Swoveralls Comfort Club · February 2025 · Volume 3, Issue 2

The 100 Year Plan: Write It Out

By Kyle Bergman, Founder of Swoveralls ·

Kyle Bergman and colleague Tamau wearing early Swoveralls at the Birchbox office in 2018

from the archives: 2018 at the Birchbox (RIP) office where I worked full time while starting Swoveralls. Me and my colleague Tamau rocking Swoveralls from the first ever production run (the text behind us is photoshopped and actually said Birchbox, ha.)

The short version

Founder Kyle Bergman shares how a simple habit that started at his first job, writing down what he had to do, grew into a 100 year life roadmap you can fill out yourself. The issue also spotlights collector and Senior Comfort Coach Gracie Perez, and recommends the books of Derek Sivers.

In this issue

  • The 100 year plan: how writing things down lowers stress and widens perspective
  • Customer Spotlight: Gracie Perez of California
  • Things we love: the books of Derek Sivers, plus what Kyle is looking forward to

It was extremely cold lately, and I'm not just talking about the usual suspects like Chicago, NYC, or Boston. Snow in Atlanta? Single digits in Dallas? I'm typing this from Maryland and we were just released from Mother Nature's arctic tundra grip. I almost double layered Swoveralls, which would've been a first. I'm curious has anyone ever done that?

It's milder this week, but I won't be fooled (as I am every February) in to thinking we have made it out. There will be (at least) one more cold blast in March that will crush our souls, but then...hopefully then...maybe then...we'll make it to Spring.

Shall we?

The 100 Year Plan

In my first job out of college I was the assistant luggage buyer at Bloomingdale's.

Every Monday morning, I was responsible for compiling a recap of the prior week's sales performance for all luggage brands (about 12) across all store locations (about 27).

It was a time-consuming and tedious exercise involving excel, some archaic reporting tools, and a printer that never seemed to work.

Needless to say, my Sunday scaries were at an all time high, and there was even one weekend where I shed a couple tears thinking about my dreaded Monday morning tasks (checkout the below screenshot from a real Tumi luggage report from 2013 and you'll see what I mean).

A 2013 Tumi luggage sales report that Kyle Bergman had to compile each Monday

the bane of my existence (once upon a time).

I'm not exactly sure who gave me the suggestion, and it's possible I just started doing it out of sheer desperation, but one Sunday afternoon I wrote down a list of all the things I needed to do on Monday.

I immediately felt better.

I didn't actually "do" the things yet - that would've involved time travel into the future since I couldn't create the reports until the stores closed on Sunday, but even just writing down what I had to do alleviated so much anxiety.

So then I wrote down what I had to do for the week.

The feeling was almost euphoric.

Getting everything out of my own head and onto paper did something profound to my stress levels in the best way possible.

Nowadays, when I get overwhelmed...I write down a to-do list. It might contain business things, it could be personal things - it doesn't matter. My notes app on my computer and phone are filled with dozens, maybe hundreds of to-do lists. Digital post-it notes if you will.

For me, there's something about writing down and checking off a fresh to-do list versus adding to a new one that just works, but some people might like adding to the same list.

You might feel that so far I've just been stating the obvious - writing things down can make you feel better.

But then I took it a step further.

I started creating lists of things I wanted to do over the next month, or 90 days.

Then with a wildly crazy suggestion from my friend Michael, I took it to a whole other level, and created my 100 year life roadmap. And I invite you to do the same here.

Do I have the next 100 years mapped out? No, not really. But even just filing out your age in the template (which I shared with you above) is such a powerful perspective exercise I felt compelled to share it with you.

How old will you be in 2045? How old will your partner or kids be? What do you want to accomplish in the 10 years leading up to that milestone?

These are questions we don't ask ourselves ever day, partially because I think their hard to answer. But similar to the money luggage report antidote I found, I think this exercise can change people. In a good way.

So I leave you with the 100 year template I made for you, and would love to hear your thoughts on going through the exercise (you can reply here, I respond to every email).

Customer Spotlight: Gracie Perez

Swoveralls Comfort Club member Gracie Perez in emerald velour Swoveralls and matching crocs

Gracie rockin the emerald velour swoveralls...and matching crocs.

This month we're highlighting the one and only Gracie Perez, a Swoveralls Senior Comfort Coach, Comfort Club Member, and just a lovely person.

Gracie lives in California, and first joined the Swoveralls family back in July 2023 when she picked up a pair of the limited edition Denim Heather style we made. Since then, Gracie has collected dang near close to every style we've launched.

To me, Gracie embodies our purpose of making people more comfortable with themselves. Whether getting on a plane for the first time, getting a root canal, or dealing with sickness, Gracie is in her Swoveralls, not because she has to be, but because they bring her a little extra comfort when she needs it.

Thank you Gracie for being a part of this comfy fam, and bringing Swoveralls on all of your adventures.

In Other Comfy News

Things We Love: Derek Sivers

A dear friend of mine (actually the same Michael I mentioned above) gifted me a couple books by Derek Sivers, who I had heard of only in passing, but had never read.

I don't believe it's a stretch to suggest that Derek is a modern day philosopher. His books will make you think, and maybe similar to this newsletter, state some things you believe to be obvious, but done in a much cleaner, thought-provoking, and articulate way than I ever could.

So far, I've read Anything You Want, Useful Not True, and Hell Yeah Or No, and have enjoyed all of them. These books are different from a novel you might read once, and I think are closer to guides I know I'll find myself coming back to.

If you check any of his books out please let me know what you think.

One Last Thought

On theme, I'll end with a list of things I'm looking forward to over the next few months:

  • Our baby girl joining us in June
  • Spring in Maryland
  • A half-marathon I'm running with some friends
  • Restocking core Swoveralls and Swovie Shorts
  • Being able to actually wear Swovie Shorts outside again
  • Earlier sunrises (big morning guy)
  • The overall (pun intended) energy that seems to pulse from the animal and plant kingdom as we emerge from another Winter (and a tough one at that).

Yours in free waistband energy,

Kyle Bergman signature

Founder | Chief Swoveralls Officer

PS - Have any comfort recommendations you'd like to share? Feel free to reply here and let me know. I'd be happy to include in a future newsletter and of course give ya a shoutout.

PSS - Love this newsletter? Can't stand it? Reply here and let me know and I'll personally get back to you. Your feedback is a gift.

PSSS - If you made it this far, you might as well join our facebook group here (the Comfort Club).

Key takeaways

  • Writing down a to-do list, even before doing any of the tasks, was what lowered Kyle's Sunday anxiety at his first job as an assistant luggage buyer at Bloomingdale's.
  • The habit scaled into a 100 year life roadmap, a free Google Sheets template Kyle shares so you can map your age and goals across future decades as a perspective exercise.
  • Customer spotlight Gracie Perez, a California Comfort Club member, first bought the limited edition Denim Heather style in July 2023 and has since collected nearly every Swoveralls style.

Frequently asked

What is the 100 year plan exercise?

It is a life roadmap Kyle built after a suggestion from his friend Michael, shared as a free Google Sheets template. You fill in your age across future years and note what you want to accomplish, which Kyle describes as a powerful perspective exercise even if you do not map out every year.

Why does writing a to-do list reduce stress?

In Kyle's experience, getting everything out of your head and onto paper lowers anxiety on its own, before any task is done. He found that simply listing what he had to do on Monday, and then for the week, made his Sunday scaries far more manageable.

Featured in this issue