and I joined VarageSale (where I was one of the first angel investors.) I thought to myself, “No matter what happens at VarageSale, Toronto is a big startup ecosystem, I’ll always find something to do.”

VarageSale was a true rollercoaster. I was only there for a year and a half before I was let go. I learned a ton and don’t regret the decision to move from GoInstant/Salesforce, although the outcome at VarageSale was not what I was aiming for.

I won’t lie—I think about the money I left on the table with Salesforce—but I still believe the decision was the right one.

I know people who are unhappy but make a lot of money and stick with it. I simply can’t do it. It’s not that I won’t grind through tough times, or push myself beyond what I think I’m capable of. But I won’t sacrifice time in exchange for money if I’m truly and consistently unhappy or stagnant.

Don’t say “no”, say “yes” :)

I’m now 48 years old.

The average life expectancy for a Canadian man is ~80 years old. That means I’m 60% through my life. Shit. 😃

My kids are 16 and 18. In two years, assuming my 16 year old leaves the house, my wife and I will be empty nesters. Holy shit. 😨

My dad often says to me, “Time moves faster as you get older.” It doesn’t, but your perception of time absolutely moves faster. Actually, it gets scary fast.

There’s no time to waste.

You can make money, lose money, succeed and fail—just do it all quickly. Don’t spend time overthinking every decision. Don’t spend time treading water. You most certainly will have to do things you don’t want, or things that make you unhappy—life is simply too hard and complicated to be winning all the time—but wasting time isn’t an option.

From a practical perspective, the race against the clock has ingrained a few things in me that I always try to remember:

1. Do things that matter

Midjourney prompt: your heart of hearts

Why would you waste your time doing things that don’t matter?

No one does that intentionally, but it’s easy to fall into. Humans are great at deceiving themselves. We can convince ourselves of almost anything, even if we know in our heart of hearts it’s nonsense.

What matters to you will differ from someone else. I’m not suggesting you need to stop what you’re doing and figure out how to cure cancer or save the planet. But ask yourself this:

• Am I learning anything meaningful?

• Am I challenging myself in a way that will help me get better?

• Am I doing what I’m doing because it’s expected of me, or because it’s what I want to be doing?

• Am I enjoying myself?

• Am I moving in a meaningful direction?

There’s a reason I ask every founder, “Of all the things you could be doing with your life, why this?”

2. There is no map

I’ve met people who map out their entire careers from the day they go to college. Some of them do exactly what they planned / envisioned, which is incredible.

• For most of us, there’s no map.

• For founders, there is 100% no map. I wouldn’t even bother looking for one.

Even if you follow a map, I’m quite certain that you’ll change directions along the way. Career planning is fraught with many variables. Life has a tendency to get in the way.

When I revisit my career it looks like one random jump to another. In some ways that’s exactly what happened, but it’s because I remained open to possibilities. I stayed curious, met lots of people, challenged myself and figured, “What the hell? Let’s go try that now…”

3. It’s all about the sets & reps

Midjourney prompt” sets and reps, comic book style

The more shots you take, the more shots you make.

Maximizing your time is about increasing the frequency of sets & reps. I spent years doing the same thing over and over, but not in a good way. I wasn’t mastering a craft, I was phoning it in.

When Lean Startup came out it changed my life. It has a core concept of Build → Measure → Learn, which you execute in a cycle. You do something, measure the result, learn and iterate. It’s brilliant!

• The more you go through the cycle, the faster you learn.

• The faster you learn, the faster you figure things out.

That’s how I think of sets & reps. You have to keep trying things, quickly, and prescriptively (not just wandering around “doing stuff”.) There’s nothing worse than filling your time with pointless shit to feel busy and useful, only to realize you wasted your time (and probably other people’s time as well.)

4. Everything has an opportunity cost

Everything you choose to do means you can’t do something else. That’s an opportunity cost. You may not even realize you’re making a choice, but it’s happening.

Sometimes the opportunity cost is a straight up sacrifice. If you’re a founder you know exactly what I mean, especially if you have a partner, kids, family, etc. Every founder makes sacrifices. Hopefully your sacrifices aren’t so severe that they cause major issues. But I know that happens a lot.

You’re not alone; other CEOs feel the same way

I surveyed 69 CEOs about their experiences, and shared the results here: The Startup CEO Job is Intense, Lonely, Rewarding & Crazy

I somehow managed to find some degree of work-life balance, but it was never easy. I made choices that resulted in other people having to pick the ball up for me (namely my wife.) That’s still happening today. And I’m keenly aware of the sacrifices I’ve made (and not made) throughout my career.

When you recognize that everything has an opportunity cost, you have a chance of making more intellectually honest decisions.

You can be brave in the face of constant uncertainty. You can be sensitive to the choices you’re making and the impact they’re having, but still make the choices.

You can force a decision, instead of letting it languish or pretending it doesn’t have to be made. I see a lot of founders in zombie startups—they’re dead but still shuffling ahead—because they can’t make the tough choice. The absence of a choice is still a choice, and if you’re in a situation that’s not going anywhere, relying on miracles to save you, you’re wasting time.

You Can’t Be On All the Time

Midjourney prompt: sitting in a dark room with one single lightbulb on, comic book style

Maximizing the time you have doesn’t mean you’re executing 100% every minute of every day.

Everyone needs to turn off.

Everyone needs to “waste time.”

A lot of creativity and inspiration comes from the moments “in-between” the work.

Please don’t take this post as a rallying cry for over-the-top hustle culture. It’s not.

Admittedly, I’ve slept at the office before (it’s been ~15 years though!) and worked insane hours. The grind is real. I don’t have a problem working lots of hours when I believe in something. But it’s not sustainable. Burning out is a terrible way to waste time and has other serious implications.

In 1994 I saw Pink Floyd play in Toronto. One of the big moments in the concert was when they played Time. The song starts with a bunch of clocks and alarms chiming loudly. The acoustics were amazing, with clocks ringing all over the place. I still listen to Time today. The lyrics are a good reminder of…well…time. 😃

Apparently, Roger Waters “got the idea when he realized he was no longer preparing for anything in life, but was right in the middle of it” (although he was only 28 at the time!) ¹

Don’t waste time.

Time by Pink Floyd

(The video is from 1994, but not Toronto.)

Ticking away the moments that make up a dull day
You fritter and waste the hours in an offhand way
Kicking around on a piece of ground in your hometown
Waiting for someone or something to show you the way

Tired of lying in the sunshine
Staying home to watch the rain
And you are young and life is long
And there is time to kill today

And then one day you find
Ten years have got behind you
No one told you when to run
You missed the starting gun

And you run, and you run to catch up with the sun
But it's sinking
Racing around to come up behind you again
The sun is the same in a relative way
But you're older
Shorter of breath, and one day closer to death

Every year is getting shorter
Never seem to find the time
Plans that either come to naught
Or half a page of scribbled lines

Hanging on in quiet desperation
Is the English way
The time is gone, the song is over
Thought I'd something more to say

Home, home again

I like to be here when I can

When I come home cold and tired
It's good to warm my bones beside the fire

Far away, across the field
The tolling of the iron bell
Calls the faithful to their knees
To hear the softly spoken magic spells

1. https://en.wikipedia.org/wiki/Time_(Pink_Floyd_song)