Answering the Question: Don't Look Back in Anger
Turning our past choices into bricks and mortar in an effort to build our future. PLUS a word from our readers.
You know, I owe you an apology. I’m a really mean guy. Look at me, making you reflect on the past like this. Who do I think I am? Awful. Terrible. I deserve all the shade you want to throw my way.
…
Is this me talking to you or the man in the mirror? Who knows. Regardless, this week’s exploration brought me face-to-face with a plethora of past choices I haven’t unpacked for a bit. If it did for you too…sorry, not actually sorry. That’s the point!
So, where were we?
How have my mistakes helped me enjoy where I am now?
Answering The Question: Bricks and Mortar
“What do you regret from the last decade?”
“…”
“Come on, there has to be something!”
“Not that comes to mind! Maybe that I wish I started creating content earlier? But I have no idea what it would have been about so, I guess, yea, I guess I don’t know…”
“Okay but that’s something!”
“Yea, but, that feels like I’m telling you something just to say something. I just feel like all the choices I made in life have brought me to this point. So I don’t really regret anything, because if even one thing was different, I don’t think I’d be where I am right now, and I like where I am right now.”
Like most people, it was at a Greek restaurant in Tampa, Florida where I received the gift of unlocking deeper insight into my own psyche, thanks to this dinner table conversation. I mean, isn’t that where Freud got his start?
It has been ~18 months since that dinner and in the time since I’ve found the topic of regret often not far from my mind. As someone with anxiety I’m right at home running it back on my past faux pas, mistakes, embarrassments, and bad decisions. We love a greatest hits of the worst hits and certainly my discography rivals that of Frank Zappa’s.
Of course, the question I had to ask myself was whether I was protecting myself from the emotional elements of regret and disappointment by breezily deciding that I had none. A deft act of avoidance.
Pages and pages of journaling later, I’ve come to the conclusion that I wasn’t. See, these past choices are the Bricks and Mortar of my life, and I love the house they have come together to build.
Bricks
In my anecdotal experience, when asked to name a regret, most people tend to identify the “big ones.” Things like college attended, career choice, city lived in, partnerships made (or avoided). These are the choices that leave us wondering how different life could be, the What-Ifs.
I like to call these moments our Bricks.
Bricks are the big decisions that typically have lifelong ramifications, like the ones I just identified (where/whether to go to university, whether to have kids, which job to take). All of these are decisions that will define who you become, who you will know, the resources you have, and so much more. They help create You. If a single brick was to disappear, your home might not crumble, but it will look different. There will certainly be a noticeable void, a change in appearance.
Are there moments in life I’ve regretted the Bricks I’ve laid down? Hell yeah! Throughout my four years at Georgetown University I daydreamed about what life would have been like had I started my college career elsewhere. The decade or so that my partners and I ran Digital Natives Group was accompanied by a decade or so of second-guessing my career path and decision to embark on that venture.
Actually, let me run with that example for a second.
Multiple times throughout our agency lifespan, and even in the years since, I’ve told myself starting that business was an incredible misstep for myriad reasons. I stayed up several nights crying over the decision, wishing my life hadn’t been so defined by the choice, wishing I had done something else. There were opportunities missed, relationships impacted, and serious financial repercussions.
But to sit here and tell you I regret that choice, that I wish I had done something, everything, differently would be to tell you I am unsatisfied with the person I am today. And the thing is, I’m not. Am I a whole and fully realized person? Absolutely not. I’m always a work in progress. But to take away the experience I had with Digital Natives Group and substitute in a different career arc would take away not only all the positives it brought to my life, but also all the challenges I faced, overcame, and learned from. Would I have become the manager I am? Would I have had the chance to travel the world the way I do? Would I have the same perspectives? Would I have met the same people?
So do I regret starting the business? Going to Georgetown? Any of the people I’ve dated? The cities I’ve lived in?
No, because these choices made me who I am. These are my Bricks.
There’s something people tend to forget about Brick decisions though: you can make them at any time. While you can’t remove the old ones, you can always add the new. In fact, the more you add, the better. The more Bricks, the…higher and stronger your creation becomes, the more realized you become (bear with me, like me this bricks/mortar metaphor is a work in progress).
And we’ve all heard the stories of folks doing this before. The person who blows up their marriage to find themselves and travel the world. The 50 year-old who forgoes retirement to pursue an unrealized career in medicine. The couple who moves from Boston to Belize simply to try living abroad.
But to hold those Bricks in place, you need Mortar.
Mortar
Around each of our big decisions are the compounding choices we make that give color to each experience. Do I take Intro to Algebra or Intro to Geometry as my math elective? Do I join this affinity group at work or not? Do I accept the wedding invitation or speaking gig?
In my own life, this means looking back and finding myself saying things like:
I wish we broke up earlier.
I wish I had spoken up, and spoken differently.
I shouldn’t have skipped that event.
These are not the Whats of my decisions (what college, which partner, which career) but the Hows: how did I curate my college experience, how did we handle our break-up, how do I manage my time, etc.
I wish I didn’t. If only I could have. If I could do it all again…
If the big choices are the Bricks that make up the foundation of our identity, these choices, the Mortar, are the material that hold them together and allow us to build the life we want. When we look back on them, we learn lessons about ourselves and our needs that can inform our decision-making in the future. Listen closely to your pain, your regrets, and you’ll learn something about how to make better choices in your future. These are the growth moments, should you choose to accept them. Your chance to lead a more authentic life.
What would that look like for me? Consider:
I wish we broke up earlier. Translation: I wish I wasn’t so afraid to honor my feelings.
I wish I had spoken up. Translation: I wish had been less afraid of the way people would perceive me for speaking my truth.
I shouldn’t have skipped that event. Translation: I wish I better prioritized my time and energy.
To expand on this, take failed relationships (Bricks). With the benefit of time (it heals all wounds, ya know?), I can say there’s not a single romantic entanglement (casual dating, situationship, formal partnership) I truly regret. Each one taught me something about myself, the person I want to be with, and the partnership I want to make. Each also pushed me to evolve as an individual.
When reflecting on those relationships though, I did begin to see where I could identify the regrets, and it’s around the Mortar. I wish I hadn’t accepted a certain kind of treatment. I wish I had left sooner. I wish I had responded to something differently. While those past choices are unchangeable, I can remember what I wish I had done and use that to inform and shape the future.
As an abstract example, consider someone saying they wish they had invested in Peloton and Zoom at the start of March 2020, implying the wish they could have experienced a cash windfall from the subsequent stock surges. What if we asked that person to explore why this is a regret? Seemingly, they wish they had more money (who doesn’t). That’s great, but money is not the end, it’s the means. What would having more money enable you to do? Quit your job? Do some philanthropy? Exploring and identifying that second-degree desire can turn that regret into an insight about how you need to live your future life, and you don’t need to change the past to do it.
In Sum
While my thinking has evolved since the conversation I mentioned that kicked this answer off, my root belief stays the same: I see my past missteps, but now I see them for their gifts.
Could I fantasize about what might have been? Sure. But I’d rather focus on what can be. My choices made me, and for that I thank my past self, because my current self is thirty(-three) and thriving, and making better and better choices thanks to my mistakes, and the mistakes I’ll continue to make.
Answering the Question: Our Readers Speak
Happy to say we have some reflections from some of our readers this week, and I feel privileged to be able to share some of what they had to say with all of you. (And let’s keep the conversation going. Is there a decision you regret? Let’s talk about it in the comments. And shout-out to Camber for her contribution this week!)
A reader response from this week:
i think about this often. i've made a lot of "mistakes" in my life. some big, some little. some were just silly mistakes most people make...there is one saying that always sort of guides me when i start to question what my life would look like if i hadn't made so many mistakes or faced so many obstacles: lo que está pa ti nadie te lo quita.
basically, what's meant for you is meant for you and no one can take it away.
Thank you so much for sharing, and as always if you ever want to share something just drop me an email or a DM with your story.
Something For The Weekend
Candles are a huge part of my self-care and journaling journey. I have my desk candle, my table candle, my kitchen candle, my bathroom candle, and then some.
After some reading I’ve tried to stay away from low-quality candles that may be rich in dangerous chemicals and stick with higher-quality ones. The best I’ve found so far come from Soul Food Candle Co., a Black, LatinX🇵🇷, & Queer-owned business based in LA. The scents last until the bottom of the jar, and when they’re done they make great planters for succulents.
Gonna need you to check them out and order ASAP.
See you Sunday friends!
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