When the Worst Case Scenario is Not Synonymous with the Worst Life: Interview with Writer and Entrepreneur, Alex Michael

This week’s interview is with Alex Michael. Alex has embraced a life that is wonderfully multifaceted. He is the writer of the substack blog, “A Questionable Life” (which I highly encourage reading), as well as an entrepreneur. Alex owns the e-commerce wallet business, Wallaroo, and is building a new product for the lacrosse industry via a venture called NoKnot Lacrosse. In addition, he has an incredibly cool side gig booking guests for David Perell’s podcast How I Write.

Alex’s path to this point was not linear. Like many of us post college, he chased careers based on a desire for status and prestige. In 2017, several years into his career, he hit an emotional rock bottom. He wasn’t happy. A period of soul led to a career pivot from consulting into sales. Alex says it was the first time he’d made a choice based on who he thought he was and what he was uniquely suited for. The more he traveled down that path, the more he realized his internal desire to become an entrepreneur. After years of searching for the right business, his offer to buy Wallaroo was accepted in 2022. Things were off to the races. Amidst Alex’s efforts to spur growth, the business surpassed $1 million in revenue during his first year of owning the business. However, crisis struck in mid-2023 when Amazon unexpectedly lost one-third of his best selling inventory. Having to order more inventory ahead of schedule, being out of stock during critical moments, and the algorithmic punishment that ensued for going out of stock led to a perfect storm of events that forced Alex to declare Chapter 11 bankruptcy for the business.

I was compelled to reach out to Alex because of who he was and who he has been amidst the “worst case scenario.” In a post on his blog called “Fixing in Public,” Alex contends, “Today, all I have is fear, uncertainty, and the threat of insolvency. This has objectively been one of the most challenging experiences of my life. But in many ways my existence has felt easier, or at least more optimistic, than five years ago. How could that be? The answer is that I’m living a life that is mine.” Alex has come out on the other side of the bankruptcy case. He continues to own and operate Wallaroo and engage in all the things that make his life and work so multifaceted. In a world where it’s all too easy to not pursue what we want based on the fear of failure and what might go wrong, I believe that Alex’s story invites us to consider what the worst case scenario really is and the power that agency creates in our lives…even amidst crisis.

Note: The following interview has been lightly edited for clarity and length. While every effort has been made to preserve the integrity of the conversation, please be aware that the quotes may not be verbatim but reflect the essence of the dialogue.

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How would you describe the things you currently do for work?

The word “tentacles” comes to mind. I've got a lot of tentacles going at the moment. Some currently reach further than others. I've got my core passion project that I've been working on for going on four years now that will hopefully last at least another four years, which is a lacrosse business that I'm building with a couple of partners. We’re working on a product that we hope is going to solve a big equipment problem in the sport. It has not generated a single dollar, and it may not ever generate a single dollar, but I really love working on it. That’s number one because it’s nearest and dearest to my heart.

I also have a contract freelance role where I try to get the best authors in the world onto my favorite podcast which is called “How I Write,” and it's done by a guy named David Perell. A very fortuitous series of events led to me taking that particular role. It’s a ton of fun. Outside of that, I've got a number of other things going. I do freelance writing work, as well as my own writing. I also have a wallet e-commerce business that I acquired a few years ago, which I'm sure we'll get into.

You’ve spoken and written about spending the first few years of your career post college chasing money, status, and prestige - things that would impress other people. You got to a point where you realized that you were miserable and started doing a lot of exploration around who you were and what you were uniquely suited for. That led to a career change into sales and eventually to becoming an entrepreneur when you acquired Wallaroo. What do you think the most important shifts you made during that period were? What helped you get clear on what you wanted?

It’s hard for those shifts to come softly. They don't just sort of naturally, organically emerge without at least some local minimum. I definitely had one of those moments in 2017. It just felt like this big, emotional rock bottom and one of those inflection points where I thought, “If I don't have an entire paradigm shift in how I'm seeing the world, shit's gonna go even more south than it already has.” It became really clear to me that I had been living my life for other people, like a lot of us do during our early twenties. I’d optimized for outsourcing my life in every way; my financial well-being, my emotional well-being, all these different things.

The first big pivot I made was taking a sales job. You can hear the sarcasm in someone thinking, “Oh, cool! You took a sales job. What a big pivot dude!” But it was a big departure for me because I’d shifted from making a decision based on what would sound the most prestigious to other people, and picking jobs with titles like “consultant” or “investment analyst,” to actually trying to map who I really am to what I was doing for work. It was the first time I wasn’t mapping based on some idea of who I thought I should be.

You do that mapping and eventually take a big swing when you buy Wallaroo. After investing in growth and building Wallaroo to over $1 million in revenue during your first year of owning the business, Amazon unexpectedly lost three months of inventory of your best selling products. This led to a chain of events that forced you to file chapter 11 bankruptcy for the business. In a post called “Fixing in Public”, you said this:

“My operating philosophy over the past few years has been that agency and self-sovereignty are the most important qualities we can cultivate in ourselves. My belief has been that when we develop a deep, genuine understanding of who we are and what we want and then learn to give ourselves permission to pursue that path, we show up as the best version of ourselves in the world and can fully engage with it…But it’s easy to justify a belief system when things are going well. I wrote a lot about the transformative power of these ideas when the business was growing and life was relatively easy. Now that I’m confronted with crisis, it’s a perfect time to ask: does my belief system hold up? Well, I’m staring down the barrel of bankruptcy with no idea what comes next, and I have a better quality of life than I did when my bank account and 401(k) had big numbers with lots of zeros after them. So I’d say that’s a yes.”

How has that perspective changed how you view fear and failure over the past few years (if at all)?

I remember having that moment when it was all happening. I thought, “Okay, the worst case scenario is happening. This scenario that I never thought was even remotely feasible, even though I knew intellectually it was possible. I've spouted off about how great it is to be agentic and live your own life. How does that hold up to this pressure test of living through the worst case scenario?” I took a step back and thought about it. Financially it was insane. I didn't know what was going to happen with the business, and it was incredibly scary. Despite all of that, there was just a different texture of existence when I was navigating my own ship. I think there's an interesting distinction to be made here because I talk a lot about agency, and I think that can be falsely conflated with control or imposing your will onto the world. There's so much of our lives that we have no control over. It might be the whole thing we have no control over. But there's something about that feeling of authorship over your life that changes everything, and I think that paradoxically allows you to release your grip on the tiller.

I wonder if this will resonate with you. Failing at something that was your choice feels different than failing at something you didn’t choose.

Yes, exactly. A lot of life is about choosing what problems you want to have because you're gonna have a lot of problems. That's the nature of existence. But if you can opt into those problems and be more intentional about the ones that you want to end up with, maybe life will be a little bit better.

On the Better Work podcast, you shared that making agentic decisions created a virtuous cycle of action and feeling that compounded upon itself. Once you left your job and bought Wallaroo, you started making lots of other changes in your life like writing your blog and becoming an EMT. You said, “I had this emotional response to those decisions that said I’m the kind of person that makes those decisions and goes after what I want.” How did that mentality serve you in the period after declaring chapter 11 and navigating what would come next?

There are moments when everything goes wrong, and you go into scarcity mode and revert back to a previous version of yourself. It’s the feeling of, “Oh, God! Everything's screwed. Nothing I've learned is relevant anymore.” I don't think that will ever fully go away. The benefit of getting older is that you know yourself more, have more experiences, and diversify your life so that you can recognize that knee-jerk, fear response when it happens. Once I let that feeling settle and saw it for what it was, I realized that I had lots of collateral and evidence supporting the idea that I was someone who can make things happen because that's what I'd done. I had all this stuff to point to in my life, not necessarily from the perspective of “I’m so great” but more from the perspective that I'm capable. I realized that I wasn’t completely screwed. That gave me a sense of trust in the future. I remember talking to my girlfriend at the time and saying, “I have no reason to be optimistic or trusting of the future right now. All signs point to more calamity, but somehow I do.” And sure enough, something materialized. I, of course, took steps to make it happen, but it also felt like it fortuitously emerged. I think there's something to be said for having trust that in the final analysis things are going to work themselves out. To answer your question, I think that virtuous cycle of building up my agency muscle and crafting that identity set a precedent for being able to weather future storms.

We’ve mentioned your writing, and I would love to talk more about your style and approach. You embrace a lot of vulnerability in your writing and have written about your choice to write about “open wounds” rather than the more common approach of writing about “scars” that come after a writer has taken the time to process them. What do you think has motivated you to embrace vulnerability more and more?

I am curious about what’s made me be more vulnerable because I don’t think I was when I first started writing. It took time to open up those wounds and go deeper. I’d noticed that the work that resonated with me the most were the pieces where people really cut themselves open, not for the sake of trauma porn, but for the sake of showing what the human experience is. I always appreciated when I would read something, and then I felt less alone. I was really compelled to be more vulnerable so that I could do that for other people.

Writing is also how I process my experience in the world and metabolize what happens to me. I'm not a journaler for whatever reason. I process in public. What makes me keep doing it more and more is that so much good has come from being vulnerable in my writing. I can't tell you how much I've gained. And I don't just mean in a material sense. I mean in a sense of connection to myself and others. I don't advocate telling everybody your deepest, darkest secrets just for the hell of it, but there's a lot to be said for intentional vulnerability.

I’d love to see you play coach for a second. Given the experience you’ve had with opening up and being vulnerable, what advice would you give to someone who is paralyzed by the fear of what others might think about them?

I don't know if you've seen that Tim Ferriss exercise of fear setting, but I think playing something out to its logical end is always a good exercise. In the exercise, you really indulge the fear and play it out to the worst possible outcome. Shining a light on the thing can be really helpful.

I keep hammering this agency thing, and it feels like I'm beating a dead horse, but I think it's really important because the fear of what others think never goes away fully. However, it became less primary for me once I started shaping my own life in a way that suited me better. It created an emotional foundation that gave me more of a buffer against the fears of what other people might think of me.

Productivity is a common topic that comes up in my coaching sessions with entrepreneurs. You’ve written about how productivity is less about mastering the perfect systems, time blocking, and optimizing your calendar, and more about confronting the fear of uncertainty, embarrassment, and even failure. In the essay, “A Productive Panda,” you write:

“I’m reminded that when we examine productivity through the lens of the whole person—messy, irrational emotions and all—we begin to access the true productive power of humanity…We access our innate ability to work on the right things, the right way. Accessing this ability has made all the difference for me. It has allowed me to enjoy the life of a giant panda: a delightfully lazy existence punctuated by periods of working on what matters most.”

What helps you embrace the messiness rather than trying to fight it with a desire for perfect systems and “optimized” time management?

It’s funny that we continue to clamor aggressively for productivity systems in an attempt to seek control over the world when there is so much evidence that A) it makes us crazy and B) it doesn't work. I think I’ve learned to embrace the messiness because when I pay attention to the experience in my body when I try to ward off the big, scary villain of all the things I have to do, by way of pomodoro timers or whatever productivity bull shit I’m using, it just feels wrong.

I got really lucky with my parents. I have two parents who are very different and very smart in different ways. My dad always used to say, “Don't confuse activity with productivity,” which is very much in the vein of what we're talking about. My mom is very emotionally intelligent. I think those voices came together in how I view productivity because I learned to not confuse motion with movement and to recognize the emotional problem we’re actually trying to solve for. We often use productivity to ward off the demon of whatever feeling that we don't want to feel. I embrace the messiness mostly by remembering that. I still screw up all the time and waste time on things that aren’t important, but it's good to see that for what it is.

How has your relationship to self doubt changed over the past few years, if at all? What shifts or tools have you found most impactful in moving through periods of self doubt?

I've been thinking about that one a fair bit lately because it never goes away. I think trying to conquer things like self-doubt or the fear of uncertainty will eat you alive. The journey is in learning to dance with those things rather than try to outrun or kill them. You can apply that to any undesirable emotion you want, but I think my relationship with doubt now is something along the lines of “Oh, there's that thing again. How's it going?”

You’re clearly a big believer in living a life that reflects the fullest expression of who you are. What role do you think work plays in you living your own life to the fullest expression of who you are? (I was intrigued by the dialogue you had at the end of your interview on the Better Work podcast).

I think the host of that podcast, Ryan, articulated it really well. He thought about it in terms of a spectrum. On one hand, you've got Alex Michael the investment analyst or whatever it was I was doing early in my career that was so far removed from anything I should have been doing. On the other end of the spectrum is my writing, which is perhaps the purest expression of who I am. I think that’s a useful way to look at it because I think the more that we can get work to fall on the side of the spectrum that's closer to that purest expression, even if it's not the purest, we’ll have a better experience of living.

Many people I interview for the No Directions blog have created lives that are uniquely theirs in terms of how they live, work, and build their lives. What does the life that is uniquely yours look like today?

I'm a spontaneous decision maker, and I kind of just like to see where life takes me. Right now it's taking me to a place of a little bit more stability here in Richmond, which is exciting to sink my teeth back into. Something that's been really calling to me for a while is physical community.

No directions is a great name because I have no directionality with any of this. There’s a line from the book The Lion Tracker’s Guide to Life where the author, Boyd Varty, writes, “I don’t know where I’m going, but I know how to get there.” I think that embodies what we’re talking about. I'm gonna continue to operate and live, notice the signals that come up, nibble at them, and see what happens.

What’s next for you?

It’s an interesting question right now because I’m being pulled between two competing forces. On one hand, there's so much I want to do and learn, and so many things that I'm curious about. On the other hand, there's a lot to be said for having slack in your life. I’ve really enjoyed the seasons where I have that slack like I do now. I have no idea what's next. I'm saying it out loud that I’m open. I'm just gonna keep seeing what happens, writing, talking to interesting people like you, and I’ll see where that takes me.