Use your midlife regrets to guide you to a better career (and life)
The only things one never regrets are one’s mistakes — Oscar Wilde
Moving through my early 40s, I’ve noticed how often regret comes up for me. It’s not something I talk a lot about, especially since American culture is notoriously averse to regret. We’re supposed to live a no-regrets life: either only do things we don’t regret, or simply get over regrets if we experience them. Just move on already!
Unfortunately, midlife regrets are an intrinsic part of the human condition. We all regret something we did or didn’t do in our younger years. In a futile struggle against time and entropy, we might get obsessed about coming up with ways to get back to that earlier stage of life. For people like myself who manage depression, anxiety or other mental health issues, regret can be sometimes paralyzing and debilitating.
Instead of fighting helplessly against it, what if we could reframe regret in a more constructive way to help us lead a better life and look to the future?
The Power of Regret
Daniel Pink’s latest book, The Power of Regret, takes a clear-eyed look at this most human of emotions. After reading through over 16,000 (solicited) regrets from his readers around the world, he classifies regrets into four categories.
1. I wish I had taken more risks.
I wish I had taken that job. I wish I had asked that person out. I wish I had traveled more.
All of these are examples of what Pink calls boldness regrets. According to him, this is the most common kind of regret that people express.
I can definitely attest to the truth of that statement. My biggest career regrets are all around staying too long in jobs I stagnated in because I was too scared to shoot for better things. I also missed out on prioritizing my own desires — traveling, taking vacations and so on because I wanted to be more responsible. Which leads to the second kind of regret that people express …
2. I wish I had been more responsible.
I wish I had worked harder in school. I wish I was more careful with my money. I wish I had bought a house back then.
These are examples of foundation regrets, where it’s actually about taking fewer risks, being more focused, committed and responsible around life goals.
I definitely have some of those. Even more than working harder, I wish I could have been much smarter about what I worked on, and more proactive about understanding how the academic and corporate world worked. I wish I had sought out mentorship and coaching sooner to fill my gaps. And yes, I wish I had done a better job with money, finances and pay negotiation.
3. I wish I had been a better person.
I wish I hadn’t been a bully to my classmates in high school. I wish I hadn’t made my friend uncomfortable. I wish I had stood up for my colleague in that meeting.
These are examples of moral regrets, where we wish we had been better people in a past moment. Pink says he was surprised by the sheer number of people who expressed these regrets and wished they could take back their actions.
I have a few instances where I might have made someone uncomfortable or not spoken up for someone when I should have. Overall, though, these regrets are fewer for me. Perhaps it means I’m a pretty good person, or perhaps I haven’t lived boldly enough to make too many of those moral mistakes (see regret #1).
4. I wish I had stayed more connected.
I wish I spent more time with my family. I wish I had talked to my friends more. I wish I told my parents I loved them before they passed.
Connection regrets are the ones we hear the most about when we read articles on people close to death. However, they can occur all through adult life.
I know I have a lot of those too. I wish I had more time with my father before he passed. I’ve always been introverted, and somewhat ‘out of sight, out of mind’, so I tend to lose touch with friends and family gradually and regret the distance later.
Reframing regret for a better career (and life)
Now that we know about the different kinds of regrets, what are we supposed to do with these?
Pink suggests thinking of these four kinds of regrets as the ‘photographic negative’ of a good life. Simply put, our regrets tell us what we’re missing, and what we need to be doing differently going forward towards our unique definition of happiness.
For example, if your biggest regret is around not taking risks, well, you gotta start taking those, even in a small way. The risks might not be the same today as they were 20 years ago, but taking these new risks will help mitigate that regret for the future.
As I started to hit midlife, I noticed a lot of regret around risk-taking (or the lack thereof) in my career. I regretted the number of times I followed a path simply because it was expected of me, and stayed on that path because of sunk costs.
Since then, I’ve been working on being much more connected with my inner desire and purpose, and using that as my compass to guide me along. Several years ago, I realized I was unfulfilled in my tech career and I followed my passion to pursue a career in photography.
As I tell my friends, since then, I’ve become a whole lot poorer and a whole lot happier.
Regret and Ambiguous Loss
Psychology professor Pauline Boss coined the term Ambiguous Loss as a way to describe the type of loss that results from someone (or something) being there and not there at the same time. For example, her book, The Myth of Closure, is co-written with poet Donna Carnes. Donna’s husband, world-famous computer scientist Jim Gray, went out sailing one day in 2007 in the San Francisco Bay and never came back.
When a person goes missing, they’re physically gone, but you don’t know for sure, so you hold on mentally to a version of them that’s alive. On the other hand, someone who’s addicted or has dementia can cause a similar feeling of ambiguous loss in the ones close to them, because they’re physically present but mentally gone.
I believe that ambiguous loss is a close cousin of regret. When I regret doing or not doing certain things, I also find myself grieving the loss of the person I might have become or the life I might have had as a result. It’s a classic example of ambiguous loss — a version of me is here, but I’m grieving the loss of a different version of me at the same time.
According to Prof. Boss, we try to deal with grief in American culture in the same way that we deal with regret. We either attempt to medicate it away, or try to create a quick, simple, linear process. Just go through the five stages of grief and you’ll reach closure! In reality, grief is not linear, closure is a myth and the five stages of grief were originally meant for people who were terminally ill, not for those mourning them. We can manage grief, but we can’t eliminate it completely, and there will be times when it keeps returning to haunt us.
So what helps with ambiguous loss? Getting comfortable with the idea of ambiguity is one strategy. We need to accept that we might grieve and find happiness in different ways at the same time.
Finding new meaning and new hope are two other important strategies to deal with loss. This is where the idea of using our regrets constructively comes into play. Instead of trying to recreate the old hope — the disappeared person will come back, or we can live that younger life again — we have to find new things to look forward to. We have to show ourselves that we have learned from our regrets and are using that to inch closer to our definition of a good life. That is what makes those regrets meaningful, and helps us manage that sense of loss.
Takeaways
- Midlife regrets are an inevitable part of the human condition, along with a sense of grief and loss for what might have been.
- It’s not practical or desirable to suppress these regrets or simply try to get past them. But it is possible to reframe them and move on by finding new meaning from them.
- Our regrets are a ‘photographic negative’ of what a good life means for each of us.
- We can use our regrets to guide our future behavior by doing more of the opposite. That way, we bring meaning to our regrets and our future lives.
A little about me
I went from being a data scientist in San Francisco in my late 30s, to a professional photographer in NYC in my early 40s. I help entrepreneurs, coaches, authors and speakers to convey their own transformational story and work through genuine, powerful photos. Check out my work at Series A Photography.
