To All The Past “Me”s

To me, age 8: Don’t listen to her, she doesn’t actually know who you are or who you will want to be. Find ways around all of the arbitrary rules you get caught up in to do the things you want to do. Trust me, they exist. I know, I know — rules are there for a reason, you’ve got to follow them. But honestly… you usually don’t. It’s easier to ask for forgiveness than permission.

To me, age 11: You won’t even remember who these people are. Start ignoring others’ opinions sooner. 95% of the people at any point in your life will have zero impact on it beyond what you allow them to have. Most of them are perpetually negative, come from a culture of defeatism, and will never even step foot outside of this town to see what else the world might hold for them.

To me, age 14: Stop listening to this kid. Wait until you see what he’s like as an adult. It’s all just… yikes. I mean… really bad. This is the type of friend who will drag you into their own personal hell and try to convince you that you caused their problems for them. Find better friends. This one is a raging tire fire.

To me, age 16: She is actually not worth your time and emotional well-being. I can’t stress this enough to you.

To me, age 17: She actually is worth your time, and you’re going to throw it away for nothing, and for reasons that you can’t even put into words right now. I can’t stress how huge of an asshole you are about to be. You should strongly reconsider your choices.

To me, age 19: Is this something you will enjoy doing forever? Are you sure you won’t be tired of being “the computer guy” to everyone that you know, except that what you actually do is create software? Are you sure you’re ready for the layoffs in your Rust Belt town? Are you ready to get screwed out of money that would be too little of a reward to go to court over? Are you sure you shouldn’t keep going with the artsy-fartsy creative stuff — you know, the stuff you’re really good at right now? Do you even know that this town doesn’t pay engineers well? Don’t listen to your career counselor, that man is a certified moron.

To me, age 21: You think this is cool now? Well, just wait until you’re 23!

To me, age 23: Yeah, you look really cool as your friends watch you get taken down to the station, don’t you? Have fun walking a few miles to work for the next few months during winter in a town with no public transit. Good job, idiot.

To me, age 24: Try harder. You actually will miss this one day, but not for reasons you understand yet. You will come back haunted in a way you can’t understand yet — maybe you never will. You will be shaken with revelations. Pay even closer attention and absorb even more details. Prepare for a type of betrayal and sadness you don’t even know possible. Read more philosophy than the limited set of authors you are comfortable with. Start writing now, not in the future. It will help you crystallize ideas into more meaningful and correct forms.

To me, age 26: Once again, you won’t talk to these people in the future. Find better friends. I know they seem like they have your interests in mind, but really pay attention to how they behave. See if you can spot which one is actually a Pretty Terrible Human. Nope, not him. Not her, either. Yeah, that’s him. That’s our man. Cut him out right now, because he is toxic, and you have too much history together to see it right now.

To me, age 27: This is a chance that you shouldn’t blow. In the reality I live in, however, you completely blow it. I mean, spectacularly — you really should get an award or something. Consider all the different ways you might blow it here, and then just do the exact opposite of that. Trust me on this one. I know you are angry about a lot of things, but this is not the time nor the place. While you’ve come this far without too many regrets, you will regret this. Your complete lack of humility will be your undoing.

To me, age 29: This job sucks. These people suck. You know this, however, and you leave within two months. Good job. You’re getting closer. To what, neither you nor I know, but it’s… closer. Authentic behavior creates authenticity.

To me, age 30: This thing you’re working towards won’t be worth what you think it will be worth in the future. Either change up your focus or double down, but don’t just think “this will be enough,” because it won’t be. Please stop thinking about money.

To me, age 31: You know you’re only dating her because so many of your friends wanted you two to get together. It was a coordinated effort among all of them. You’re a new couple in the friend group now! But you know you don’t really love her. You feel like you’re letting so many people down, not the least of whom is her. You end it between you two sooner rather than later, though. I can at least respect that. Maybe you’re learning.

To me, age 32: Yes, that is another pang of regret. This time, the source is atrophied creative skills at a time when you could actually put them to use. I told you to change your focus, didn’t I? I told you to do the things you wanted to do, didn’t I? Yeah. I did. You should have listened. Do you know how long it will take you to get back just a fraction of those skills? Don’t answer that, because the truth is that you never really will. But at least you know now that there are other things you should focus on besides the narrow set of activities you’ve defined for yourself as your “specialties.” Pivoting is more than just Silicon Valley-speak. You can pivot, too.

To me, age 33: Great, you’ve got the job! Now start looking for a new job immediately, because you’re going to be gone in a year or so when that one company buys your company and then the other company buys that one company. And this town has never been good to you when it comes to career stuff, so maybe check out some of the other towns you’ve been interested in when you’re on the hunt.

To me, age 34: The thing you are going to do with your severance package? That is a great idea. I mean, I actually can’t believe that you thought of it. It’s not really out of character for you, necessarily, I just didn’t see it coming in your mid-30s. Some might say it’s a bit drastic, but hey — drastic times call for drastic measures. Good job. Do more of this. Enjoy the beach, too.

To me, age 35: OK, don’t get me wrong, I am a little concerned about the cashflows, but you can make this work. Focus on the job, because you won’t be doing this forever, and it will be motivationally revitalizing. Enjoy the company, too, because you’ll leave one day, and you might not make it back except for the occasional vacation. These are those “better friends” I kept talking about.

To me, age 36: Why did you do this? You hate this industry. For a paycheck? It’s not even a good paycheck! You know what? You’ve learned enough here. The last couple of years have been transformative. Let’s refocus for real this time now that the motivational reserves have been refreshed. Dig deeper. No, not deep enough. No, keep going. Deeper. There you go — now keep digging.

To me, today, and to me, in the future: Remember what I told you.

This story is republished from my original Medium article.