It’s 6:00 AM on a Monday, and millions of people stare at their bathroom mirrors, dreading what will happen in the next few hours. All over the world, people will clock in at a job they hate that makes them feel dissatisfied, which has taken over so much of their personal lives that they feel empty.

Of course, it hasn’t always been this way. When we were younger, we bought into several ideas that we learned in school, that our parents taught us, and that society held as truth. If you show up and work hard, your contributions will be rewarded. In the world of our parents and those before them, that world did exist. But that world doesn’t exist anymore for many people staring at that mirror at 6:00 AM on a Monday.

The pandemic has changed the meaning of work for everyone. That’s not surprising. What is surprising is the insistence by some companies — or, better to say, the upper management of some companies — that nothing has changed despite the evidence and would like to return to the business model that suits them best. If successful, it would be one of the only times the toothpaste has been returned to the tube successfully.

For one group, the pandemic has caused more than just a redefinition of work but also a reprioritization of work related to the rest of their lives and the kind of work they’d like to be doing. So after years of working at jobs with little to no advancement, recognition, or reward, they leave those jobs, deciding to keep their talents at home and use them to benefit themselves. They are writers, photographers, podcasters, audio editors, video editors, graphic artists, etc. They are creatives. They are in their 40s and 50s. They have set a new course for themselves after half a life of doing something that didn’t fulfill their need to Be.

They are Mid-Life Creatives, and I am just one of this great talent migration, and this movement isn’t going to go away. Here’s why.

No security

One of my grandfathers worked for General Motors for decades, the other for American Airlines. My wife’s grandfather worked for Ford. It was a different time back then when a company hired you, and you had job security. Workers had rights, and there were strong unions to protect those rights.

Today, job security is an illusion. The days of working 40 years for one company for a gold watch and a pension at the end is gone. Not only that, but the world of at-will employment now means that we can arrive to work one day, and they advise us that our services are no longer needed. Not for any performance or disciplinary issues but simply because the company needs to cut its budget.

So, why continue to believe that lie and that worker protections will ever be strengthened, and unions will be reinvigorated? That job security will ever be more than an illusion?

No retirement

The previous generations had the security of Social Security and Pensions to fall back on in their retirement years. Then, in 1978, Congress established 401k plans. But unfortunately, while 401k plans offer workers the ability to save for their retirement, we have often seen how less stable they are compared to pensions over the past twenty years. That’s because 401ks are tied directly to market performance, and defined benefit plans like pensions aren’t.

The market would like to tell you that overall the performance of the market is bullish in the long term. Still, we’ve seen stories of people on the verge of retirement having their savings wiped out, as well as stories of the fees on withdrawing money — even after retirement — taking up to and over half of a retiree’s savings. The very design of 401k’s lets the gamblers play with the house money and keep as much of it as possible.

In addition, the previous generation had Social Security to add to their income in their golden years. So we all pay into this system. Still, people of my age and younger can’t expect Social Security to be there when we retire as the previous generation continues to deplete it faster than the tax base pays to keep it solvent.

So, knowing this, why continue believing in the illusion of retirement when the system won’t be there for us?

No equality

The American Dream is just as much a melting pot of ideas as America is a melting pot of people. However, the overall concept is that everyone has an opportunity to succeed. You’re promised the same shot as the person next to you. However, that’s not true for a myriad of reasons.

We live, whether we choose to admit it or not, in a classist, sexist, and racist system. A ruling class has set up this system to benefit themselves by transferring wealth to their coffers and keeping it through monetary and social policy. That same ruling class tells us that we can have a seat at the table if we follow the rules, but the rules keep changing. They also tell us that the reason we don’t already have a seat at the table is that there’s a set of people trying to take that seat away from us. So instead of fighting the ruling class, we fight that set of people. In truth, they aren’t fighting us; they’re trying to follow those same rules. The ruling class sets us against each other, and when we fight, they win.

There will never be class, gender, or income equality in our system. Despite years of happy talk about the American Dream and have equal opportunity to sit at the table, the ruling class doesn’t want that to happen. So why continue to believe the lie, and hope that the people in power will do anything about it?

Now, that’s a lot of negativity thrown at the Powers That Be. It’s harsh, and some of you may not take the same view I do. But, we can agree that whatever you believe, the pandemic has changed much about how business works.

After 18 months of the world on pause, we’ve learned a few things. First, the pandemic made us realize that:

Businesses are not families

The corporate line that “We’re a family” is hogwash. It’s time we stop believing it. We’re cogs in a piece of massive machinery, and we’re replaceable. I’ve had to learn this lesson twice.

You can work over 40 hours a week for a company habitually, have excellent performance reviews, participate in corporate activities, volunteer for corporate initiatives, be appreciated by your colleagues, and still be on the chopping block if the company decides you’re no longer needed.

There is nothing ‘family’ about that.

The Status Quo is gone

Had they made an effort to keep their human capital during the pandemic, the status quo would have been maintained. But, now that things are angling back towards normal, they would like you to forget that for the past 18 months, we still did the job. It doesn’t work for them, you see. It doesn’t work for them because this ‘family’ doesn’t trust you any farther than they can throw their server room. No, they need you back here in the office so they can ensure you’re doing the job you’ve been doing all along. That’s what works for them.

But, what works for them doesn’t necessarily work for us. This long-term experiment in telework, which many businesses swore was not feasible, became a success. Millions of people learned they don’t have to spend hours in traffic, spend thousands on daycare and gasoline, or eat the gas station sub for lunch. Many of us no longer have to punch out to go to the bathroom, to be interrogated afterward about why we’ve spent so much time being ‘unproductive’.

We choose to live

We’ve finally realized that the final element of this Information Economy that we live in is the shedding of one of the Industrial Economy’s last elements: The need to centralize. You and I get it, but business hasn’t grasped it yet. Until they do, the Great Migration will continue, and many more people like me will find something else to do because we’ve realized that we can choose to live a life where our career doesn’t suck the life out of us. We can choose to do something for ourselves if the career path we’ve been on no longer brings us joy. We can choose to live and do something that calls to us and fulfills our need to Be.

Final Thoughts

Now is the time for the work-from-home employee. The independent worker. The freelance worker. It is part of the future promised to us but never realized. It is a future we need to fight for now because, with no protections, no retirement, and no equality, the risk is the same. If that is true, then we should act in our self-interest precisely the way a business operates in theirs.

It’s our time now. Let’s embrace it.

My wife and I celebrate our 27th Anniversary this year. Every year, it continues to blow my mind that two people so diametrically opposed finding ways to keep making this work. Years ago, a musician I’m very fond of coined a term for pulling off a seemingly impossible task. He looked at a large stage that would resume its primary duty as a city skyline the next day. He called the act of turning that expanse of buildings into a show the equivalent of “making a steamroller fly.”

I love that phrase.

You could argue that anything hard worth achieving is on the level of making a steamroller fly.

Still, it seems so appropriate in our case. If opposites attract, Mother Nature pulled off a miracle in our case. My wife is more thoughtful and calm, and I am a pinball made flesh. I love the ocean and will move back to the Caribbean tomorrow. My wife would love to live in a log cabin in the country with no neighbors. My wife loves Autumn. I think seasons are overrated and believe that if it’s too cold to waterski naked, it’s too cold.

There was an age before the internet, friends. Right now, you should be extremely thankful for that.

My wife and I are, in many ways, polar opposites. She cross-stitches, reads fantasy novels, and plays video games without apparent end. On the other hand, I podcast, love professional wrestling, and Cyberpunk stories. The last time I played a video game, it required a quarter.

Yet it works, and I’m glad it does.

The Week Of Fun

The Week of Fun is my cute little name for the days between the 20th and 24th of July. I generally take the week that encompasses it off. You see, the 20th is my wife’s birthday, the 21st is our Anniversary, and the 24th is my birthday.

At the time, the bank I worked for declined my request to take either birthday off due to availability. But, for some reason, they had no trouble with me taking the entire week off if I was getting married. So that’s what we did, and that’s how it started.

In 2014, I worked for a camera company, and the photography bug returned and hit me hard. I found a really great deal on a DSLR and two lenses at a pawn shop, and I was off. I was going out to different places and shooting, mainly by myself.

Up to this point in our marriage, the wife and I had never had a shared hobby. We’re very much the square peg in the round hole in many ways, and it had never occurred to me that she might like to come along.

So when she mentioned that she might want to do that, I was more than happy to oblige. I found a decent camera for her birthday, and we went shooting. That opened up a lot of doors. Soon we were driving up the Eastern Shore to Ocean City for the weekend and finding many things to shoot along the way.

Photography is part of every weekend, and it’s the best thing to ever happen to us.

Now, we find ourselves thinking of new places to go and things to shoot. Moreover, it turned out that photography was a gateway to finding ways to make our relationship stronger.

We Time

We’ve been married 27 years in July, and we’ve raised three neuro-divergent children, both of us with full-time jobs. So to say that there hasn’t been a lot of time where it’s just been Kim and I is a bit of an understatement.

Regarding photography time, it’s a scheduled time that’s just us. After raising three kids, each of us having a job, and of course, the past 15 months, in particular, it’s time for us just to go do something and be together.

On the shore, in the woods, or just long rides in the car to get where we’re going, it’s just us, and it’s an opportunity to reconnect with what it was that made this wonderful.

In situations like ours where there’s very little time or energy to do anything after kids are in bed, it’s easy to grab a book or a screen and check out.

Also, sometimes you just need to have ‘neutral corners’ if you’ve been having a disagreement. Indeed, we’ve done both those things, but what I have found is that the scheduled time on Saturday has given way to other things. Maybe one night, I’ll not bury myself in creative work. She’ll not find herself in a video game she can’t get out of, and we’ll sit in the living room and just watch more of a series we’ve found on the streaming service. Or we’ll go back and watch a movie I’ve never seen (of which there are plenty; I only just watched The Fellowship of The Ring for the first time). Or we’ll work out where the next adventure will be early in the week.

Communications Aid

Here’s one thing about me that some people find surprising: Negativity affects me profoundly. Conflict elicits an actual fight or flight response due to how I was raised, and flight is the option I choose most of the time. So I will hide from it if I can.

Now, my wife and I don’t argue much. That’s not to say we haven’t, because that’s silly. All couples have disagreements, and that’s why I embrace the concept of the neutral corner I wrote about earlier. That said, there have been times I have been hesitant to say something for fear it would start a disagreement. That’s a communication breakdown, and it’s one that was on me to fix. The problem was I didn’t know how to fix it. I didn’t have the tools.

Then, one day while we were shooting, I had a great shot of a heron and limited time to get it before it took off. My wife was in the shot, and I had a choice. Take the pic with her in it, ask her to move, or just forget about it.

This one sentence made everything else easier.

“Could you move, please? You’re in my shot.”

It doesn’t sound like much, but that was really hard for me to do. Thankfully, my wife knew this about me and understood. She graciously moved aside so I could get the picture. This was a massive breakthrough for me, and I told her this.

After that, it became much easier to talk to each other about other things and not listen to the kid in my head that was scared about bad reactions or hurt feelings.

Future Plans

Planning the weekend shoots has led to thinking of long-term projects we’d like to do. For example, I’d like to go and shoot Tangier Island, a small island in the middle of the Chesapeake Bay. It’s a unique place that is slowly sinking into the bay. I’d like to chronicle life on that island before it becomes impossible. A longer-term project is to do the same for small coastal towns along the East Coast, not unlike my hometown of Machias, Maine.

This is notable because we’ve lived paycheck to paycheck for most of the time we’ve been married. So we have resigned ourselves to the belief that future plans aren’t a luxury you can afford. However, it turns out that future plans aren’t a luxury; it’s a motivators. It’s a goal to set and then figure out the finances and logistics to make that happen. We agree that it’s complicated to travel much in our circumstances. Still, we’ve found a lot of fun and hope in the planning.

Finding a shared hobby like photography made what was already a good relationship with my wife even stronger. I’m so happy we found something to enjoy together and new reasons to enjoy each other’s company even at this point in our marriage. I’m looking forward to many more Saturday morning shoots and future adventures.

In the fifteen years that I’ve been a podcaster, I’ve used many different kinds of formats. Daily shows, weekly, long-form interviews, unscripted improv, monthly magazine-style. None of them have stuck with me as something I’d like to do long-term.

I’ve noticed the surge in seasonal podcasting due to the popularity of shows like Serial and the rise of True Crime podcasts. So I decided to experiment with seasonal podcasting and dedicate each season to ideas I’ve had swimming around in my head for thirty years. Once I committed to this idea, I found it remarkably liberating, so much so that I could come up with an idea and produce twelve episodes of a season in a matter of weeks. To my delight, this season has been the most popular in terms of downloads, unique listeners, and fan engagement that I’ve had in some time. It’s led me to believe this is where I should have been all along, and I will continue making seasons of my show from this point forward.

With that in mind, I’ve got some observations about why this switch to seasonal podcasting became a natural fit for me.

They’re easier to outline

The first decision I made was the number of episodes I wanted to produce in the season. At first, I thought ten was a suitable number, but after some thought, I upped it to twelve because I would let the next nine episodes drop weekly after an initial drop of three. With that decision, I gave a topic to each episode, wrote a draft, and then edited it down. Because I took the time to do this first, I wrote the scripts for all twelve episodes in about ten days. It was a much better process for me than the grind of prep, outlining, writing, and producing every three to four days.

There’s a beginning, a middle, and an end

A season of a podcast is the same as the season of a TV show. You’re telling a long story that arcs over weeks. In this season of my podcast, I spent the first three weeks establishing the character called ‘This Pirate.’ Then over the following weeks, I let him reveal more and more of himself until we get to the last episode, which is a callback to the first episode and a nice ending to the season. The first-person narrative of ‘This Pirate’ made the writing very easy for me. Still, as I move into the next season of my podcast and a third-person narrative, it will be vital to tell a complete story with a beginning, a middle, and an end.

You can explore a variety of ideas

The following season of my podcast will continue the This Pirate line, but I have other ideas for future seasons. One of these ideas has been in my head since 1989, the rest since 1999. Of course, they’re fictional and will require more resources than just talking into a mic. Nevertheless, this switch to seasonal podcasting has lit that fire underneath me to start writing these stories and put them out in the real world in a way I never could do before. Perhaps it’s better to say that I’ve never felt as empowered to put these stories out in the world before now. Regardless, I’ve never been as positive that I can produce these figments of my imagination as I do now.

I find them less taxing than a weekly podcast

A daily or weekly podcast is a Sisyphean effort of prep, outline, write, produce, distribute, and repeat. It’s almost too much for one person to do, and I respect anyone who can. I can’t. I’ve repeatedly tried, and with kids and a job and obligations, it’s just too much for this guy. While the effort it takes to create a whole podcast season in one shot may seem just as much a struggle, it’s just for a short time. Once done, I can move on to the next thing on my list, like Promotion, community building, and scheduling some downtime to prepare for the next season. The weekly grind creates anxiety for me, and when I have that anxiety, I can’t perform consistently. I would rather be anxiety-free and consistent than be bouncing off walls and podcasting on a hit-or-miss basis.

They can be pre-produced and pre-scheduled

After I wrote the 12-episode season, it took me another four days to produce and distribute them. So from the initial idea to distribution, I created 12 episodes in about two weeks. Pre-scheduling these episodes to drop means I have a podcast season that runs weekly until July 30th. I plan to add one more episode out of the Pirate character, but I plan to record that closer to the end of the season to include more behind-the-scenes material. So this podcast will end on August 6th, and by then, I hope to have most of the next season produced, tentatively scheduled to start around Labor Day. The mental bandwidth it gives me and the pressure it takes off me is priceless.

Consistency is built-in

You must maintain consistency in creativity to keep an audience engaged. After a while, if the audience can’t rely on you to deliver when you say you’re going to deliver, that audience will move on to someone who can. With this method, your consistency is built-in. You’ve guaranteed that there’s a new podcast dropping next week for the next couple of months while you’re working on the next thing. Because it’s a season, you can bake the expectation of a hiatus until the next season into the last episode of this season. As long as you tell your listeners what’s happening, they’ll be there waiting when you get back.

Promotion is easier

Let me get this out: Promotion has never been my strong suit. I know they won’t just come if you build it, but telling people that I’ve built, it has always made me feel — and this is a technical term — icky. I despise high-pressure salespeople, and I don’t particularly appreciate feeling like one. However, with the reclaimed time I have using the seasonal method, I can create graphics and stories for my social media accounts and pre-schedule those posts using Buffer. A bonus to this method is using my social media accounts to be me, which lets me feel better about the scheduled posts hawking my stuff. I tend to schedule those posts about four hours apart, so those posts are bookends on a sandwich, with me being a human in the middle.

The M Word

Finally, we get to the elephant in the room. Of course, the obvious upside to seasonal podcasting is the possibility of monetization. I uploaded all the podcasts in the season to Patreon. I offered early access to all the shows for five dollars a month, with the ability to access a subscriber-only podcast and a monthly get-together on Twitch. With this new way of doing things, I admit that the Patreon approach is not yet working. However, I believe it will take hold because the podcast is still growing. Looking at the data for my show, I reached the total downloads for May on June 14th. On that trajectory, I should double the number of downloads, and if that trajectory holds, I should be able to continue outperforming the previous month. On the subject of unique listeners, I continue to attract new listeners every day, and repeat listeners return for the next episodes. I think it’s only a matter of time before the subscriber model starts working.

Conclusion

Of course, your mileage may vary. For me, this switch to seasonal podcasting has been the best decision I’ve made for my creative work since I decided to start creating audio for the internet back in 1999. So if you have a day job, family, kids, obligations, or you want to start a podcast but don’t think the weekly grind is for you, I would strongly recommend seasonal podcasting. I see no better way for me; I hope it works for you.

When I first started podcasting in 2006, I didn’t possess the technology to do interviews, so I left that out of my show for a long time. One of the first interviews I did in 2008 was with a gentleman named George Tabb, a NY punk icon and early activist for those who suffered from 9/11-related sickness. While it was a bit stilted and awkward, it gave me a definite idea of the kinds of interviews I wanted to do in the future.

I think the essence of a good interview is that it isn’t an interview at all. It’s a conversation. That’s why Larry King and Howard Stern are so good at their job. They engaged in a conversation with their guests, and in doing so, they could draw more out of their guests than intended. Someone who has appeared on Stern has said they told him things they would never have spoken to anyone else. I think that’s a high compliment, and it’s certainly something I try to emulate. Last year, I did a limited series of interviews on my podcast related to how people became creatives and how they stayed creative during the pandemic. I’m biased, but I think it’s some of my best work because I think I managed to get into a personal zone with people and gain their trust during the process.

I am by no means an expert, but I do know what works for me. So I’d like to share with you five things I would do when interviewing guests.

Do your homework

If your guest has written or appeared in anything recently, you need to know about it. Read and consume anything relevant to your conversation, and maybe go beyond that. I like to ask relevant questions, but I also look for human moments in a person’s bio, social media, blog posts, and videos. If it’s funny, all the better.

Now, you may want to tell the guest you found this moment and ask if it’s ok to bring it up. Don’t go for embarrassing the guest. It’s crass, and that guest has friends who will hear about it and never appear on your show. In my experience, the human moments we all share can be a real icebreaker or pressure release during an interview. If you can get the guest to share that laugh with you, you’ve got a good conversation going.

Listen. Really.

It’s easy to get sidetracked doing other things while the guest is talking. Riding a volume level, responding to chat if this is a live stream, posting quotes on social media, and other things. I’m asking you to stop that. Your focus should be entirely on the guest and what they are saying. I have heard my share of podcasts where The host prepared the questions well in advance, and the guest said something nullified a question, only to have that question pop up later in the show. That’s an unforced error, and you’ll pay for it. The other problem with not focusing on the guest is that it becomes very awkward. Sure, you can fix long pauses between questions in Post, but the guest may have a bad feeling about it, and it will reflect in their attitude, and the quality of their performance as the interview goes on. If you realized the person you were talking to wasn’t paying attention, how long would you stick around and participate? Exactly.

Be prepared to go off the list

I want to be clear about this point. I am not saying that you shouldn’t have a list of questions or a game plan for this interview. I am saying that if you’re actively listening to the guest, they may say something that opens up a whole new line of questions you hadn’t thought about and might be worth exploring. Conversations are not linear; you can drop one thread, pull on another one for a minute, then come back to the first one. That is what makes for an organic, authentic experience for the guest and the listener. If the guest feels you are in this experience with them, chances are they’ll trust you more, and they’ll loosen up and give you the interview you want

Stay in tune with the guest

You should be getting a good read on your guest as the interview proceeds, and you should be getting an idea of places you should and shouldn’t go. If you inadvertently head down a path the guest doesn’t want to go, and they might clam up a bit, don’t push. In some cases, the guest might say something they didn’t realize would take them down that path and then give you some indication that they’d rather not. If you hit a boundary, respect it.

Know when to end it

Ideally, you’re looking for an interview to take up a substantial part of your regular podcast, but like any party, you should be looking for hints that the party is ending. The guest might start giving you shorter answers or other context clues when they start feeling like they’ve said everything they need to say. When I get to that point, I have two questions I ask to signal the guest I’m starting to wrap up. I’ll ask what they’re working on now (or next) and how people can connect with them on social media. Then I’ll thank them and wrap it up. Know when that time is coming, and don’t stretch it out. An interview that goes too long becomes awkward later, and the listeners will pick up on it.

Interviews don’t have to sound like interviews; they can be all call and response and no substance. To get to something real, don’t treat it like an interview. Treat it like you’re just talking to a new friend you want to get to know. The result is a better product for you, a better experience for the guest, and trust as an interviewer grows in your field.

I want to start this by suggesting each of us ask ourselves a question: Am I OK?

I know that might sound simple, and you might think that’s ridiculous, but I’m dead serious. I want you to ask yourself if you’re OK, and I want you to be honest with yourself about the answer.

The reason I’m talking about this is pretty straightforward, I have had to ask myself this same question, and my answer is “I’m not sure.” I’m not OK, but I’m not in dire straits or anything. I can only describe myself as being in some weird limbo state that allows some things to pass, and other things stick and drag me down a little bit for a little while. I don’t know if anyone can relate to this, but maybe you can. It wouldn’t be the first time I’ve lost my audience by talking gibberish, and it certainly won’t be the last.

Basically, I’ve spent most of my time in the company of my family or outdoors, far away from everyone else. The main human contact I’ve had is with people that share my last name. I have seen other people three times in the five months we’ve been in this state. The only time I can tell you I am in the company of other people for any length of time is on Sunday Mornings when we do the groceries. I have not done any delivery side jobs since the shutdown because I think it’s dangerous. I lost a job I absolutely loved at the end of May. I’ve been looking ever since. I’ve been doing freelance work, but it doesn’t replace my income. I wish it did.

Some of you will tell me that I’m acting like, as one friend has put it, a covidiot. There are a few people in my life that believe that this thing has been blown out of proportion, that it’s not as bad as the news has made it out to be, that it’s a big hoax, and that I’m a sheep. If that’s what you believe, you’re more than welcome to believe that. You do you. What I’m not going to do at any point is argue with people about this because that’s time out of my life that I’m never getting back, and what I have seen out of the arguments I’ve read or been a witness to is that the anti-maskers are all about demanding respect for their rights, but not willing to respect the rights of others. I’m not into recognizing your right to put me in a possibly bad situation, but I’m not going to change your mind, and you’re not changing mine, so let’s just leave it.

I realize that I will probably have to break my promise to myself that I will never take another Customer Service / Tech Support phone call, and I hate it because the second I take that job, I feel like I’ve given up. I have done many things, but giving up is not one of them. Still, coming to that conclusion has not done wonders for my disposition. It’s depressing, to be honest. I had a great job, and I want to keep doing it. I just have to figure out how, and I don’t have much of a plan as I have a bunch of ideas that barely string together to form a coherent thought.

As near as I can figure, what I need to do is post content every day and promote the heck out of it. I need to reach out to people and ask if they need something I can provide, like podcast editing or Voice work, for example. I think I’m going to create a storefront to sell my photos somewhere. I’m going to write like the dickens and get it submitted places. I would like to start making videos again, and that one seems to be the hardest button to button. I suffer from what I’ll call “Neistat Syndrome.” I just don’t think my life is that damn interesting compared to people like Casey Neistat or Peter McKinnon, and while I know I’m comparing myself to two of the tippety-top YouTubers, It’s still a thing I’m dealing with. I need to think about the format.

In the end, I think I have what Michelle Obama says is a ‘low key’ depression, maybe? I don’t feel bad, I just feel resigned to certain things and disappointed. I’m fifty years old, and that’s a factor. I indeed have more time than my parents had; there is a limited amount of time on the game clock. So I’ll do what I always do. Work, and try to pull off the seemingly impossible.