Writing, Regret, and the Quiet Work of Redefining Success

Last week, I went into a virtual writing retreat with high hopes for what I would produce, but what I got out of it was far more meaningful than I could have imagined. I signed up for the retreat with Tara Mohr – a coach and author I have long admired – without a clear goal aside from enhancing my writing skills. I thought I’d be writing a detailed travel guide based on our summer family vacation in Japan, and stuck with this plan at first, but Tara’s inspiring writing prompts gave me the leeway to drop my achiever tendencies and write instead about topics that emerged in the moment. 

I choose to write about questions that have been swirling in my mind for a while, especially as my corporate career feels more and more like a thing of the past. I find my identity transforming into something yet undefined and I grapple with a mix of pride in my past work and a pang of regret. Was I successful, and if so, am I still? If this is the end of a big fat volume of my career, did I reach my full potential during that time? 

The next writing prompt asks: If I were being brave(r), what else would I say about this?

I go a little deeper: am I happy with how things have turned out for me? Is it possible that I could have been more successful in my career, earning fancier job titles and higher pay? These are uncomfortable thoughts because they reveal my insecurities and I don’t know what I may uncover, but I decide to use the process of writing to examine them. 

When I took mental health leave for burnout, the silver lining was learning to have self-esteem, believing that I am both capable and worthy. It was a profoundly emotional moment for me that stirred up conflicting feelings: until then, I simply could not fathom how or why I would value myself for who I am and not what I do. Learning to love myself and treat myself with the same compassion that I felt for anyone else but me freed me from the heavy feelings of guilt, imposter syndrome, and self-criticism that verged on self-loathing. And yet, I felt a twinge of embarrassment and frustration that it took me until the ripe old age of 50 to reach this point. 

Why did it take me so f**king long? Why did it take me half a lifetime or more to finally get it? Is the purpose of life to take a long, painful journey with the goal of attaining enlightenment, peace, freedom, and liberty? Is that why we’re here on earth?

My frustration exposes a longstanding belief I have about myself: I’m a late bloomer when it comes to confidence, leadership, and strategic thinking. I must be a timid, naive, and simplistic person. As I’m writing, I become curious: what’s wrong with that? To me, it means that I missed an opportunity – I could have lived more happily in my 20s, 30s, and 40s, without carrying the burden of insecurity and self-doubt. And when I get even more honest and vulnerable about this, I feel I probably could have been more successful. 

What are some of the paradoxes at play here?

My self-judging voice says I should have been more successful, that I should have advanced more quickly  in my career and earned more money. Maybe I would have been part of a big IPO or be rewarded millions of dollars in stock grants or bonuses and would be set for life financially now.

But this is also true: I don’t actually define my own success by money or status. I’m grateful for the life that I have right now and wouldn’t want anything to be different. 

While in some moments I feel envy, regret, and inadequacy as I look back on my career, it’s because I know that I am capable and high-achieving, and have the ability to do bigger and better things. But to what end? What’s worth the trade-off of giving up what I value most in my life right now?

What is my inner mentor perspective about this?

My voice of wisdom asks me what I think my missed opportunity might be. What have I not earned or accomplished that I truly long for? The most obvious answer is financial independence – not having to worry about earning income for the rest of my life. But who would I be if my choices had been guided by prioritizing financial gain over everything else? 

Would I have let myself take time for yoga teacher training, coaching certification and mental health leave? Would I still have quit my job without having the next one lined up? What jobs would I have chosen along the way? Would I have met the love of my life? Would I have been more stressed out? If I had strong self-esteem back then, would I have been able to avoid all that angst? 

Reading Careless People: A Cautionary Tale of Power, Greed, and Lost Idealism this week made me wonder if power and wealth would have turned me into a different person. My career allowed me to preserve my humanity and make decisions without tuning out the human element. If it turns out that I’m at the end of my professional career, can I be proud of how I’ve handled myself?

My inner mentor asks, what good comes from allowing the feeling of regret to remain? Who does it benefit? Certainly not me. It doesn’t lead me to different decisions. This awareness gives me the freedom to let go of any judgment and regret that do not serve me.

On the last day of the writing retreat, Tara shares her Art-Making Poem, and the idea of writing as “vessel for your thoughts” resonates: for me, the joy of writing is taking the swirl inside my head and allowing it to take shape into something coherent. It’s creating the space and being my own loving witness. And then just maybe, it is something I want to share with someone else. 

I know that I’m not alone in my thinking; I have heard from other people who feel like they are behind in life. If you ever feel this way, I invite you to reflect on what could have been. What alternative choices would have led you down another life path? What would you have gained that you don’t have how, and what would you be giving up from your current reality? I have a feeling most of us would not want to trade our lives as we know them. 

If you’re nodding your head in agreement, you are on your way to choosing acceptance.

But if you still have regret or resentment that you’re not where you want to be in life, please don’t wallow in misery forever. Get curious – what does that feeling tell you? How can it influence the actions you take next? Perhaps this lingering desire will be just the spark you need to make a small change, to try something new or different, or even to revisit a past failure and give it another shot.

If you’re interested in going deeper on this topic, check out The Power of Regret: How Looking Backward Moves Us Forward by Daniel H. Pink. It’s been sitting on my bookshelf for years and while I fully admit I haven’t read the book yet, there’s an endorsement by Brené Brown on the back cover, so that’s good enough for me. Seriously. I promise to read it soon and report back if I was wrong.