Try It On

A big thank you to my sponsor who keep this newsletter free to the reader:

As the year is starting to wind-down, you’re might be thinking about setting yourself up for financial success in 2025. 3￠ Accounting , run by Tanveer Mall —if you noticed the name similarity, yep, that’s my dad!—is offering free consultations for readers of this newsletter to help set you up for financial success. I’m a client too: I had a 10-year financial independence plan that he helped me shorten down to only 2 years by redirect my income to a few different places and doing some restructuring of my savings. Whether it’s debt reduction, some forecasting, or other financial concerns, it’s at least worth a conversation. Visit 3￠ Accounting to drop them a line, and let them know I sent you for your free consultation.

Apropos for a Black Friday newsletter issue, I think you should know: I’m a shopper. I like shopping. It’s popular for designers to be minimalists and get by with as few material possessions as possible. I admire it, but that’s never been me.

I like possibilities. I like the multiverse, the potential futures that could be. When I try on a shirt or a pair of sneakers, I get to be a different person for a few minutes in that fitting room. And I get to decide if I want to be that person for longer than a few minutes. I don’t wear Hawaiian shirts because I don’t think they suit me, but I try them on every now and again to see if I’ve become the kind of person who could wear Hawaiian shirts. (Currently? No.) I like how Jordan 3’s look, but not on me. (I’m a Jordan 1 guy.) But I still try them on occasionally because I like thinking I could one day be the kind of person who looks good in Jordan 3’s.

This mindset extends further than clothing and physical appearance. I like thinking about who I am and who else I could be in a year, or a month, or a week, or tomorrow, or today. Am I the kind of person who starts businesses? I wasn’t, until I was. Am I the kind of person who can run a marathon? I’m not today, but maybe I could be in 6 months. I like trying on new versions of myself to see if they fit me. Our industry generally looks down on the idea of imposter syndrome, but I think it also has its advantages.

Lately, I’ve been trying on an uncomfortable idea. I’ve always been an ambitious person, constantly striving to reach new achievements. A new thought occurred to me: what if I actually have already achieved everything I’m going to achieve in my life? Though jarring, it’s plausible: my wife and kids give me a full and fulfilling life, I’ve experienced more business and career success than I had ever dreamed, and I’ve been able to impact the lives of many others through teaching, writing, speaking, and working. I know it’s important to not take exercise to morbid trains of thought like “I have nothing left to live for” or anything like that. I already know what it’s like to live like someone who wants more; what does it feel like to live like someone where everything new is a bonus, not a desire and certainly not a need? How would that person act, operate, and live? And how different is that person from who I am today?

Though uneasy, I’m trying it on.

I’ll report back on how it goes.

Who can you try on? And what doors does even the thought exercise open for you? Remember: like an ill-fitting jacket or a sweater can makes your skin look a weird color, you can always take it off if you decide it’s not you.

But can it be?

—Dan

P.S. - The Black Friday sale for my Design Systems 101 course is officially on! It’s regularly $101, but today it’s only $50. If design systems have been on your list to learn or learn more about, today’s your day!