The Blunder Years

I’m part of an elite squad known as the Special Victims -- no, wait, actually it’s just a Twitter thread called Just Be Social, which you can find at the hashtag Just Be Social or sometimes hashtag JBS. My second episode of this podcast was with Mollie, another JBS member, and this one is with Brenda Hill, who is Kansas City-based by way of Chicago and some other places. She’s had a varied, interesting career, and we talk about that. She also has two Gen Z sons, and we talk about her perceptions of what Gen Z might want from work as they start entering the workforce. We also talk about some ridiculous work crap and how one of my old roommates in Houston used to scream every Sunday afternoon about a portal being down. It’s a pretty fun conversation. Hope you dig it.

A few months ago, I was doing a couple of short podcasts with a guy that used to co-own a gym I went to. I think only 1 or 2 of them ever got published, but we did a whole episode on that idea that you are the average of the five people you spend the most time with.

Well, now I have this podcast, and this episode I’m talking to Cesar Espino, who is a real estate investor, coach, author, and logistics guy out of the Los Angeles area. We talk a lot about the “five people you spend time with” theory as well, and also discuss legacy, mindset, mental toughness, and your 20s vs. your 30s. Hope you like it.

I remember right after graduating from college, I had one core friend backpacking throughout Asia and Europe for a while. We all have some version of this friend or this story; as I’ve gotten older, I’ve met probably 12-15 other people that did this. The flip side of the whole deal is that you all have friends who dive into work at 16, 18, 22, whatever … and start hustling and earning money. Those people maybe have less “fun” in their 20s, but theoretically the idea is they can have fun at different points with saved money and then later on. Unless you have a trust fund, the idea of just backpacking around Europe and Asia is probably not feasible.

I turned 39 a few weeks ago and broadly I’m OK with my experiences thus far, although I wish I had invested more in my career back in the day. Well, I worked at a place briefly in 2018 in the cybersecurity industry. I had to go to Kansas City for an orientation and I met Steven McFarland, who kinda has a similar “focused on career later than others may have” path. He’s a cool dude and now starting to make career moves, so I thought I’d have him on this podcast.

This is a shorter episode because we spent some time at the beginning catching up on the place we worked together, and a lot of that wouldn’t interest you, so I killed it. But the stuff about the trade-offs we make in early to mid adulthood is important for a lot of people, so I thought that was a good essence here. Let’s get to it.

Back in October of 2016, when admittedly the world seemed a bit of a simpler place, I wrote an article called “An organizational consultant can’t save you now.” Probably four years before that, as I was leaving New York City, I actually really wanted to be a consultant. Less than a half-decade later, I had soured completely on the idea. In that article I wrote, I quoted a guy named Dan Rust who has a book called Workplace Poker. In that book, he equates work to “chimp rape.” Not kidding.

Ironically, that was one of the posts where I first started interacting with Anil Saxena, who has been a digital and e-mail friend of mine for about three years now. I wanted to bring him on this episode and talk about both life and work. Admittedly we probably spend 90 percent of the time talking about work, but work takes up a big chunk of the middle part of your life, so I was OK with it. We talk about psychological safety, the role of HR, the role of leaders, and at the end there’s a sequence about a crappy job interview he had and what it meant when he eventually took the role. Let’s get to it.

I lived in an apartment — the number was 234 — with my ex for about 34 months. Since I left my parents’ house back in probably 1999, I think that’s the longest single place I’ve ever lived. I moved out of that place, oddly 14 years to the day of my graduation from college, after we got divorced. The new place was Number 328 and for a chunk of time I lived there, I’d classify myself as “lost.” When I eventually donated the couch in 328 to the Salvation Army, there were cigarette burns on it. You get the broader idea.

Well, back in 234, I was writing virtually every day and starting to get some traffic and some traction as a freelancer. In that apartment, I appeared on one podcast taping … and the lady I taped with never ran it. A few months into 328, I appeared on this guy Paul Millerd’s podcast. He talks about work in different ways and has a cool approach to what “success” even is. His newsletter, which hits on Saturdays usually, is one of the best out there if you care about issues like work, learning, success, etc. So now that I’m doing a podcast, I wanted to have him on. That’s what this episode is. By the way, now I live in an Apartment numbered 603, but I’m still interested in these types of work and life and success and future issues, and I hope you are too. Godspeed, and let’s get to it.

If you’ve ever read my blog, you know I’m not always the biggest fan of management and leadership. There are great leaders in the world, for sure, but I’d argue the majority are disappointing -- and actually, years ago Gallup actually had a stat that 82 percent of managers end up being poor leaders and wrong for the role. 82 percent bad means 18 percent good. Imagine if you came home in junior high and scored a 18 on a test. You think your parents would be very happy with that?

So I was excited to talk with Devin Craig, who is a Seattle-based consultant focusing on a more human form of leadership. I know that can sound like a BS-y term, but this is a pretty interesting talk. I was expecting it to be about 25 minutes and it was almost double that because, I mean, who doesn’t like to chop up leadership and management? Maybe I am a nerd. Anyway, here goes.

This is probably the shortest episode I’ve done so far, but it has some really interesting nuggets in it. The guest is Dr. Gordon Pedersen. You’ll hear this story in the first couple of minutes, but around age 38, he went to Indonesia, got sick, came back to the US and went to the hospital, and someone in the OR dropped him on the floor, breaking his back and immobilizing him. Never fear, though -- by 43 he had won a Bronze Medal at the Utah Games. Believe he was the oldest medalist that year.

This is a good conversation about health and how health is all you really have at some level as you age. It’s kind of ironic because I taped this on a Friday a few weeks ago, and on the day before I think I had ended up having something like 9-10 beers across hanging out with different people. So, it was a nice level-set for me to focus on health as well. Plus: there’s some stuff at the very end about the difference between one minute of being angry and one minute of laughing on your immune system. Hope you enjoy the episode.

Aging parents is a concept that people are starting to talk about more and more. I’ve seen stats about 10,000 Baby Boomers retiring every day, but they’re retiring to lives that will last longer than they ever lasted before -- potentially we’re adding the equivalent of a third of life to people these days. Now that’s great in terms of time with loved ones at one level, but there’s a huge financial piece of the puzzle that we haven’t totally figured out yet. And this is all happening at a time when wages for most people have been stagnating for at least a decade.

That’s part of what I discuss with Brandy Henry in this episode. She’s an independent business owner in the Portland Oregon area and she hosts her own podcast about engaging on social media. Here we talk about aging parents, about the difference between 22 and 30 and 38 and 46, about how everyone is nuts, and about dichotomies around women at work and at home. Hope you enjoy it.

One of my good friends passed away two years ago; if you read my blog or newsletter, you may have seen some stuff about it. Actually, on the day I’m recording this intro, there’s a memorial Mass for him at Georgetown University, but unfortunately I lacked the funds currently to fly up for it. Well, when I did attend his funeral in October 2017, one of the things that stood out from that day is that this kid I had barely seen since college asks me in the pews, “So, do you think you will stay in Texas?” It was a logical question because I had been divorced a few months prior and maybe I would go somewhere else and reinvent. So this kid asks me “What’s your five-year plan?” basically as our friend’s casket is being pushed down the aisle. It was a pretty jarring contradiction and when I got back, I wrote a post about how dumb “the five year plan” feels.

That’s one of many themes in this episode with Brian Ondrako, who has his own site and podcast called “Just Get Started.” You should check his stuff out because he’s got some A-level guests on there. As you might guess, “Just Get Started” is about how there’s never a perfect time to pursue something -- so just for it. It’s a cool theme, and we talk about that, five and 10 year plans, North Stars, sleep, fitness, Instagram likes, and more. Let’s dive in.

I’ve written probably 2,400 blog posts on my main site since about October 2013. I did the average per day on that once, and it’s something like 1.7 per day. In short, I have blogged a lot. Once in a while people ask me what my favorite-ever post is, and I mean, it’s hard to choose because I barely remember everything I’ve written on here. But … I think in 2016, I wrote a post called “New product features? How about new people features.” The idea is that workplaces become obsessed with product launches and rollouts, and those are obviously really important to the business -- but every day, people go through stuff too. They get married, they get divorced. They raise kids, they (hopefully not) lose kids. Their parents age. Friendships change. They fight with their spouse. They reconcile with their spouse. All this stuff happens to us day in and day out and it changes our connection back to the work we do every day.

That’s a big theme of this discussion with Bob Brumm, who brands himself as an Encouragement Engineer. The origin story of that term is within the episode. He’s a professional speaker and coach focusing on a positivity mindset and helping people get through different challenges. I figured he’d be a good guest because the focus of this podcast is on the Second Act of Life, about 25 to 50, and a lot of different, very impactful stuff happens to people in that age range. Turns out my guess was right -- this is a relatively short episode of maybe 24-25 minutes, but we cover a lot of themes, including work-life balance, work-life integration, “the reality of life kicking in,” being human at work, whether “purpose” is a buzzword, and more. Let’s get to it.