Catching Up Doesn’t Have To Suck


​One of the hardest things for me to do is playing catch up.

This doesn’t refer to something new that I am curious about or want to become good atit’s about catching up on things that I used to be good at or something I have lost momentum on. I have always felt a sufficient drive and enthusiasm in making the time to learn, practice, and execute something new.  It’s been much easier to stay in the mindset of, this isn’t something I want to be good at any more (but not always more on that later). 

This tweet storm titled Some loose thoughts on ego, fear and losers” helped me realize the parallels between my attitude and the Aesop’s fable, The Fox and the Grapes.” Something that seems unattainable has now been termed sour grapes”; hence, it’s unworthy of my time and effort. This is a good rationalization, but it’s a blanket protecting me from my own fears between where I am and my expectation of where I want to be. 

Much of this past week, I have tried to recollect times when I have succumbed to this behavior and why I didn’t go back to the original activity. There have been many reasons:  

  • Inertia: The path of least resistance is to do nothing. Depending on the activity, the amount of activation energy needed to get started again might be variable, but it’s certainly a blocker. 
  • Fear: I used to be good, but if people find out I am not good anymore…disaster.
  • Regret: Imagining how much progress could’ve been made in the time that passed. The present hasn’t lived up to the future you had expected in the past — you regret how time was spent. 
  • Competition: People who I consider my peers are further ahead on some arbitrary scale. They’re ahead and I need to catch up. 
  • Prioritization: This is no longer a priority for me, so I don’t need to go back. Funnily enough, this is a sword that cuts both ways: it’s a weak excuse to not go back or it’s an incredibly powerful tool to eliminate non-critical activities. 

Having become aware of these reasons, I’m working to spend time improving upon my behaviors. Here are a few ways that have helped me over the years to get back into things and make catching up suck less: 

  • 10 Minutes: Start with doing the activity for just 10 minutes and make sure to accomplish something small. This will help build momentum and help evaluate the path forward in a more objective fashion. 

    • Eg. Doing this with writing and publishing it. Just 10 minutes a day has been very helpful in making me comfortable with my own writing again. You’ll be seeing a lot more content here.  Eventually, the activity will last longer than 10 minutes. 
  • Humility: The fear of fear is usually the biggest blocker usually. Be okay asking for help with simple things, and find people you can feel comfortable being vulnerable with and can help you improve. 

    • Eg. Math/Data Science — I am taking an online course to  improve as I haven’t really done any math or Data Science in two years…learning the basics which I was so familiar with is a bit painful, but there isn’t a path forward without it. 
  • Rubric Yourself: Write out goals and milestones that you want to measure yourself against as opposed to comparing against the success/momentum of other people. Be realistic and unrealistic at the same time. 
  • Use Time Gaps as a Tool: Asking yourself to take a break from something you regularly like doing can help evaluate its priority and value. The activities that have I always caught up after a break remind me of my priorities. 

    • Eg. Photography — I didn’t take pictures for most of this year. I recently got my camera back and have made a few hours every weekend getting comfortable with my gear and taking pictures again.

There are 3 activities that I’ve been applying the above to. will have more to share in the coming months on how effective the above has been for me and whether it’s been able to help me making catching up easier.