#1: View from the Scenic Route

First of all, thank you to everyone who subscribed to this column in the past week. It will always be a surreal joy to have people out there who wholeheartedly support my creative endeavors before I’ve even proven that they’re good. Also, thank you to those of you who have submitted questions, it immediately brought me back to my If I Were You days and I’m feeling both totally dialed in, and right at home.

Now, let’s get into it. A decent amount of questions touched on this universal idea of not being where we “should” be in life. I feel equipped to answer this type of thing because as a fellow human, I have been there many times.

Dear Jake,

Here is my question, how do you deal with the feeling of being behind in life? I personally am not where I’d like to be career wise, have not found a long-term partner, and have yet to pay off my debts from my early 20’s. I’m actively working on changing these things, but it’s still a discouraging feeling in the meanwhile. Does it ever go away? Any advice/perspective?

- Drifting Delores

Dear Drifting,

These are big things to take on individually, and they only get tougher if you expect them to solve each other. It’s tempting to think the right job will cure the debt, and the cash will bring a new confidence that will find you love. But life doesn’t always stack so neatly, even though my OCD wishes it would.

Let me reframe it for a second and say, congrats on your blank slate. Lots of people feel stuck in work and love, but you are untethered and open to any possibility. You may not have it all, but you do have self awareness, because you recognized it. And you do have strength, because you are working to change it. So yeah, you are already doing exactly what I would recommend. But if that was my full answer then this wouldn’t be a newsletter. So let me tell you a story.

19 years ago (Jesus Christ that amount of time just shook me) I was on the Metro North on my way to New York where I had an interview to become CollegeHumor’s editorial intern. I was 20 years old and I had failed out of one college, dropped out of another, and was working part time at an ice cream shop. My friends were starting their junior year at colleges across the country, and I was living in my parents’ basement. I didn’t feel like I was being left behind, I felt like I had been forgotten.

Nothing in front of me was promised, the only thing I could guarantee myself was that I would recognize luck if it came my way. As it turns out, sometimes the low point is the launch pad. I couldn’t have known it at the time- I was so clueless that I wore a pair of Reef sandals to my interview- but that solo train ride across the Connecticut shoreline was the trailhead of my journey. A journey that has indeed had ups and downs, but one that I now realize never had anyone ahead of me, just a winding path that was all my own.

So yes, the feeling you’re feeling does go away. Then it comes back. And then it goes away again. That’s life. But the good news is that the more you go through it, the more familiar it starts to feel, and the easier it is to move ahead. For now, just know there are sections of this puzzle that are missing. But some day, maybe 19 years from now, you will be staring at a more complete picture and thinking about how fun it was to find all the pieces.

Godspeed.

Dear Jake,

In two months it will have been one year since I graduated college. I'm 23 and starting to see people pass by me very quickly in the job department, whereas I feel that I've achieved very little. I thought I had a lot of potential in high school, but since then I've made a lot of mistakes in my very short career so far and I feel very unimpressive and like I've already messed things up.

1. How do you deal with regret, and -

2. What advice would you give to younger people like me just starting their adulthood?

- Regretful Red

Dear Regretful,

See, told you guys there was a theme. How do I deal with regret? Maybe too well. My brain lets me to move on quickly from mistakes. The downside of course is that I have a hard time learning any lessons, and I make the same mistakes all the time. That said, if you are not someone who forgets easily, here’s some practical advice.

1. Don’t dwell on the downfall. If you’re going to overthink things, then at least think about them from every angle. You missed out on an opportunity? Don’t think about how that was your last and only one, think about what made it enticing, think about how you can recognize the next one better.

2. Be nice to you. My sister has something she says when she hears me getting down on myself, “Hey, stop talking shit about my friend!” Quiet voices in your head can get pretty loud. When they do, just imagine what someone who loved you might say. Or, what you might say to someone you loved. If that inner voice starts getting rude, remember to stand up for yourself.

3. Celebrate progress like success. Updating your resume, researching a company you love, even checking in with a friend about what they like about their job is all progress. You don’t need to tie happiness only to absolute success, instead tie it to forward momentum and intention, no matter how incremental.

4. Compare but also contrast. We can’t help comparing ourselves to others, I do that too. There are lot of dads on Instagram doing reverse lunges with their babies in their arms and I don’t know why the algorithm is targeting me with that but it’s fucking working, I’m jealous. Anyway, if you do compare yourself to people you feel are doing better, then also remember to contrast yourself against them. What makes you unique? If you can’t think of anything, see number 2.

At the end of the day I am a true believer of looking for the silver lining. Sometimes it is genuinely hard to find, and that’s okay. When that happens you just have to look up into the storm clouds and be grateful that you can at least feel the rain. Ideally while screaming back at the thunder and blasting this song.

Thank you for reading everyone! We will be back next week. In the meantime, you can click the button below to recommend this newsletter. That would be sick.

Want a Jake Take on anything going on in your life? Just send an email to just.contact.jake@gmail.com