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1) To kick things off, could you tell us a little about your career background and current role?
I have two parts to my work. One part is running a media company I founded in early 2019 called Marketing Showrunners (MSR).
We cover the growing space of marketers who create original shows like podcasts and video series to build their brands, providing regular insights and stories to our audience.
MSR is the culmination of years of working for companies like Google, HubSpot, and a VC firm called NextView, where I helped build brands and advise other marketers or entrepreneurs about their content marketing.
The other part of my work is what I call “the quest.”
The quest starts with me getting angry at something that I think is broken in the marketing industry, then asking lots of questions and investigating them through story and science, then trying to distill into insights, themes, frameworks, and usable ideas. Said in a far less impressive-sounding way?
I wish something wasn’t so crappy, then I try to figure out how to convince the industry to change. In between, I have no idea what I’m doing so I try a lot of stuff.
The idea of “the quest” is something I learned from marketing author and speaker Andrew Davis, who helped me see the importance of focusing the creative process on investigation rather than pontification.
Think of it as the relentless pursuit of curiosity through research and creation, which I find leads to better breakthroughs than leaning back in a chair and trying to concoct “the idea.” The quest was previously something I just kinda did. But since that’s not very teachable, I tried to sketch it out below:
2) What does a typical day in the life look like for you? Can you take us through a recent workday?
The days vary because my projects vary. I’ll give you my day last Thursday, because it feels somewhat representative:
6:30am: My 10-month-old daughter woke me up, and although I felt like sleeping in, nothing is better than waking up to a tiny, adorable human with crazy hair, a big smile, and an urgent need to wave her little hand at a bunch of stuffed penguins on the shelf — like right now, Daddy, c’mon, get me outta this crib.
7:00am: While my wife, dog, and the baby slept (again), I wrote a quick blog post. I publish two or three short ideas about creativity in the workplace to my personal blog each week, which get automatically sent to my subscribers. Last Thursday, it was a post titled “Deconstructing the art of the interview.”
Fast forward to 9:30am: I’m alone in the house with the dog, just finishing breakfast, and it’s time to write an article for Marketing Showrunners. I have a recurring calendar invite from 9:30am to
11am every day that reads, “Write, even if it’s bad.” This is the most important reminder in the world to me: forward motion with the intent to be great, or putting down a bad draft to edit into something good later, is the most crucial step in creative work.
11:30am: I had my 1:1 video call with Tallie Gabriel, who is both a producer for Unthinkable (my personal podcast) and staff writer for MSR.
12:00pm: I created a list of target subjects for a 10-part video documentary series I was hired to host and direct for a brand client. We’re telling the stories of brands that seemingly shouldn’t exist due to giant, well-capitalized competitors, but they possess something that others can’t purchase: deep, genuine customer connection.
We’ve already shot and edited the pilot, and we’re finishing up episodes 2 and 3 now. We launch in 2020.
12:15-1:00: I forgot that lunch is a thing you’re supposed to eat and instead edited a clip of one of my recent speeches to post to social media. I periodically post stuff like this to help promote the speaking side of my business, which accounts for around 40%-50% of my annual income.
1:15-1:30pm: I panic-ate lunch, remembering that it’s a thing you’re supposed to eat.
1:30pm: I had my 1:1 video call with Molly Donovan, who is the managing editor of MSR. We plan out additional weeks of content to serve our audience of marketers, among other topics.
2:30-4pm: I edited a podcast episode for a forthcoming client show. While I’ve scaled down my client services business from 5-6 clients at once to 2-3 at once (in order to focus more on the media business model of MSR), I still have and plan to maintain one podcast client and one video documentary client per year.
For this edit, I tried to figure out how to take a 60-minute interview, plus music, plus sound design, plus some narration, and create a 45-minute final cut.
4-5pm: I appeared on a brand’s video show as a guest, calling in through Skype. (15 minutes of that was just dealing with Skype issues with the host. Online video and audio tools have one job: successfully connect two parties to talk. They also suck at one thing: successfully connecting two parties to talk.)
5-5:30pm: I checked some email and wondered if I forgot to eat lunch again.
3) Does your current role allow for flexible or remote working? If so, how does that fit into your life and routine?
Yes, which is great. I run my own speaking, writing, and podcasting business, and the team I’ve built for MSR is able to work from wherever, whenever, as long as we all get the job done.
The reason I’m an entrepreneur, in addition to wanting to help others and solve problems, is control. I want control over my time on this earth before I die. I get to do this once.
I don’t want someone telling me to be in certain places or do certain things if I disagree that they’re good uses of time. Entrepreneurship is at the same time generous to others (if you’re building something others need and want) and incredibly selfish.
4) Do you have any tips, tricks or shortcuts to help you manage your workload and schedule?
I am insanely organized inside of Evernote. It’s like my brain, outsourced. But I also rely on my calendar obsessively. If it’s not on there, it doesn’t get done.
This includes big blocks of uninterrupted time for deep work. We spend too much of our days at work slicing up our calendars into 30- and 60-minute increments.
Even worse, we’ve now taken any blocks that are free and stuffed them full of chat alerts, emails, and social media notifications. When are we supposed to think critically, be creative, and do good work? For this reason, MSR does not use an internal chat tool, and we try to bunch our meetings to certain days.
For me, that means Monday and Thursdays. Mondays are admin days, where I don’t worry about doing any sexy creative work. I’m just blowing through a checklist of back-end or administrative stuff.
Thursdays are generally free of travel, because my keynote speeches tend to happen Monday, Tuesday, or Wednesday, just given that I usually open or close events, which are normally not end-of-week affairs. So on Thursdays, I do my team 1:1s.
Secondarily, I also hold meetings strictly between 1:30 and 5pm unless it’s my team. By pushing meetings into the afternoon, I can prioritize the most important work early, when my brain is sharpest.
Third and lastly, we organize all our team knowledge, assets, and processes into Tettra, which is a lifesaver for me.
Basically, I want to compartmentalize and batch-execute administrative tasks, including meetings, document everything I can to remove it from my head and not worry about it, and keep my mind as clear and as focused as possible on the mentally and emotionally task of creating content that somehow, some way, cuts through the noise and resonates with others.
5) What does work-life balance mean to you and how do you work to achieve that goal?
If you’ve read anything about my work thus far, it will come as no shock to you to realize two things: (1) I adore my work, it feels like play, and so I don’t actually have other hobbies, and (2) I am terrible at work-life balance.
Look, this site reached out to me ostensibly because the owner admired my work, and for that, I’m ridiculously grateful and honored.
But truthfully, anyone who is doing incredible work and gets profiled publicly is outright lying to you if they say they have a job they’re obsessed with, a family to spend time with, and also a bunch of hobbies, mindfulness practices, gym routines, and books they read.
Yes. They are lying. They’re puffing out their chests, trying to claim publicly that they have it all. Make no mistake: They do not. They have bouts of getting all that stuff crammed into a week. But they have far more bouts of struggling to balance all of it and pursue a line of work that feels more like a vocation than a 9-to-5 job.
To me, work-life balance means constantly trying to course-correct. When you’re too far to the left, you find reason to tack back to the right a little. Hopefully that reason isn’t burnout or a fight with your spouse or a battle with mental or bodily health.
Like anything big and nuanced and messy and worthy, “work-life balance” isn’t a final destination. It’s a bunch of small choices made all the time as you constantly try to course-correct to find balance.
Anything else some “guru” says is just plain untrue.
6) What do you think are some of the best habits you’ve developed over the years to help you strive for success and balance?
Having my daughter 10 months ago. Literally nothing forces you to shut off work or helps you gain perspective quite like that.
Aside from that, I find that when I’m overly concerned work isn’t going well, I lose all semblance of balance. I need to manage my own psychological state as much as or even more than managing a “business.” I feel like most entrepreneurs or creators figure that out after a crisis.
I certainly did: I struggled with loneliness and burnout for about 12 months until I found a few ways to restore balance to my life. Partly, that was telling myself every day, “I get to do this work. I don’t have to do this work.”
Partly, that was remembering that ‘enough’ is a decision you make, not a destination you reach. Partly, it was the commitment to schedule face-to-face interactions (or at least more phone calls instead of texts and emails) with others who could enrich my life — former colleagues, new connections, industry peers, friends outside work, family members, and so on.
And honestly, the most useful thing in the world to remembering to be moment-oriented (which, to me, means balance)? Remembering that I’m going to die. Yup.
In fact, in Bhutan, they say that remembering you’re going to die five times per day actually increases happiness. Sounds morbid and backwards, but I believe it. I’ve felt it. In fact, I discovered that fact via an app called WeCroak, which sends you a reminder five times per day, at random, along with a quote about life. Sounds weird, I know, but it’s been incredibly effective for me.
7) Are there any books that have helped you improve over the years?
- The Essential Calvin and Hobbes: A Calvin and Hobbes Treasury (or any collection of Calvin and Hobbes, really) by Bill Watterson.
- Kitchen Confidential by my storytelling idol, Anthony Bourdain.
- Letters to a Young Poet by Rainer Maria Rilke (in various translations).
8) What is the number one thing you do to make sure you get the most out of your day?
Ensure that I’m being proactive. If I’m being reactive — which, I realize, is most people, especially most people working in larger corporations — I know I will create worse work, feel more stress, and generally not get the most of my day.
When you’re an entrepreneur, it’s surprising how soon your total control and proactive ways can turn into reactive work. When I worked at large organizations like Google and HubSpot, I thought that if I had an off day or week or month, the downside was dire.
Then I started my own business. Now, if I have an off day, the entire team or business can start down a bad path that takes weeks to recover from. If I have an off week, we can lose serious amounts of revenue. If I have a bad month, we might close, which means I lose my job and others do too. To me, the stakes have never felt higher.
To ensure I get the most out of my day, I have to feel intrinsic motivation and joy in the process of doing the work, not worrying about the results, because if I do, I know we’ll get better results.
This ensures I’m proactive. I’m not panic-hopping between trends or emails, nor am I reacting to requests or external pressures.
I’m doing the hard, humbling work to figure out the market, figure out what brings me and the team energy (and what drains us of energy), then I’m doing the three things every founder and leader is supposed to do: setting the vision, aligning the team, and ensuring we have enough money.
Sounds simple. It’s not. But it’s the most meaningful work I’ve ever done, and I wouldn’t trade it.
9) Do you have any last thoughts on work, life or balance that you’d like to share with our readers?
The moment you compare yourself to others is the moment you’ll start to derail. You’ll get stressed that you don’t have balance. You’ll get stressed that you’re stressed at not having balance.
You’ll get stressed that you’re stressed about being stressed that you don’t have balance. You’ll get further and further away. “Careers” are just a shorthand term we use to describe a lifelong process of self-improvement.
The last video game system I owned was Nintendo 64. If you ever played Mario Kart, you might remember that the lamest, least fun way to play was Time Trial. That’s where you’d pick a course and try to set your personal record for finishing it.
Play it a second time, and a ghost-like version of your past self would appear — a replay of your best-ever time on that course. Your job would then be to beat your past self.
That’s what we should do with our careers. Forget what everyone else is doing, and focus on beating our past selves. All this stuff really is, when you get right down to it, is a journey of constant self-improvement. It may have been pretty lame in Mario Kart, but it’s both effective and fulfilling in life.
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