Getting “Un-Stuck” in Work & Life

I used to be a serial over-analyzer. 

I had a knack for turning a tiny choice into an exhausting decision.

In the highway of life, I was getting stuck at every toll. 

But that soon changed when I discovered an alternative route. One filled with the same youthful bliss I’d experienced as a kid riding my bike down a steep hill. Pure joy.  

Coincidentally, it was at a charity bike event that I made this discovery. One that changed my life. 

But first, let’s back up to where it all began. 

You had to take two elevators to get to our office suite on the 63rd floor of a downtown Chicago skyscraper. On my first day, I remember thinking that was dope. But soon after I did some quick math. I then felt woozy when I realized I’d spend months of my life in those elevators if I worked there my whole career. Yikes. 

By 2018 I’d now been at the same financial software company for six years. Every six months since I started I got a pay bump and/or a promotion. Nice. 

Well, sort of nice. 

On the surface, the job seemed sexy. Cool office, publicly-traded company, financial software, etc…

But deep down, I knew I wasn’t becoming the best version of myself. And it was eating me up every night. Especially Sunday nights. Oh man, the Sunday scaries were real. 

It was my first job out of college and I felt trapped on a highway with bumper-to-bumper traffic. Each new team I joined, was me changing lanes and thinking, “hmm wonder where this goes?” I’d peek to the left to see how far the traffic was backed up. All the while thinking, “where does this highway even lead?” None of these routes felt right. 

Not only was I just learning to drive, I had no roadmap to know where I was going. Even worse, I had no idea where I wanted to go. I just knew I was driving in the wrong direction. 

I always had big dreams and ambitions for my career. Yet I never had actually defined them.   

I needed to pull over and recalibrate. Up until this point, I’d been on autopilot. Aimlessly driving with no destination in the GPS. I maybe had five vague ideas that sounded nice. But no clear destination.  

Turns out, if you input five destinations in the GPS it gets you nowhere. But if you input one destination, it shows you five ways to get there. 

It was time to pull over and figure out my next destination. 

“Un-Stuck” at Work

Around this time, I felt a calling to Austin, Texas. I’d heard great things. From the tech scene to the great weather and live music. It all sounded amazing. And I was ready to mix things up. I was enthralled by the thought of my new life in Austin. 

But I was equally nervous about the uncertainty. 

I remember thinking, is that what I’m supposed to do? Is my future wife down there? Or will a move to Austin completely throw off what the universe had in store for me in Chicago? 

Only one way to find out. I knew deep down I needed to make a change—and get off the highway. I also knew I didn’t want to regret anything later in life. So if I was being called to Austin, I needed to honor that. 

Shortly after this realization, I brought it up with my manager. We had an Austin office so I asked to do my role there. I was nervous and had no idea what he’d say. I actually had brought it up with a prior manager a year before and was turned down. 

But this time was different. I’d busted my buns for six years and made a decent name for myself in the company. 

I heard back the next week. “Good news, it was approved. Oh, and by the way, you’ll also get a relocation bonus. So we’ll pay for the move, flight, and a bonus.” 

What?! That’s amazing. Absolutely perfect. Or so I thought. 

It wasn’t until that moment I realized the true reason behind my urge to relocate. It wasn’t only to mix things up geographically but also professionally. Aka, a brand new job and likely a brand new industry. 

So after taking a step back, I knew it didn’t feel right to take the relocation bonus and move. Then just bounce to a different job. 

I also had a particularly exhausting week that week. I was pulled in a million directions and kept having people put meetings on my calendar. Sure maybe it was nice that people wanted me in the meeting to help them. But it was too much. I was in meetings or calls all day and feeling myself burn out. 

By that Friday I was wiped. I remember walking home thinking, I have to quit. I just have to quit. I was so sure I needed to, but yet so scared. 

What should I do? I kept playing out different scenarios in my head. Then I did what I always do when I’m stuck. I wrote out my thoughts. 

I created a new Evernote titled “Two Weeks”. The first few sentences helped me realize I needed to take action. The next section was then my game plan and how I’d communicate the two-week notice to my manager on Monday. 

Here’s the exact note. 

After writing out my thoughts, I quickly realized I didn’t want to keep saying “one day” or eventually. I pondered whether or not I was living the best version of myself. Apparently, my answer was, “NO, so fucking do something about it.” 

So I did. I wrote a quick outline of what I was going to say to my manager the following Monday. Then I soon went from a frantic mess to a calm relief. I knew it was right for me and I no longer was going to fight it. This lifted a gigantic weight off my shoulders. 

So Monday I quit. Two weeks later I moved to Austin. With no job. I told myself I was actively NOT going to look for a job for at least a month. I was on a mission to discover myself and the work I loved. 

I thought of this period much like the accounting term, zero-based budgeting. It doesn’t matter what last year’s budget was, with zero-based budgeting you start each new year from scratch. 

So that was my model, but with my life. It didn’t matter what job I had before or what I studied in school. I had from this moment until the end of my life. Everything else was a sunk cost. And I could now do ANYTHING I wanted. 

This foundation led to a magical period in my life. One month turned into two. And I was loving every minute of it. I was doing anything and everything I wanted. (See A New City.)

I worked out every morning. Then I’d meditate in the steam room for 20 minutes. After a quick breakfast, I’d walk down the street to the library. 

I read books, listened to podcasts, and went down any rabbit hole that interested me. I went to events and met new people. 

One event ended up being a job fair. Oops, had no idea. But it didn’t matter, I was making the most out of everything. I told them I was actually not looking for a job.  Sooo wtf was I doing at a job fair? I was just doing me. It was empowering. It felt amazing. 

So I kept going. Anything that looked interesting to me I would do it. 

• I went to a monthly Benjamin Franklin group discussing Franklin’s 12 virtues. 
• I went to a 512 meetup (Austin’s area code) and exercised in an open field at 5:12am. 
• I went to a poetry event and recited a poem I wrote on stage. 
• I did a 3 day fast. I almost passed out at one startup event from being light-headed. (Note to self: 3 days is a long fast.) 

I was quickly getting interested in online marketing and entrepreneurship. So I went to more events and met with entrepreneurs.

Tim Ferriss was speaking at one event I attended. His books and podcast have been a huge influence on my life, so I brought him a small gift. However, he left the event early.  

So naturally, I faked a phone call and left too. I chased him down in the parking lot nearby and gave him the “gift.” It was a sock coffee filter I heard him talk about once on a podcast. 

Why did I give Tim Ferriss a sock coffee filter? Because I had the idea and just did it. I was trusting my intuition and letting it take me ANYWHERE. 

Trusting actually isn’t the right word. I was honoring it. Getting out of my own way and letting my natural curiosity steer me in the right direction. The exact opposite of what I was doing in the corporate job.  

I went to more entrepreneurship and marketing events and joined a co-working space. Soon after, I started a marketing agency. I was learning a ton and loving it. 

By honoring my intuition, I was creating a new identity. 

As James Clear puts it, “Every action you take is a vote for the type of person you wish to become. No single instance will transform your beliefs, but as the votes build up, so does the evidence of your identity.”

Not all of my actions turned into something tangible. But each one was building my identity.  So I kept going and trusted it. That’s when things got interesting. 

One Saturday, I went to a “social impact summit” because it sounded epic. Philanthropy is an important part of my life so I wanted to create more space for it. I’d later volunteer with The Miracle Foundation and Code2College. Both founders I met at the summit. 

Shortly after, I also heard about a cool charity event from one of my favorite entrepreneurs and podcasters, Noah Kagan. He mentioned a Sumo Charity Bike ride. It sounded sweet, so I emailed him and asked if he needed sponsors for the event. 

He said yes. So I lined up a bunch. 17 to be exact. It was a good amount of work.  But I liked connecting with local businesses and I saw philanthropy as a core area of my life. Plus I started to get to know Noah. It was a win-win-win. 

I helped organize the whole event, including the silent auction. All the auction items (and booze) were donated. So we raised a ton of money and the event was a blast.  

Afterward, Noah asked if I wanted to join his company. Looking back this was a huge compliment. But I was focusing on growing my own company at the time. So I respectfully declined.

But a few months later, he hit me up again. This time with a different idea. He asked If I’d come work with him. Like directly with him, at the desk next to his. I’d help grow the podcast, newsletter, YouTube, etc. And I’d get a glimpse into how the software company AppSumo was running behind the scenes (it was growing fast). 

Gulp. I tried to play it cool. I wasn’t really even following everything he was saying. I just knew I liked it. 

This was another one of those moments where I just knew it was the right thing for me to do. So I followed it. 

I started part-time while I still had the agency. But it quickly went well, so I went full-time. 

I remembered back to those snowy Chicago winters where I’d bundle up for the commute and listen to Noah’s podcast. It was often the highlight of my day, igniting my curiosity and excitement.

Therefore, it was surreal that I now had the opportunity to literally work by his side. I took it and ran with it. I helped grow his content team and now I get to run another marketing team at AppSumo (which I’m SO pumped about, I’ll do another full post about it later). 

I now have worked with Noah for two years and learned the ins and outs of business, marketing, and entrepreneurship (highlights here). Like the real-life kind, not classroom theory. It’s been one of the best decisions of my life. And it was only possible because I created the space for it. I learned to trust and follow my intuition.

An “Un-Stuck” Life

This strategy was clearly unlocking something for me. I was “un-stuck” not only at work, but also in other areas of my life. 

The approach was simple. If I wanted to do something or if I was curious about something. I would JUST DO IT. That’s it. 

For example, if I saw a pretty girl I was interested in, I knew I had to just go talk to her. Yes, it’s scary sometimes. But that’s where the growth comes. And that’s where all the good stuff hides. Just right on the edge of our comfort zone. 

One time, I was at a bookstore. Why? I just felt like going one day. And I saw a gorgeous girl browsing the discounted books section (nice, she’s smart and likes a good deal too). I knew I had to talk to her, but I had no idea what to say. So I just said, “Find anything good over there?” She looked up and smiled. We chatted and I got her number. And went on an awesome 4-hour date later that week. 

Trusting our intuition in any single moment is where it starts. But it’s the compound effect of all these moments where the real magic happens. 

When we feel “stuck” inside or even “stuck” in traffic — it’s hard to know which direction to go.

But we can honor our intuition with one single action at a time. We push out of our comfort zones and get pulled into our natural curiosities.

A friend once told me about having a “frequency mentor”. Nothing formal, just someone you’re on the same wavelength as. I vibe with that. But maybe you don’t. That’s cool too. 

The key is just finding stuff you do vibe with. Find the people and things that resonate with you. The things that you might say, “ooh yeah that’s my JAM.” 

Don’t overthink it. Matter of fact, don’t think about it at all. Just feel it. Then do it.