When you record an entire season of a podcast 4 months before you release it, there are bound to be some changes in the world. Maybe a hockey team in Missouri wins the Stanley Cup. Or the Super Bowl. Maybe Justin Bieber releases a new album or Julia Roberts gets divorced. We were prepared for all of this. What we weren't prepared for was 2020.

COVID slowed things down but we pressed on anyway. But the death of George Floyd and the subsequent outpouring of grief, anger, frustration, and pain has felt different. Like it's not something we should just "get through" so we can "get on with it." Like maybe we should actually sit in this moment for a bit longer. And take a step back from the other conversations we've been having - important though they may be - to actually learn from and listen to the people for whom race and discrimination aren't just political talking points that they can engage with or ignore as fits their mood.

America is having a painful, uncomfortable, and long-overdue conversation right now about who we are as a country and about the work that remains to be done to create a future that includes all Americans. And now doesn't feel like the right time to change the subject and get #BackToWork.

So we're taking a break this week. We love talking to people who have their dream jobs and we're excited to host more of those conversation in the weeks ahead. But for this week, we want to spend more time listening, learning, participating, and processing. We hope you're well. And we hope you're doing the same. Back next week.

• Maintaining Professionalism In The Age of Black Death Is….A Lot
• 16 Tips For White People

It's June, and schools across the country have dismissed kids from their Zoom-fueled trances for a summer of bothering parents trying to work from home. Given the prominent (and unexpected) role tech played in school this year for millions of kids, what better time for The Dream Job Podcast to focus on education, and the promises (and perils) of EdTech?

After tackling how tech failed Kent and Onnie's youth, Kent's rough-and-tumble education in Oklahoma, and whether Oregon Trail was actually a good game (or just better than the other available activities at school), Kent and Onnie are joined by the one-and-only Tom Pryor, Head of Product at Class Dojo, an EdTech startup that connects teachers with students and parents to build amazing classroom communities. This conversation was recorded prior to COVID, before companies like Tom's grew 100s of percent to help schools adapt to a new normal of remote learning. Join us as we talk about Tom's affinity for clever Halloween costumes, his role as Head of Product and what that actually means, how to think about balancing impact and scale, how to maintain optimism even in challenging sectors like education, and the importance of balancing community, especially when you have your dream job. #backtowork

Links:

• Tom's Instagram
• Class Dojo
• Mavis Beacon
• Khan Academy
• Harvard's Grant Study
• Millennials are lonely
• Play Oregon Trail

It’s a special Memorial Day edition of the Dream Job Podcast! “Special” because it’s being released on Memorial Day. And for literally no other reason.

After a meandering conversation about Amazon (all hail), Chuck E Cheese, the NSA watch list, and TikTok, Kent and Onnie are joined by Pete Loizzo, Area Scout for the Cleveland Indians. This conversation was recorded back when baseball was still a thing and back when Pete was still traveling 200+ days a year to scout high school and college players throughout the mid-Atlantic states. (And single-handedly keeping Holiday Inn Express in business.) We talk about the highs and lows of life as a scout, the importance of working for an organization you trust, and the conflicted experience of watching Game 7 of the 2016 World Series as an Indians employee who’s rooted for the Cubs his entire life. It’s a fascinating look behind the scenes at the “business of baseball.” And it may be just the dose of sports you need to get you through another week where Survivor is the most compelling competition on TV. #BackToWork

• Pete on Twitter
• Trouble With The Curve (Wikipedia)
• Cleveland Indians

Things we never thought we'd talk about on a podcast about dream jobs: transgenderism in the military, foreign money in American elections, and the mass deportation of Liberian immigrants. We hit all three (and learn about the creepy nightclub where Onnie met his wife!) on this week's episode. And we still have time for a deep dive into the ins and outs of political fundraising and petty bickering about who the "real" host of this podcast is. All in a day's work. 

Our guest this week is Tyler Deaton, a political lobbyist and fundraiser who focuses primarily on causes related to human rights and free markets. We try really hard to "talk politics" without getting anyone dis-invited from Thanksgiving dinner. We're aided in that effort by the fact that we recorded this conversation pre-COVID, back when we thought people would actually care about the 2020 presidential election. At this point, any conversation about politics that doesn't immediately devolve into shouted accusations of who's trying to bankrupt who's family business and who's trying to murder who's grandma feels charmingly quaint. So come for the reasonable, non-pandemic politics, stay for the #ProTips on bribing Capital Hill guards. #BackToWork

• Tyler's company
• Tyler's Instagram
• Tyler's Twitter

If posted as a job description on your company's careers page, the life of a Mom would attract fewer applicants than that entry level sales role that's been unfilled since the beginning of time. In fact, it would probably be flagged by OSHA as an unsafe and abusive work environment. The work is exhausting, unsanitary, and (often) embarrassing. There's no pay, no opportunity for promotion, and no objective definition of success. Job training? None. Work hours? All of them. Unreasonable coworkers prone to frequent emotional meltdowns and verbal abuse? You betcha. 

Thankfully, despite all of this, millions of brave women still sign up for the job every year. The future of the human race (very literally) depends on them. And thankfully for us, one of those women agreed to talk with us last week about her life as a mom. Amy Evon, full-time mom and full-time sister-in-law to Kent, joins us for a special Mother's Day edition of the podcast to share about the highs, lows, and hilarity of her life as the mom of Susie (9), Emma (7), and Quinn (4). If you've ever wondered how you would handle a child pooping and puking at the same time, this episode is for you. And, if you forgot to say something nice to your Mom yesterday, consider yourself reminded. #backtowork

For this week's episode, we decided to social distance from our guests and talk to some numbers instead.

As much as we've loved talking to real people working jobs they really love, and as excited as we are about having even more of those conversations, we wanted to take a step back to frame the "thesis" for this podcast in light of the available data. This podcast started with a simple idea: meaningful work is a necessary component of a meaningful life. But is that really true? Is it just something Millennials say to justify their pathological inability to stay in a job for longer than 24 months? Are there other macro trends at play that make it challenging (but no less essential) to structure our work in a way that provides purpose beyond a paycheck?

This episode attempts to answer those questions while also unpacking the uniquely-Millennial hangups and neuroses that make meaningful work especially challenging in 2020. Like most of these early episodes, this conversation was recorded months ago and, therefore, has no knowledge of the impending COVID calamity. (Ah, December...such a simpler time.) But it doesn't make the data any less relevant or any less true. Give it a listen! And let us know what you think.

Articles and data points referenced in the episode: 

• Workism is Making Americans Miserable (The Atlantic)
• How Millennials Became The Burnout Generation (Buzzfeed)
• Life purpose is significantly correlated with all-cause mortality
• Embracing community leads to longer, happier lives (HBR)
• Millennials value paychecks over purpose (Gallup)
• The Enormous Cost of Unhappy Employees (Inc.)
• Millennials and loneliness (Vox)
• Millennials are poorer than previous generations (Financial Times)
• 95% of teens say having a job they love is extremely or very important to them (Pew)
• Why are young people pretending to love work? (NY Times)

There’s nothing business leaders love more than a good mountain metaphor. They’ll tell you that the life of any company involves “peaks and valleys.” They’ll tell you the rest of the year is going to be a real “uphill climb.” They’ll find a way to work “summit” into the name of their annual conference. 

But today, rather than hearing some stuffy exec tell us about the “mountaintop experience” he had at a Tony Robbins seminar last fall, we thought we’d talk to someone who actually climbs mountains for a living. Jess Matthews, Lead Guide for RMI Expeditions and the veteran of 100s of summits in Washington, Alaska, and around the world, joins The Dream Job to talk about how she’s 10x more badass than you in every possible way. Our words, not hers. (But if you're really being honest with herself...probably your words too.) 

She talks about working up the courage to leave her “old life” and pursue a crazy career in climbing. She talks about the centrality of things like sacrifice and service in her work. And she shares tips on what to do when you find yourself on a mountain with microwave-sized chunks of ice flying down the hill in your direction. Hope you enjoy this conversation as much as we did!

• Jess on Instagram
• RMI Expeditions

What do DJ Khaled, Manny Pacquiao, and Carmelo Anthony have in common? More money than you? Yes, that's correct. But not what we had in mind. What we had in mind was: they all have custom suits designed by Mr. Ton Chookhare. He’s a recovering management consultant, a business school buddy of Onnie’s, and - contrary to all evidence or reason - a  lifelong New York Knicks fan. 

More relevant to our purposes today, Ton is also the founder and CEO of Chookhare & Sons, a custom menswear company with showrooms across the country. It’s a safe bet he’d rather burn our combined wardrobes than be caught wearing any of it in public, but that didn’t stop him from sitting down with us to talk about starting his business, finding his passion, and fulfilling his grandfather's legacy. He also doles out some solid advice on what to do if/when you find yourself backstage with DJ Khaled and he starts asking you about your startup. Enjoy!

• Chookhare & Sons on the web | on Instagram | on Facebook
• Ton on Instagram | on LinkedIn

When you have the gall to launch a podcast about “meaningful work” in the middle of a global catastrophe that will radically alter our lives for years to come (if not irrevocably), well...it feels like you should at least take a minute to acknowledge that, yes, you’ve seen the news. So that’s what we’re doing today.

We started working on this podcast in November 2019. In the months since then, we recorded interviews with more than a dozen people. All of this happened BEFORE the world stopped turning and we all got sent home with a doctor’s note. When we started talking to folks about their jobs and their dreams, the unemployment rate was at an all time low (around 3%). It is now at an all time high with +20 MILLION people filing for unemployment in the last month alone. When we started this podcast, we were riding the longest and most lucrative bull economy the nation had ever seen. We now appear to be headed toward one of the deepest recessions we’ve ever imagined. 

These realities have forced us to ask ourselves some questions. Namely: is this podcast even relevant anymore? Isn’t any job better than “no job?” And - if so - what does this podcast have to say to the millions upon millions of Americans who have lost their livelihoods (not to mention dozens of thousands who have lost their lives) in the past six weeks? Is now even the right time to be having this conversation? 

Not sure we arrive at clear answers to all of those questions. But we try our best. Back next week with our next interview. But for now… #BackToWork

Have you ever had an entire room full of successful, upwardly mobile peers eating out of the palm of your hand as you described the blow-by-blow details of one of your recent job-related phone calls? Probably not. But our guest today has.

For our first ever interview, we sit down with Collin Roberts, an NFL Agent at REP 1 Sports to talk about his journey from lawyer to professional sports agent. We talk about his 40 yard dash time. We talk about what he’d be doing if he hadn’t landed his dream job (hint: it has something to do with cults), and we finally work up the nerve to ask the one question we’ve always wanted to ask him: can he get Jon Gruden to be a guest on our podcast? It’s a beautiful moment. 

We really enjoyed recording this one and we hope you enjoy it as well. Be sure to stick around till the end to hear the unplanned (and unwelcome) cameo from Onnie’s 4 year-old. 

• Collin on Twitter
• Collin on Instagram
• REP1 Management