With Regrets

Midway through college, two of my closest friends took a two-week road trip through the South. It was somewhere in Tennessee that they got matching wrist tattoos: “No Regrets” scrawled in fancy, black script.

I’m glad I didn’t take that trip because there’s no doubt I also would have gotten the tattoo and, ironically enough, I think I’d regret it today. Instead I have a regret that’s a little more serious: I haven’t spoken to either of those girls in years.

Friendships, even the best of them, can be fickle.


I have plenty of other regrets, of course, as most of us do. One of my biggest is staying in New York long after I had soured on the place. I should have cut my losses and moved on after a few good years. Instead I kept doubling down: I started a new job; Found a new apartment; Fired up an online dating account. I was looking for every reason to stay when the only thing that would make me happy was to leave.

I knew that, but I still I kept trying “one last thing” in case it made a difference. I was bored, so I found a hobby. The city was suffocating, so I took more vacations. I needed an escape from work, so I installed an aquarium in my office. That last one almost worked in that our CFO offered to fire me over it.

But, as regrets go, I guess not leaving New York soon enough isn’t so bad. It certainly beats not leaving at all. If I’m going to look back on wasted time, I’d prefer it’s measured in years as opposed to decades.


I had my reasons for not leaving New York – namely that I had already done it once before and it didn’t go so hot. In 2010, I joined the Canadian version of the Peace Corps and took a position as a marketing specialist for an HIV/AIDS organization in Nigeria. I was 27 at the time and was barely competent as a marketer, let alone as a  development worker specializing in health services in West Africa. But someone with questionable judgment thought I was up for it and I lacked the good sense to say no, so off I went to Abuja to give it a go.

My contract was for five months, but I only lasted about three, during which I nearly lost a hand to a metal ceiling fan, sat idly by while the third floor of the building I worked in caught on fire and accidentally ate a grilled rat. What can I say, I’ve always been efficient.

At the end of every day, after I walked the three miles back to my apartment, ate a can of chick peas for dinner, and took a bucket shower, I said to myself: “After this, everything is going to seem so easy.”

And it was. When I returned to New York and settled back into my usual routine of working, socializing and exercising, life was pretty simple. But an easy life is not necessarily a happy life. A few years passed and I got bored again. Then I got restless. I wanted to leave, but I didn’t dare try because I didn’t want to fail again just 90 days in. And so I got depressed.

Speaking from experience, here is a list of things that will not help you overcome crippling boredom:

  1. Bangra classes
  2. A collection of designer handbags
  3. Rosé
  4. A Nespresso machine
  5. Netflix
  6. Keratin treatments
  7. A raise
  8. Training for a triathlon
  9. A desktop aquarium

Here is a list of things that might:

  1. Doing whatever it is you are desperately trying to talk yourself out of


Before I made the decision to quit my job and leave New York for the second time, I contacted my doctor, my financial planner and my mentor. I wanted to know if I was ready – healthy, financially stable, professionally secure – to make a move. I’ve since learned that this type of questioning is called “seeking approval.” It’s what people do when they want permission to make a like change.

The thing is, no one can approve that kind of choice. At best, the people closest to you will encourage you to shake things up and comfort you when you lose your nerve. The rest of them – your financial advisor, your landlord, your dentist – they’ll just tell you what you already know: you saved a lot last year; your lease renewal date is coming up; your flossing habits suck.

They can’t – and won’t – make the decision for you. Gather all the evidence you want, but only you can follow through.


This past weekend, while I was at home in Philadelphia, I ran into a few acquaintances at my sister-in-law’s birthday party. Aside from complaining about my train wreck of a haircut, I spent a lot of time confirming that life after New York is as good as it looks online. I’m happier than I’ve ever been – probably because I finally decided to focus on the things I want to do, as opposed to the things I thought I should do.

My brother’s friend, Scott, a career coach, backed me up. According to him, people who make a big life change usually don’t regret it. They actually end up being happier and more satisfied. I didn’t ask to see the numbers on that, but I believe him because I’m living proof.

Since we’re on the subject, I’ll add another generalization I’ve heard a time or two: When people think about regret later in life, they don’t usually focus on the things they did, but what they didn’t do. For example, I might have failed in Nigeria, but I don’t regret going. That logic is what finally convinced me to pack my bags again.

All this is to say that if you’re thinking about making a big change… if you’ve been thinking about it for a long time… if it’s the only thing you’ve been thinking about… if you can imagine how your life would be after you make it… if you can’t imagine being happy any other way… then I totally can’t tell you what to do next. I can, however, lend you a beautiful little fish tank should you interested in trying one last thing.

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My brother’s career coach friend shared plenty of other helpful advice from his years working with people who want to make a change. Next week, I’ll be posting a full write up of how he responds to some of the more common concerns, excuses and fears that people have when evaluating change. Stay tuned! And in the meantime, you can visit his website here

  1. It’s that point you hit when you say “dammit, I’m going in now” and never look back. I’ve felt that, and it’s almost always a no-regret kinda thing.

    and look at it this way; all those other things you did that just missed or were howling mistakes, taught you stuff. They grew you up a bit, and this time you were ready to leave.
    My dad always said, you don’t learn from what you do right, you learn from what you did wrong. That’s when you sit down and think, “that was NOT a good idea. Why wasn’t it?”

    • i have so many “howling mistakes”. god. i love that. I’m stealing that too! (you’re the person who coined the term “weasel words”, no?) regardless – thanks for reading. glad you jump in with both feet too!

  2. I asked for approval to work remote fulltime last night. I am terrified…relieved…and waiting a reply. Thank you for sharing your travels. They are so helpful in reminding me that I can do this.

  3. I love living vicariously through you! Your way of life is endlessly fascinating to me, probably because it’s so different from mine. Plus, you write for a living – it’s THE DREAM.
    Doing the scary thing may be hard, but it’s harder NOT doing it. I completely agree with you: The things we didn’t do will haunt us later!
    I’m very much looking forward to your upcoming post about evaluating change!

    • Amen. I’m living vicariously through you too, don’t you worry. Maybe one day I’ll have a farm… or at least a farmhouse. Until then… keep it making it look good. xx

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