Nomad & Roots

On the Demons You Know

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There are two basic types of regret:
  1. Regretting not doing something
  2. Regretting doing something
The first type of regret, the regrets that come from “what if” – what if I had said how I felt, what if I had taken a chance on that business idea, what if I had traveled more, what if I had said I was sorry – these are the regrets that people are most haunted by. These are the regrets that people spend their entire life pondering, wondering how things might be if they had stepped outside of their comfort zone for something they wanted. These regrets leave people with lives that feel incomplete, unfulfilled, full of wasted potential.
The second type, regretting making an effort, well, I’d be lying if I said that these regrets didn’t exist, but they are far less common. When you speak to people who have taken a chance in pursuing something that mattered to them, their stories are more often about empowerment, about the lessons they learned, about how they grew as a person – even when that chance didn’t pan out exactly the way they’d planned. When we take a risk to follow our dreams, we know the outcome, and even when the outcome wasn’t what we had hoped, and we don’t have to live with the “what ifs”.
Despite the tendency for people to face stronger regret for NOT doing something, most people live their lives making decisions out of fear of change. We tell ourselves that it’s better the demon we know. We tell ourselves that what we have now is pretty good, it’s something at least, better not to risk any of it for something great. We stay in jobs we hate for fear of not finding something better, we stay in relationships that don’t serve us for fear of being alone, we hide our gifts and creative passions from the world for fear of being judged, or worse, ignored. We tell ourselves that if we just stick it out a little longer something will change, some magical solution will appear that requires no risk, no deviating from our comfort zone. And if it doesn’t, well, perhaps we’ll pursue the life we really want in six months, six years, some distant future that never seems to come.
So why do we do this? Why does the fear of regretting a change consistently outweigh the fear of missing out on our lives? We cling to the demons we know because we think we have time. We tell ourselves that we’ll have time to do the things we really want to do later, so it’s not really worth a potentially scary change now. Later is seductive, it tells us we can have it both ways, lets us cling to the hope that fate will intervene so we don’t have to do the scary thing ourselves. The problem is that if we rely on later too long, later never comes. This is how so many people end up with the most painful regret, the regret of never going after your dreams.
What are you telling yourself “later” about? What steps are you going to take to make sure later doesn’t turn into regret?


Mindset coach and creative, currently rooted in Washington, DC.