Stepping out of the shower this morning, I realized that I was in the middle of a midlife crisis.

Tortoise Totem

Like most things with me, it came on very slowly. Years ago, I identified the tortoise as my spirit animal, as s-l-o-w appears to be my preferred pace in just about everything. My midlife crisis cooperated with my totemic self-conception in languidly creeping up on me. Like the proverbial frog in the pot of water gradually brought to a boil, I didn’t notice what was going on until the bubbles started to pop.

Actually, the trite boiled frog simile doesn’t fit. I’ve carelessly mixed aquatic animal analogies. Unlike the frog—who has the ability to jump out of the hot water at any moment if only it would become aware of the danger—responding as a tortoise, the most I could expect was a s-l-o-w paddle toward safety. On the plus side, I guess I could draw on that thick, protective shell the frog lacks, and perhaps a bit of the tortoise’s fabled wisdom, so perhaps chances for survival of stewing are even or better.

My midlife crisis began, as I’m sure it does for many, with the onset of milestone birthdays. When I turned 40, I had the anxiety-inducing thought, “Wow. If actuarial tables are to be trusted, I’m roughly halfway through my life expectancy. Am I making good use of my limited time?” As a Douglas Adams fan, I passed another milestone birthday at 42. Unfortunately, I can’t say that the age brought me the answer to life, the universe, and everything—just more angst-inducing existential questions. And because I find the symmetry of palindromes pleasing (or in this case, portentous), looking forward to birthday number 44 as I write these words feels like another ominous milestone looming on the horizon…

But days pass faster than my tortoise-pace lets me react to them: Between writing those few paragraphs and beginning this one, another year has passed and I have just turned 45! I am still simmering in the existential stew, though I have at least been steadily paddling. Unfortunately, while I have picked a direction, it’s not yet clear to me that my efforts haven’t just taken me in circles.

Enough of noting years whizzing by at their frenzied pace and back to the story of my slow-motion midlife crisis. As an introvert, I’ve always been something of a navel-gazer, but these midlife milestones sparked in me more serious soul-searching and reflection. What was I doing with my life? What purpose did it serve? What difference was I making? These hard questions insistently presented themselves to me. Easy answers to them did not.

At the same time, I had fragments swimming around in my head that I thought might be able catch and assemble into a meaningful reply to my self-interrogation. These included: long-unfulfilled entrepreneurial ambitions dating from my 20s (now half my lifetime ago…); a desire to be a producer, not just a consumer; to create something that provided value to others; to do so at scale rather than just in the small organizational contexts in which my professional efforts had previously bounded… These unfulfilled aspirations addressed those existential questions in such a way as to allow me to turn anxiety into energy, to shape a midlife crisis into an entrepreneurial (ad)venture.

The opportunity to embark came when my wife landed a job with salary and benefits that did not require me to bring in a full-time professional income to maintain our standard of living. That new job required a move from Chicagoland to Boston in summer 2013. I spent the first months getting us settled in our new home while consulting part-time. As I worked on move-in projects around the house, I listened to podcasts or audiobooks, as is my habit when performing solitary chores.

A few months in, I happened to listen to Harvard Medical professor Atul Gawande’s The Checklist Manifesto, a book extolling, with compelling examples, the merits of the humble checklist. As a process-oriented person—a long time member of the American Society for Quality and Six Sigma Green Belt who had spent years building out detailed procedures in previous jobs—his lauding of the checklist resonated deeply with me. Given my previous experience trying to integrate standard operating procedures into organizational workflow, The Checklist Manifesto triggered an idea for a web + mobile app that I soon became obsessed with pursuing. That pursuit was my own midlife manifesto, a goal I deemed worthy enough to pursue as at least a partial answer to those troubling questions asking what I was doing with my life that justified my existence.

And so, TaskTrain was born. (Or, more precisely, after 107 other product names were generated, evaluated, and discarded, TaskTrain was born…) I won’t belabor the details of my pet entrepreneurial project. It’s not that the idea itself is so great that it has that enormous significance in itself—I’m not ending world hunger or curing cancer—but the challenge of starting my own business, of seeing an idea from conception to birth and, with luck, to maturity, was a use of my time and talents that would stretch me, tapping unfulfilled potential and generating missing meaning in the process.

Challenge and stretch me it did (and continues to do). There were many aspects of the entrepreneurial undertaking that I was and am pretty good at: Product design, prototyping, technical specifications, business model generation, project planning (well, at least work breakdown structures, if not duration estimation), and rudimentary marketing all were things I could do myself competently, some quite well. But there’s always too much to do in a startup—especially when one is foolish enough to start as a “solopreneur”—and there were many aspects I was not very good at, some not at all. Actually coding the product was (at least at the start, if not now) beyond my college coding course competence. Cold-calling potential customers and wooing partners offended my introvert sensibilities. Major marketing required design execution skills I completely lacked. And building a team from scratch to fill in those major gaps in my own skills meant building my own self-confidence and skills of persuasion far beyond their previous levels.

Oh, and while I’m excellent at task decomposition, I’m not good at estimating task difficulty and time. In fact, I’m really bad at that one. Apparently I have big-time optimism bias and fall for the planning fallacy every time. What I thought would be a part-time 18-24 month launch—perhaps 6-month build, one-year sales ramp-up—has turned into 4+ years of building, with us just now (in time for birthday #46) having a product close to being sales-worthy. Satisfactorily enumerating the reasons it’s taken so long would be its own blog post (or, better yet, Harvard Business Review case study of what not to do when starting a startup), but suffice it to say that even with an MBA with a concentration in entrepreneurship and a decent range of relevant skills, as a first time entrepreneur, I didn’t know what I was doing and wasn’t good at much of what needed to be done.

On the plus side, the daily humbling confrontations with my limitations engendered by the pursuit of my startup ambition generated a whole set of new anxieties that supplanted the existential questions that sparked the entrepreneurial adventure in the first place: How am I ever going to build this thing? Will I ever make any money again? What kind of job can I get when this thing fails? As someone with an over-active fear of embarrassment (doubtless one reason I tend to be so process-oriented and obsessed with “getting things right”), I’ve spent my entire life working in my areas of competence and carefully avoiding failure. This project was putting me in contact with my limitations and incompetence on a daily basis, so these questions were almost more painful (and certainly harder to avoid) than the nagging but nebulous existential questions that spurred me on this path in the first place.

Still, I was committed to capitalize on the amazing opportunity I had in the arrangement my wife and I worked out which allowed me the freedom to pursue these entrepreneurial ambitions. The flexibility to not work full time was a great gift, one I happily exchanged for taking on the bulk of the household chores to maintain some semblance of domestic tranquility as a refuge from her demanding job and my own stumbling attempts to turn my business idea into a profitable reality. I continued to take on a few part-time consulting engagements and eventually (after some home renovations opened up extra bedrooms) play Airbnb host in order to make some modest financial contribution to the household. But these obligations still left me largely in control of my time, allowing me to pursue TaskTrain as I chose to prioritize it.

However, as time passed and daily failure piled upon daily failure with no clear signs of progress, the freedom granted by this seemingly idyllic arrangement provided me with precisely enough rope to hang myself. To prevent that from literally happening, I cast about for ways to deal with the new anxiety-activating questions that came piling on top of the old anxiety-activating questions …

Increasing my consumption of wine in the evenings was one quite effective answer to those nagging questions. After a few glasses, such troubling questions simply didn’t arise. Anxiety gone! In the fuzzy-headed dawn, however, my wise totem tortoise would inform me that drinking like a fish was, of course, actually counterproductive. Recognizing the long-term folly of that short-term fix, I kept on the hunt for less self-defeating coping mechanisms, drawing ideas from positive psychology audiobooks and podcasts I added to and drained from my iPhone media queue.

One of those mechanisms was reflective writing like this blog post, which was born out of a personal journal entry. I had experimented with daily journaling off and on in the past with good effect during periods of emotional turmoil but I had not made it a regular habit. My newfound control of my schedule made it easier to re-engage with the practice. (Well, should have made it easier to do so. Although I had control of my time, I still needed to control my attention, which is a very different challenge.)

But when I did manage to gain control of my attention, I found that spending even a few minutes with my morning cup of coffee making my thoughts visible on the screen, regardless of whether they happened to be lucid or disordered, was a helpful practice. If I was feeling anxious, writing out those negative thoughts acted as cognitive behavioral therapy and helped me clearly see the often unfounded assumptions behind the unpleasant emotions these thoughts created. Seeing the holes in my thinking lessened my anxiety, at least enough to let me get started on another day undistracted by troubling thoughts of doom. Likewise, if I was stuck on a how to solve some problem, writing it out would give me a way to clarify the question and work through some potential answers during a morning session or two. And if I was actually feeling OK—which, looking back on my entries, had an odd correlation with journaling on a sunny morning—then I would respond to one of a set of prompts, such as articulating my personal mission/essential intent, reflecting on a favorite quotation, responding to a meaningful question, or expressing gratitude for the many gifts in my life—any of which would usually boost my mood and bolster my motivation.

A second practice I committed myself to was regular mindfulness meditation. I’ve been drawn to the psychological and philosophical (though not religious) teachings of Buddhism since my early 20s. Throughout the ensuing the years, I’ve followed with interest the stream of studies demonstrating salutary effects of its core practice of meditation. I had the intention of regularly meditating for a decade or more prior to this midlife crisis, but only rarely had the discipline to maintain a daily practice for more than a few days in a row for a few weeks a stretch. But with greater control of my time, I renewed my commitment to sitting on the floor and staring at a basket for short period every morning.

I can’t say that 10 minutes of daily zazen (sitting meditation) over a few years has brought me satori (sudden Enlightenment), but, consistent with my tortoise pace, it has been a gradually enlightening practice. What I have learned is that my mind is very good at seeing things that aren’t there: detecting faces in the weave of the basket that happens to be in my view during meditation sessions, for example; but also fictive scenarios playing out my mind even while I just sit and breathe. These mental fantasies seize my attention even though in the moment they have no more reality than those imagined faces. Just watching my thoughts while I follow my breath has been instructive in understanding how much I project onto the external world and how frequently I torture myself by becoming immersed in imaginary scenarios not present in my actual immediate experience.

Sometimes I can even recognize such mental patterns when I’m not sitting on a cushion on the floor staring at a basket. It’s still hit-or-miss, but I am slowly becoming more consistent in catching myself before hopping on a train of negative thoughts as they roll unbidden into my consciousness. When I am able to watch them pulling in and recognize them before they take hold of me emotionally, I can much more easily choose to remain on the platform, waiting for them to steam out and be replaced by the next train of (perhaps more useful) thoughts, allowing me to not have my consciousness hijacked by these phantoms quite so often or for so quite long.
Such mindfulness is quite helpful when attempting to defuse the fear and anxiety generated by losing my attention to those self-doubting questions I enumerated earlier. If I’m honest, though, I must concede that the same insight that such negative doubts are—at least in the moment—empty thought-phantoms also applies to the positive fantasies I entertain: Any success I may secure, entrepreneurial and otherwise, will not be an ultimately satisfying answer to the existential questions that such achievement is intended to address. Those speculative outcomes have exactly as much meaning as I choose to place on them; Their value lies in the extent to which they lead me to act in a way that allows me and others to flourish more fully moment to moment.

A surer and more practical support of such personal wellbeing comes from the third practice I’ve cultivated—daily physical exercise. In keeping with my incrementalist approach, I don’t push myself very far or very fast. Instead, I just strive for consistency—getting some aerobic and/or strength exercise for at least 15 minutes each day. Frequently, I can double this up with some household chore that needs to be done, such as mowing the lawn with our manual reel lawn mower, which turns into 45-60 minutes of walking against resistance. In the opposite season, shoveling out from the latest Nor’easter intermittently provides a suitably intense aerobic workout. My favorite such double-duty chore is the “exercise errand” of bicycling the 11.6 mile round trip to Trader Joe’s for our weekly groceries, which I fit into two large pannier bags clipped to the rack on my Trek Soho Deluxe. On those days when the weather doesn’t cooperate and/or the heavy household work is finished, I bring my heart rate up with a brief burst of 25 burpees and then slowly lift and lower dumbbells while trying to smarten up by watching technical tutorials.

Regular exercise, meditation, and journaling have been beneficial consequences of my midlife crisis. To be honest, though, I’m certainly nowhere near 100% compliant on any of them. I let my mornings get derailed quite frequently such that nearly every day one or more of them doesn’t happen. However, I’ve still managed to hold on to each of them consistently enough to consider them habits. Take this rambling entry as proof of at least some measure of adherence to my least consistent custom of journaling. While I’m not as unwavering as I’d like to be, I’m a paragon of practice when compared to my pre-crisis self.

That’s all well, but I still have a long way to go. Those three practices help start my day well, but the second law of thermodynamics guarantees that things can still go wrong many more ways than they can go right during the remainder, especially when I’m putting so much time into my startup, which, like any, is a highly uncertain, likely-to-fail venture. In an attempt to retain any equanimity my morning practices may grant me in dealing with such vicissitudes, I’ve also mapped out a set of routines to insert into the remainder of my day. Specifically: taking an intentional break after work to plan the next day and transition to evening activities; taking stock of the day before going to bed, reflectively recording a daily appreciation (gratitude), apperception (lesson learned), aspiration (goal for tomorrow), & accountability (to yesterday’s aspiration). However, anchoring these evening and nighttime habits has been much more challenging than establishing those three morning practices. I very rarely end the day as strongly as I started it. Is it possible to close a day with a sense of satisfaction and feeling of gratitude that matches my morning optimism in its promise? Further strengthening my morning foundation and building supportive structures into the rest of my day are my next challenges.

Even with my struggles and middling progress toward mastery, I believe that I’m on the path to make the most of my midlife crisis. The difficult questions with which I confronted myself spurred me to begin the professional challenge of re-skilling mid-career to start a company. Whether or not it’s financially successful, I deem it a worthy (ad)venture that I know I would have regretted not attempting. To cope with the stressors of this self-created crucible, I’ve managed to initiate and maintain a few personally nurturing practices which I think serve me well. Most days, these allow me to alchemize my anxiety into productive action.

So I continue my tortoise-like paddle toward progress, welcoming whatever wisdom I fathom along the way, in the hope that I’m (slowly) heading in the direction of making the second half of my life even better than the first…