July 10, 2025: Never have I ever had a “real job”… until three weeks ago. It’s simultaneously completely crazy and totally normal. This is the full story… well, part of the story. Today I fly to Kilimanjaro and I want to publish this before leaving. Work has been full speed, so I haven’t been able to dedicate as much to this story as I wanted. So this is probably Part 1.

​About: Every week I write about living a great story: mostly personal stories, adventure recaps, links to coolness and analog photos that most likely have nothing to do with what you’re reading. They are random, but I love shooting film, so the photos are snippets of my photography craft.

Quote for the Week: "To see the world, things dangerous to come to, to see behind walls, draw closer, to find each other, and to feel. That is the purpose of life." LIFE Magazine from the movie The Secret Life of Walter Mitty.

Read time: 9 min

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The long journey of deciding to get a job

“I’ve never had a real job” - me, so many times, proud of my decade+ entrepreneurial journey.

To clarify, I’ve had jobs. In high school, I worked at a bakery, waking up at 5:30am Saturday/Sunday to sling delicious pastries. After dropping out of college, I worked at a canoe and kayak shop that was nowhere near the water. It was terrible and I suffered there way longer than I should have, but learned lots of life lessons. Next was lululemon for 9 months. Then I got fired because I was late to work a few too many times. That’s what they told me, but in reality, I didn’t buy into their work culture cult, so they wanted me out. My last job was in 2014 at a craft cocktail bar in San Diego. This job funded my life while I first started building LIVE A GREAT STORY.

I don’t consider any of those “real jobs”. They were short-term gigs with no real career escalation, a means to support myself and figure out my life as a college dropout trying to build a business. To me, a “real job” means a career job that develops a specific skill over an extended period, one that I could earn promotions, raises, working my way up in the world. A boss who had a boss who had a boss. Clocking in, working late, playing the W2 game, building a resume, 401k savings, full benefits. To me, that’s how I’ve thought about a “real job” my whole life. (I realize the definition of jobs is different for everyone).

Way back, right after returning from traveling in 2013, I was committed to getting a real job. I definitely didn’t want to start a business because every “business” (6?) I had started since high school had… failed? Did they ever really start? But coming back from traveling, running out of money, and moving to a new city, I knew I needed (and also wanted) a real job. So I bought a digital course called “Dream Job” and set out on my first attempt at landing a real job, most likely in marketing, probably at an agency or small business. The job search was cut short when I found an interim job as the door guy at the cocktail bar (definitely not marketing) and eventually stumbling into LIVE A GREAT STORY. I never found that real job.

Over the course of my ten solid years with LIVE A GREAT STORY, I considered going back into the work force often. Maybe two or three times I almost did it. Like in 2014 when I took an online “dream job” course that helped me figure out that marketing and branding was my path, so I started applying to marketing agencies. Or like in 2018 when I launched a successful/failed Kickstarter that put me in the red for a third of my current yearly salary. Or in 2019, after digging myself out of that hole, getting into an even bigger hole, learning the tried and true lesson that revenue ≠ profit. Or in 2022, when I announced to social media that I was committed to getting a job, but only half-heartedly started on the journey. Then in 2024, after embarking on a massive LIVE A GREAT STORY rebrand / relaunch that didn’t quite work as planned, I realized that it was time to for-real for-real step away from full-time entrepreneurship and find a “real job”.

But what does finding a real job even mean? I’ve never really looked for a job before. How do I start? What do I do? How does this job thing work?

The (dreaded) “Job Search” begins

I quickly realized that finding a job is not a linear process. It’s confusing, pathless, there’s no proven approach, and it’s filled with lots of trial and error, dead ends, and uncertainty. Very similar to entrepreneurship, where I’ve lived for basically my whole life, so this feeling wasn’t unfamiliar. Still weird, though, mainly because I was playing a new game.

Like Michael Jordan jumping from basketball to baseball: successful, gifted, skilled… but it’s a new game. There’s an adoption curve of learning new rules, lacing up new shoes, wearing a new jersey, new scoreboard. I knew in theory it would be a different game but suiting up and hitting the field hits different.

“I’ve never played this game, so I have to learn the rules, kind of, but also I’m going to make my own rules” is how I approached it. Sometimes there’s power in not knowing how something is supposed to be done, like this story:

At the beginning of the year, I hoped for a six-month timeline to find a role. I was confident about my experience, relaxed that I had enough of a buffer to not need to find something ASAP, understanding that I was in a new game, curious about the process. I knew my Tanzania trip was in July, so I was hoping to land a gig in April, give it a solid couple of months, take a trip, then return back to a job.

I started strong in January, tapered in February because I was basically traveling all month (Guatemala/Colombia), jumped back in heavy in March and April, then faltered in May when I should have been cranking up.

On a scale of 1-10, I would give my job search a 7.

Here’s what I did and didn’t do:

• Resume update specific to a marketing strategist role

• LinkedIn refresh and a commitment to posting a lot, for the first time

  • I turned off Instagram all year, so I found my creative outlet on LinkedIn. I started posting a lot, “talking trash” is what I called it. New platform with new rules but I just did what I wanted, saying what I wanted, how I wanted it. The resounding “be yourself, it’s what sells right now” is strong across the internet, so that’s exactly what I did and it felt great. This definitely helped me in the hiring process.

• Lots of clicking. So much scrolling. Being off Instagram, surfing LinkedIn and X and all of the job platforms and websites felt like a waste of time. I would find a job or company, browse their website, stalk their leadership, look at their social medias and on and on. Hours would go by like this, leaving me questioning if this was truly productive or a faux-productive waste of time. Overall, I found it necessary.

• I researched a lot of the “job world” that I didn’t know existed, learning about new industries, business models, trends in the workforce, how job titles work and all sorts of specifics of employer/employee details. It was fascinating because I’ve always been on the outside of this world, so it was interesting to learn more about a part of life that I knew very little about.

• I asked for “help from network” but this was a weird one because how do you actually do that, at scale, without feeling needy? I could have done a better one-to-one here but really I gave it a half-hearted effort. Also, just because of the incredible volume jobs and job variety, to me it felt like the likelihood that someone had access to the role I was searching for felt slim.

• I almost always applied to roles through the compani’s website, not on LinkedIn or Indeed. I figured it was better to go straight to the source rather than a proxy.

• Stalked tf out of the business, potential connections, history and everything I could find. In multiple interviews, I was told, “Wow you really did a lot of research.”

• My recruiter friend helped a ton with my understanding of all parts of the job search process. As a newbie, it was super helpful having an expert to answer questions about interviews, bounce strategy, give advice. Highly suggest this type of person. Knowing what I know now, I might consider hiring a job coach for this type of support.

• Hardly any “in-person networking”. Even though Austin is a top-tier destination for business, I met no one in real life. I should have and I would have liked it, but I just didn’t. A side effect of broader life changes happening this year (relationship/friends).

“WTF I have a job now… and it’s so… normal… and I’m loving it"

Here’s what I journaled after my first week:

Sitting here typing this after my first three weeks, I feel the same. I was in the office probably 50 hrs/week. Counting all of the extra mental space committed to problem solving outside the office, I dedicated 55+ hrs/week to this new role… and it feels great. I’m energized, creatively stimulated and ambitious in my goals. The team is great and I like being in-office for the first time in my life. I’m looking forward to coming back after my trip to keep building on the momentum.

It’s crazy to say that. I don’t know if I would have thought I’d feel like this. When approaching this new phase, I hoped I would feel like this. It was the goal. And now I’m in it, it feels great. But then I realize “I’ve never been here before and had no idea what getting a job would be like and I’ve stayed away for so long.” What a contrast.

“What’s the job??”

I am now the Paid Marketing Specialist at selfpublishing.com. I was hired to build and scale their paid media strategy which means designing, producing, launching paid multichannel paid ads.

In the first three two weeks I scripted, filmed, edited 20+ videos to launch a full overhaul their Meta ads account. We’re going to scale this to the moon and in the process help a bunch of bad ass business owners write books that grow their businesses.

Well, this is definitely Pt. 1

Lucia and I leave for the airport in a few hours. We’ve been at the coffee shop for two hours getting in some last minute computer work. Still need to fully finalize packing. But I wanted to get this out. Feels good, but incomplete. More thoughts to share, more of the story, more of the role. Check for Pt. 2 eventually.

A preview of coming newsletters:

• [NEXT WEEK] Scenes from Tanzania, Pt 1. I leave for Africa on Friday to host a group trip to a Serengeti Safari, summit of Mt. Kilimanjaro and some R&R at Zanzibar beaches. Next week’s email will probably be a quick recap of the 30 hour trip, Moshi / coffee tour / waterfall and some reflections about going back to East Africa for my third time.

• I said “hi” to my sister’s newborn baby. Sunday, I said “bye” to my grandmother, with a kiss on the forehead and tears streaming down from my cheeks. Sitting with my grandmother on her deathbed revealed a new understanding about life, a missing link in the equation of what I thought it meant to live a great story. [AUGUST]

• Two years ago I found myself nearly stranded in downtown Nairobi, Kenya. The bus dropped me off in the downtown bus station well after sunset. No phone service. No accommodations. No plan. Not a good idea. So I went with my best choice and accepted the invitation to stay with the supposed pastor I had just met on the bus. Last week, he just sent me this photo of a bootleg, knockoff LIVE A GREAT STORY shirt. This week, he sent a dozen. This is a continually developing story, can’t wait to share it with you. [AUGUST]

I’m off to Africa, back to Tanzania for my third time. Stoked af. Three weeks full adventure mode. Serengeti safari > Mt. Kilimanjaro > Zanzibar… all with my favorite person! (and five strangers about to be real good friends).

Thanks for tuning in. If you dig this, please share with someone who might also dig it.

See you next week,

-z

P.S. I’m raising money for a life-saving ambulance for my friend’s village in Kilimanjaro. We’re close to hitting our goal, please consider donating here.