Opening Note
June is when the plans stop being plans.
Summer is finally here, and the calendar has tipped toward all the things we spend the colder months only thinking about. The timing feels about right, because May was a month spent on exactly that: how to actually do the next thing instead of just circling it.
The thread through May was simple enough: spend less time talking about your next act and more time figuring out how to start one. Most of the month was practical, the nuts and bolts of getting going on something new. Then we ended it by turning all of that back on ourselves, each taking on five summer challenges with no way out. Turns out giving the advice is the easy part. Promising an audience you’ll lose twenty pounds or learn to ride a unicycle by fall is a different thing entirely.
A few things we have to say out loud this month. First, and most important, thank you. We’re now landing consistently in the top five percent of podcast downloads worldwide, and there is no version of that sentence that happens without you.
Second, the Message the Show feature has taken off, and we love it. If you’ve got feedback, an idea for an episode, or just want to say hello, it’s on every podcast player, by text or voicemail. Leave a message and we may share it on a future show.
One more from the tech side, and we’ll keep it short for everyone’s sake: if you listen on Apple Podcasts and you’ve updated your device to the most recent iOS, you can now watch the episodes, not just hear them. Nobody needs to stare at the two of us for an hour, but it’ll earn its keep on some of the episodes we’ve got planned, where there’s actually something worth seeing.
And one small change on our end: starting this month we’re moving to every other week instead of weekly. Nothing dramatic behind it. We’ve got plenty of the kind of adventures we keep telling you to go have, and keeping that balance means taking a little of our own advice.
We’re glad you’re here with us.
Podcast Recaps — May Releases
Episode 29: Before You Retire: 5 Things We Wish We’d Done First
Most people prepare for the money side of retirement and stop there. This conversation works through the other four areas that quietly reshape everything else: relationships, health, purpose, and adventure, along with the things Rob and Brent wish they’d test-driven before their last day on the job. It’s less a checklist than a look back at what we got wrong and would do differently.
Episode 30: A Guide to Earning Money as a Consultant in Midlife
A deeper follow-up to the earlier episode on earning income in your next chapter, this one gets specific about starting a consulting, advisory, or coaching practice. Between Brent’s twenty-plus years consulting and Rob’s newer advisory practice, they cover the foundational work most people skip and the six steps that get you to a first client. It all turns on one shift in how you see yourself: you are no longer the employee representing a company, you are the product you’re selling.
Episode 31: Launching a Creative Business in Midlife
If the consulting episode was the easy-button version of earning in midlife, this is the opposite: turning the creative thing you keep postponing into something that pays. Rob wants to shoot action video, Brent wants to restore old cars, and the conversation sorts creative work into physical goods, content, and services. They apply the same passion-product-marketplace framework from the previous episode, with a blunt warning that most creators underprice themselves and spread across too many platforms before they’re good at one.
Listen now
Links, resources, books mentioned: Mountain Mud Ceramics (creative business mentioned)
Episode 32: 5 Challenges We Got Ourselves Into
Instead of waiting for January when most people set goals, Rob and Brent each committed on the spot to five personal challenges for the next three months, one in every ring of midlife: finance, relationship, health, purpose, and adventure. Neither knew what the other would say, which is how you get public commitments to lose twenty pounds, track every meal for ninety days, join a Friday golf group of strangers, and learn to ride a unicycle. The results are due back on the show in the fall, with no take-backs.
Wisdom Drop
Advice is easy to give. It’s a lot harder to be the one on the hook for it.
Anyone can map out the steps for someone else. We hand it out confidently because the stakes aren’t ours to carry. The challenge starts when the plan has your own name on it. That’s the gap where most good intentions quietly die, the distance between knowing the right move and being the one who actually has to make it. Knowing what to do was never the hard part. Almost everyone knows what to do. The hard part is staying with it long after the motivation that made it sound easy has worn off. So, if there’s something you’ve been giving other people advice about lately, the real question is whether you’d take it yourself.
One Great Link
“The Old 96er…Seriously though, has anybody ever eaten one?”
In one of the great 80s comedies, The Great Outdoors, John Candy’s character sits down at a steakhouse with his family and accepts the deal: finish the 96-ounce steak, gristle included, and the meal is on the house. The chef brings out a slab the size of a coffee table. The whole restaurant watches. There is no graceful way out.
That is the trick, of course. Plenty of us can quietly walk back a goal we never told anyone about. Far fewer of us can walk away from a roomful of people who saw us order it. Most of the things worth doing in midlife stay theoretical until someone is watching, and the moment they are, the probability of quitting changes.
We’re not recommending you take on the actual ‘Old 96er’. But there’s probably something you’ve been circling for a while, and this is your cue to commit to it.
Closing Moment
There’s a version of June that everyone reading this remembers from their childhood.
The one where the day started with no agenda and ended with grass stains, and somewhere in the middle something interesting happened that you didn’t plan. That version is still available. It just takes putting the phone down for an afternoon and being willing to wander.
And when you do, we’ll be here, cheering you on from the front row.
See you under the tent,
Brent & Rob
Co-Hosts and Creators, Midlife Circus
midlifecircus.fm