PicoBlog

The first gray hairs started showing up before I was old enough to buy a beer. Heck, I wasn’t even old enough to vote and suddenly old-person things were happening on my head. I wasn't ready. For a while I shaved it. All the way, meaning bald. My hair wasn’t thinning—that would come later—but in removing everything, I didn’t have to face the gray.

At the same time I was something of a prodigy. I started as a sub rep with Quiksilver when I was 18. In four years of sales meetings, when all of the reps would gather alongside staff in California, I was the youngest person in the building. The same was true when I went to Hurley for a bigger job—Florida Sales Rep—at 22. My peers were in there 30s and 40s but the leadership at Hurley saw something in me. They interviewed no one else for a job that paid six figures.

As the story goes, I would leave Hurley four years later to start To Write Love on Her Arms, not because of some dream or plan to create a non-profit, but because of the incredible response to an attempt to help my friend Renee Yohe. The story I had written and t-shirts I was selling to raise money for her treatment—the combination had become a phenomenon, translating to an opportunity to do more than help one person. Leaving Hurley was not an easy decision—it meant quitting my dream job—but what was happening with TWLOHA felt like a chance to bring my heart to work, to see people get help and stay alive. This was too special to walk away from.

And then it all made sense. All the dots connected. My mom once said that TWLOHA was everything I had ever learned and loved and shown interest in—from wanting to help people to writing to t-shirt designs to music—all under one roof. In junior high and high school I would daydream and doodle, imagining different brands. Now the dream was real and it was more than just a company. There was so much meaning and purpose. I had a lot to learn but it was exciting and people were paying attention. Amazing doors were opening. I was right where I belonged.

***

For the first nine or so years of TWLOHA, I didn’t shave my head. We’re talking about the peak of emo hair and I was friends with half the bands on Warped Tour. The thinning on the top of my head wasn’t going to keep me from taking a flat iron to the front. It’s true that dark brown is my natural hair color. Or it was when I was a kid. If you see a photo of me taken between 2006 and 2015, my hair is dyed dark brown. I was super insecure about this. A bald spot AND gray hair before 30? I could handle one or the other but not both. I wasn’t ready to be honest about it. And so a monthly trip to the salon, for the haircut but mostly for the color.

At the end of 2015, a friend introduced me to a woman and I fell in love. It happened fast and I could not have been more thrilled. We lived on opposite coasts and one day, in between visits, I FaceTimed her during a haircut. This wasn’t the usual cut-and-color done by a professional. This was me standing in my bathroom, taking matters into my own hands. The clippers were out and everything must go.

I didn’t want to color my hair anymore. I didn’t want to hide. I felt secure in our love and I reached out to share the vulnerable moment. I wanted her to see me. FaceTime removed the distance between Florida and British Columbia, and I removed the artificial brown. The little bit of silver of course scared me but I liked that it was honest.

Our relationship would end a couple months later, and I would be devastated—I wrote about this in the expanded edition of If You Feel Too Much—but my hair has been buzzed ever since. A case can certainly be made that the shortest possible haircut is just a different form of hiding, but there has been no other color since that day. The gray hair bothered me for a long time. I don’t notice it now. When I look in the mirror, I just see myself.

We announced my exit from TWLOHA on July 7, 2021. Two years ago today. And so I’ve quit my dream job twice. Only this time I didn’t leave to start a global movement. The transition was something humble. I basically walked away to bet on myself. I wanted the freedom of a blank canvas, a new chapter. Fast forward two years and I’m still figuring out what Career 3.0 looks like. Will this work? Will the pieces fit and will they add up to something sustainable? Will I still get booked to speak? Will people pay to support my writing on Substack? Will I write another book? Will I start a podcast? Will I ever get out of debt? Will I ever buy a house? The jury is still out across the board, and the clock ticks different after 40.

Those are just the practical questions. The deeper ones go beyond paying bills. If I’m not connected to TWLOHA, will people still be interested? If I’m not connected to TWLOHA, am I still interesting? The relationships I thought would get easier when I left TWLOHA, how do I hold the disappointment that they haven’t? Do we just keep ignoring the elephants in the room under the guise of boundaries? That thing they said to me that I cherished, that thing they just forgot about, am I supposed to forget it too? Do I fight for my connection to the organization or do I let it go? And what the fuck is a legacy? Do I care about that?

Coincidentally, today marks three months since the launch of Ever Get Home. After years of not writing, I began to write again. I’ve been doing it consistently since April. My hope was and is to see if I could fall in love with the process again, and to generate some income. If I’m honest, the hope is also to let the momentum lead to finally making a second book happen.

If you’re here as a free subscriber, thanks for being here. Thanks for being curious and thanks for reading all of this. If you’re here as a paid subscriber or a founding member, I can’t thank you enough. Thanks for allowing me to treat writing like a job. Thanks for believing that my work has value, not just in theory, but to the point you’re willing to pay for it. That means a ton and helps a lot.

I suppose the reason I’m sharing all of this is to say that if you’re walking through a difficult transition, you’re not alone. The thinning hair. The going gray. The changes in your health. The divorce. The affair. The grief. The job you loved but lost. The chance you had but feel you fumbled. The chance you never got. The how-did-I-end-up-in-this-place. Welcome to the fallout.

I don’t have the perfect speech or magic formula but I want to say I’m glad you’re here. Here on this page and more importantly here alive and breathing on this planet. You still have value. You still have talent. You’re still enough and still worth knowing. And life can still be good. Life is still worth living. I hope you get to participate in work that feels meaningful and I hope the work allows you to pay your bills. I also hope that for myself.

(Small spoiler for season two of The Bear ahead)

In the first season of The Bear, Cousin Richie is a rough character. He’s intense. He can be angry. And yet there are moments of sweetness and humor and loyalty and I liked him. I didn’t love him but I liked him. In season two we learn more about Richie. We see some of what he’s lost and we come to understand that he feels lost overall. We see his pain and watch him grow. There’s a moment where after a few days away for training, Cousin Richie returns to work—a restaurant that’s getting closer to opening. We’ve only ever seen him in t-shirts and jeans, sometimes a hoodie. He shows up in a suit and everyone is asking about it.

In one of my favorite scenes, Cousin Richie apologizes to one of his coworkers. Natalie aka Sugar is also a longtime friend, closer to family.

CR: “I think for a long time, I didn’t really know where I fit. And I would shove myself into places and things where I definitely did not fit. And I think that that probably, definitely, made things worse. And I’m sorry if I took anything out on you and if I treated you like shit. Because I actually do think that we could fit good together. I could be good at things that you don’t really want to do. And you’re obviously really great at a whole bunch of stuff that I don’t know how to do.”

N: “That’s why you’re wearing the suit?”

CR: “I’m wearing a suit because it makes me feel better about myself.”

***

I hope you get to do the job. I hope you get to buy the house. I hope you have the conversation. I hope you start the thing. I hope you quit if that’s what feels right. I hope you find connection. I hope you fall in love. I hope you can forgive or be forgiven, even if the person is yourself. Wear the suit or your version of the suit. Keep coloring your hair or rock the gray. Grow it long or shave it off.

Maybe leaving was my biggest mistake but I still want to see this through. By this I don’t mean what comes up when you google me. The word founder doesn’t tell you all I’ve found and all I’ve lost. The people who judge me most are not the ones who know best. My counselor knows more than anyone and I get the feeling she still likes me. Not just likes me but believes in me. Someone can only judge a play up to the moment they decide to leave the theater. They have every right to skip the ending but they can’t possibly know the scenes they miss. And so by this I mean my life. I want to keep learning. I want to keep growing and changing. I want to stay open and remain soft and sometimes I want to be strong. I can be intense and that can be the worst thing about me and it can also be the best. A recent ADHD diagnosis has been a game-changer. Medication has been a huge help. I remain forever grateful for counseling.

TWLOHA was born from all the parts of me, including my intensity. Last fall I stood on a small stage in Nashville, at an event where every speaker was invited to tell a story about failure. I shared some of what I’m sharing here. I touched on TWLOHA’s campaign for World Suicide Prevention Day, which was based on the statement, “You are not a burden.” With tears streaming down my face, I said “I don’t think the organization can say those words to me.” I went on to read There Is Still Some Time from my book. It’s where the title comes from but I changed feel to fail throughout.

If you fail too much, there’s still a place for you here.
If you fail too much, don’t go.
There is still some time.

My favorite characters are complicated. I am also complicated. I was at my best that day.

Give a gift subscription

Join me one week from today (7/14) for “I Want to Start Something New,” a small-group conversation for those in need of a new chapter.

If you’re curious about working together one-on-one, booking a speaking event, or checking out the merch, JamieTworkowski.com is the place.

ncG1vNJzZmiikaK2psDWqKmkp6eouKp60q6ZrKyRmLhvr86mZqlnna56tcPLqJ%2BaZZWttrV51pqqZpmeo7y2usKem2asp6Q%3D