Ten years ago I moved to San Francisco with everything I owned packed up in a Honda Civic. The value of my student loan debt far outweighed the value of my material possessions and if I didn’t find a job quickly, I’d have to pawn my shoe collection.

I liked my shoes, so I hustled.

A month later I had two VERY different job offers, each offering a unique life: high tech and fashion retail. Which to choose?! Choosing fashion was the first of 200 other forks in the road where I blindly picked one direction and sprinted ahead. I wish I could say I never looked back. But I’ve looked back regretfully many times, wistfully thinking what my life could have been had I chosen differently. Richer? Better? Happier?

But what if it never would have been at all?

Regretfully second guessing is a dangerous game, speculative at best. It isn’t accurate and it paralyzes us from moving forward. So how do we stop regrets from overtaking us?  How can we become happy with the choices we’ve made?

The Job that Wasn’t

In San Francisco, many of us dwell on that one startup offer we didn’t take.  We wistfully think of that pregnant chunk of equity that would give birth to trillions of dollars. With its success, we would have instant credibility to write thought provoking articles on cat memes that everyone would pay attention to and tweet across the interwebs.  We’d go on to write books and speak and conferences with Bono. Why, oh why, did we turn it down? Were we dubious of the value proposition? Or did we fear the grueling hours wouldn’t allow us to be creative?  And I sigh, thinking how creative I could have been decorating my bedroom with million dollar bills.

Money, fancy title, or other opportunity aside, we don’t really know what would have happened had we taken a different job offer. Maybe we would have had a terrible boss and had our self esteem taken away until we quit. Or worse, been a spreadsheet slave, and missed out on major life moments. If I had a “normal” job in 2010 I never would have taken a road trip across country to document stories. This included writing down my Granny’s story before she passed away. Family equity > tech equity.

It’s not about a job or salary or title but rather, what we contribute to life. The right “job” should give you the right “life”. After all, I finally landed at IDEO (aka “the Job That Was”) not because of my work resume, but because they liked I took time to write about people. They still encourage me to do this.

 The One That Got Away

A good friend of mine went to high school with the co-founder of WhatsApp.  He asked her to Prom, and she turned him down.  After they sold the company for $19 billion dollars, she told all her girlfriends—“Let that be a cautionary tale to all of you.  Never let the quiet geek get away.”

She meant this as a joke, of course, but we all have one we think ‘got away.’  You know, that one young passionate love that devastatingly ended? We forget why it ended and romanticize the memories; they are much funnier, cuter, and smarter than they actually were. We think, What if THEY were indeed our soul mate?! Then on a lonely Friday night, fueled with Downtown Abby reruns, we start stalking them on Facebook and think reconnecting is a really good idea.


It’s kind of like taking the remnants of your amazing French Laundry dinner, putting it in a tupperware container, and then trying to eat it ten years later (with freezer burn) in your tiny apartment and hope it’s the same experience.

Keep the great memories –seal them in a jar and never open it again. Our romanticized recollections are 50% better than our real past together and 100% better than it would be in the future. I know there’s all those one-off Readers Digest type reconnection stories, but generally when something breaks, there is a reason why. Why salvage something broken when you can start fresh and build something new? (i.e. Go Tinder!)

To Travel or Not to Travel?

Most people think they didn’t travel enough. I, on the other hand, worry I traveled TOO MUCH.  When I sit at tables with San Francisco overachievers, I feel judged, as if I had spent the last 10 years running through fields of international flowers like a bad Tampax Commercial while everyone else was slaving away building companies and getting married. Not me.

Six years ago, I broke up with my boyfriend because I needed to travel the world for 6 months and he didn’t want to come with me.  “I can’t just do that,” he said. “I have a real job.”  I took this as a personal insult to my life and decided that this, in addition to his inability to ski, doomed us. He’s now responsibly married with a career, house and child and I’m still living like a character in a subtitled film. However, my travel did teach me some great insults in Swahili like “Kuma Kubwa chupi ndogo”  (Your vagina is so big your underwear doesn’t fit you).  Ha-how many responsible people can say that?!

As I returned from my 6 month world trip I regrouped my questionable career. Not long afterward, I decided to go with my friends to Brazil during an important client meeting.  I really meant to get on the conference call and chime in remotely, but I messed up the time zones and was surfing as the executive sat on an empty phone line. That relationship went about as far as my romantic one. (I am much better at calculating time zones now).

Three years later, questionable career intact, I met a prospective client at Fashion Week in NYC. The CEO asked me if I could help reposition one of their brands. I asked if he could wait for 3 months because I had to finish my road trip across the United States and further my blog with 38 followers.

So yes, I have spent time regretting irresponsible travel decisions. However, when regret gets the better of me, I play the  “If I die tomorrow” game.  If I die tomorrow and have 20 minutes to reflect on my life, I am grateful that it’s not filled with memories of meeting rooms and power points and boring boyfriends with their picket fence houses that keep me inside. It is filled with oceans and mountains, and people laughing in different languages. Some of these experiences gave me lifelong friends.  Some posts on my blog are now read by thousands of people. This means much more to me than a fashion gig.

Are the Wrong Choices the RIGHT Choices?

Someone once told me, “We will never know if we made the right choice.  But if we are happy, at least we didn’t make the wrong one.”

However, I think there is more to this. I think that if we make decisions that fuel who we are and what we believe in, it will be hard to ever have regret.

A great article by Elle Luna (an ex IDEOer) writes about the crossroads of shoulds and musts and the need to accept who we are. It’s hard to have regrets if we keep true to ourselves.

She writes,

“Should is how others want us to show up in the world — how we’re supposed to think, what we ought to say, what we should or shouldn’t do. When we choose Should the journey is smooth, the risk is small.

Must is who we are, what we believe, and what we do when we are alone with our truest, most authentic self……Must is what happens when we stop conforming to other people’s ideals and start connecting to our own. Because when we choose Must, we are no longer looking for inspiration out there. Instead, we are listening to our calling from within, from some luminous, mysterious place.”

Elle goes on to lists many examples of people like the Airbnb Founders, Van Gough, and John Grisham, that at one point seemed like failures (making the wrong choices) but ultimately achieved enormous success.

I’m far too free spirited for a normal linear career (sorry Lean In advocates–you know I have issues with you) and a normal linear relationship. After years of second guessing and woefully comparing myself to my smug executive married friends, I’ve FINALLY accepted that in myself and am happy.

If you can accept yourself, then regrets dissipates. We become more confident in the path we choose and more optimistic about how our past decisions (right or wrong) are a crucial part of our fabric that will take us forward in life.

When we skipped meetings…

“I never regret anything. Because every little detail of your life is what made you into who you are in the end.” -Drew Barrymore

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