No more what ifs: How to live more deliberately and stop postponing the things you want to do
This past weekend, I found myself doing what twenty-thousand other runners around the world were doing— excitedly watching a livestream of 370 runners make their way through the Western States 100 endurance race.
For those who aren't familiar, Western States is one of the oldest and most iconic 100-mile trail races in the world. Every year, runners spend months, or even years, preparing for the opportunity to stand on that starting line. You don’t find yourself on the start line of Western States by accident. The race is famously difficult to get into. It requires runners to dedicate themselves, usually for multiple years, by completing a 100-mile race every year in order to be eligible to enter the qualification and lottery process. Every runner on the Western States start already knows how to dream big and pursue a goal.
This year’s race was shaping up to be historic. With the deepest elite field ever assembled, and historically cool temperatures, there was a collective holding of breath, a sense that something special was about to happen. I believe there’s something deeply moving and fiercely inspiring about watching someone act on the belief they are capable of something extraordinary. Whether that’s the back of the packers, the everyday runners in the 50’s and beyond who have the audacity to dream they can finish, or the elite runners who have the audacity to believe they can break course records that have stood for years. Watching these runners attempt to pursue their dream felt a bit like watching performance art. It evoked deep emotions within me about living boldly, being the person you want to be, and what kind of life you want to look back on.
What kind of life do you want to look back on?
As a psychologist, I spend a lot of time talking with people who are struggling with a fear of failure, and the emotional sequalae that come with it— embarrassment, shame, self-doubt, rejection, or a sense of just not being good enough. I see so many of the individuals I work with struggling to begin at all, to take the first step toward something they want because the shadow of self-doubt is too large. I’ve also been there myself. Fear is powerful. The fear of not living up to expectations, the fear of the difficulties you anticipate encountering, or the fear of the sting of shame that comes with failure can quietly convince us not to begin at all.
But I want to talk about another fear I hear my clients vocalize— the fear of what if? The fear of quietly sleepwalking through one’s life, of living a life that doesn’t feel fulfilling, of finding oneself years from now wondering what if? It turns out most people desperately don’t want to postpone living, and yet that’s exactly what they do. We tell ourselves the timing isn’t right, that we’ll do the thing next year when things settle down, when we have more money, more time, more confidence, more certainty.
If you listen to interviews, read biographies, or talk to people who have achieved great feats in life, sport, or work, you may notice an interesting theme. Most of these successful, confident, and accomplished people openly share that they did not have confidence, certainty, or belief that they could achieve the feat they did until after it happened. Certainty and confidence were not prerequisites to their success. If the timing is never quite right, it certainly doesn’t arrive before action, and if confidence doesn’t proceed courage, then what are we waiting for?
In fact, research suggests that when people are asked to identify the most meaningful and fulfilling experiences of their lives, they almost always identify ones that required sacrifice, struggle, and a leap of faith – defined as belief that they could do something for the first time without a guarantee the outcome would be what they wanted. The magic is in being willing to begin even though you don’t know how it ends.
Change your relationship with regret
Regret is one of the feelings that lingers the longest. There are plenty of things we can do that we may regret— the thing we said to our partner, booking a hotel without reading the reviews, having that second or third slice of cake (ok, maybe no regrets there). However, research consistently shows that people tend to regret the things they didn't do more than the things they did— the conversation with never had with our parents, the business we never started, the hobby we convinced ourselves we were too old for, the trip we said no to. When researchers asked what emotion a cohort of adults feared more, failure or regret, a whopping 85% said that they feared regret more than failure. The researchers hypothesized that because humans have a bias for certainty, it was easier for people to make peace with failure than to make peace with the wondering and not knowing what could have been.
I was listening to a podcast I enjoy, and the hosts mentioned the following lyric from the song “Could Have Been Me” by The Struts. The lyric goes like this “"I want to taste love and pain. I want to feel pride and shame." Perhaps The Struts were capturing the same phenomenon the researchers above noticed: that the one thing people actually fear more than negative emotions like shame, pain, or a fear of failure is a life that doesn’t include the opposite end of the emotional spectrum – pride, hope, satisfaction, love, accomplishment. As a Psychologist, I find this lyric to contain a few other helpful truths. Of course, we cannot selectively experience only the comfortable emotions in life. Perhaps even more importantly, the goal isn’t to build a life where we eliminate difficult feelings. The goal is to become someone who can carry them.
What predicts lower levels of regret in older individuals? It’s not the job title they ascended to, the degree they earned, the accolades or rewards they received. It’s also not feeling like they did everything perfectly or that life turned out exactly as planned. The individuals over age 65 who reported the lowest levels of regret were the most likely to agree with the following statements “I cared deeply”, “I chose experiences over guarantees”, “I pursued something difficult”, and “I was willing to risk disappointment”.
When your life becomes a story, what do you hope it says?
I think it’s natural to view a Psychologist as someone who helps you get to the finish line. Perhaps though it’s also reasonable to view Psychologists as someone who helps get you to the starting line. My hope—for myself and for the people I have the privilege of working with—is that we can step toward the things that make us feel alive, and that one day, when we tell the story of how we spent our lives, it will make us smile.
If you’re ready to give yourself permission to do the thing, try one of the following reflections:
Define What "Fully Lived" Actually Means to You: One of the biggest mistakes we make is assuming we'll recognize a meaningful life when we get there. But if you don't intentionally define what matters most to you, it's surprisingly easy to spend years pursuing goals that were never really yours. Take a few quiet minutes this week and ask yourself, "If I looked back on this season of my life five years from now, what would I regret not making time for?" Your answer might be more adventures, deeper relationships, more creativity, better health, or simply being more present. Once you've identified what matters, choose one small action that moves you in that direction this week. A meaningful life isn't necessarily built through grand gestures as much as it is through making repeated choices that align with your values.
Stop Waiting for the Feeling and Start Collecting Evidence: Many of us unknowingly postpone living because we're waiting to feel ready. But confidence is almost always the result of action, not the prerequisite for it. Instead of asking yourself, "Do I feel ready?", try asking, "What's one small step the person I want to become would take today?" Then take it. Over time, those small moments become the evidence that you're capable of handling more than your fear would have you believe.