Bradley Richardson: You're Not Reinventing, You're Remodeling
Bradley Richardson has been writing about Gen X since we were the young ones. He published one of the very first business books aimed at this generation back in the nineties, then five more on everything from being a dad to starting over. These days he runs Advanced Adulting, which he describes as helping grown adults navigate midlife and beyond. Not the nostalgia version. Not the shuffle dance and testosterone check version. The real stuff: your career, your parents, your kids, your money, and figuring out who you actually are now that nobody's telling you. He just turned 60, which he calls joining the freshman class of old people. A few things in here I haven't stopped thinking about. Reinvention is the wrong word. Everybody sells it like you have to become someone new. His version is remodeling. You strip the house to the studs, and the bones are good. What you're looking for isn't a new person, it's the person you were before the world and your job and everyone's expectations sanded you down. His take on ageism is not the take you've heard. It isn't going away, it's been happening since the dawn of time, and we did it too when we were the young ones complaining about the fifty year olds in our way. That doesn't mean you have no value. It means you have to create your own market now. He's done with the gurus, and he says he used to be one. His words: there are a lot of Gen X midlife bullshit artists out there and I've been one, so I can call it. Everybody's got a three step plan and a blueprint. He stopped doing that, because he's still figuring it out himself every day. He also has the best math on criticism I've heard. A third of people will decide they don't like you for no reason at all. A third are situational. A third are your people. That last third is the only one that gets a vote. We also get into the part nobody plans for: the two twenty-five year friendships he lost, not in a blowup but by slow drain, and his rule about it. You don't have to like what I do, you don't have to agree with it, you don't even have to understand it. But you do have to support it. Oh, and the video that got ten million views. "I'm fifty-eight and I'll never get hired again." In this episode: Thirty years of chronicling the same generation Why forward beats nostalgia Life in thirds, and what the next thirty actually looks like Ageism, and the uncomfortable part nobody says How Gen X got issued labels and Gen Z didn't Losing a company in 2000 and having to go get a job Choosing a school, a major, a job, a spouse on somebody else's expectations Remodeling instead of reinventing The friendships that don't survive, and the ones that do Worth is what somebody will pay today, not what you used to make Why he'd go blue collar if he were starting over The baseball rule, and why corporate makes you hit .900 Sixty by sixty, and what he's building next TIMESTAMPS 00:01 — Welcome 00:28 — Advanced Adulting, and what it isn't 00:50 — Thirty years of writing about Gen X, starting in the nineties 01:45 — Why he looks forward instead of back 02:17 — No pensions, uncertain 401ks, and thirty more years to fund 02:40 — Just turned sixty, and why he won't call it midlife 03:30 — Life in thirds 04:37 — Look back to learn, then stop looking 05:30 — Too young to be old, too old to be young 06:06 — "You don't know technology." We invented it. 06:47 — The ageism take: it isn't going away, and we did it too 07:25 — The pro athlete analogy, and the corporate equivalent 08:23 — Labels, and what Gen Z does better than we do 09:00 — The cocktail party question 09:23 — Losing the company in 2000, and having to go get a job 10:24 — Identity tied to title, industry, and employer 10:57 — Wall Street, Secret of My Success, and buying in 11:38 — Expectations, and choosing a life somebody else picked 13:23 — You get to choose you now 14:13 — Chasing energy 15:05 — Who's actually in your corner 15:24 — The two twenty-five year friendships he lost 16:19 — The four people whose opinion counts 17:36 — What's changed in thirty years of watching this generation 18:40 — Remodeling, not reinventing 20:08 — Stripping away the character corporate made you play 20:45 — Two years without an alarm clock 21:30 — "What kind of music do you like?" and not knowing the answer 22:30 — The Gen X midlife bullshit artists, and admitting he was one 23:07 — Life keeps handing you things you weren't prepared for 24:00 — Why he changed what he does 25:00 — The people who shout loudest 26:04 — The nine figure founder and the Walmart test 27:28 — Caregiving as the great equalizer 28:13 — The divorce cluster in Brett's last corporate job 28:54 — Married too young, and the no-quitter problem 30:14 — Divorced at forty-four, and bringing the same mistakes along 30:47 — "You're choosing the same damn thing" in careers too 32:36 — History doesn't mean you have a connection 32:51 — The "we're family" lie 33:05 — Work besties, and how fast that goes 35:00 — "I'm fifty-eight and I'll never get hired again," and ten million views 36:10 — The trolls, and why it isn't about being lazy 36:42 — Why he'd go blue collar if he were starting over 38:00 — What something is actually worth 39:24 — The Comfort Crisis, and the podcast that took Brett two months to start 40:31 — You're not going to be an expert, and you're going to screw it up 41:37 — The tennis points stat 42:14 — Why corporate makes you hit .900 43:09 — How he handles the comments now 44:00 — The thirds rule for people 45:32 — Where to find him 46:01 — Sixty by sixty, and the next thirty ABOUT THE GUEST Bradley Richardson is the creator of Advanced Adulting, a platform about navigating midlife and whatever comes after it. He's the author of six books, starting with one of the first business books written for Gen X in the 1990s, covering careers, fatherhood, and starting over. A former headhunter and a Division I tennis player at Oklahoma, he's been writing about this generation for roughly thirty years. He turned sixty in 2026. Instagram, TikTok and Facebook: @iambradleyrichardson YouTube: @AdvancedAdulting
