I Don’t Need a Bigger Life. I Want a More Deliberate One.

Every once in a while, usually when I’m thinking about money, work, or my family, a sentence quietly runs through my mind:

I have something to lose now.

I don’t say it very often. Sometimes I’ll say it to one of my closest friends when they genuinely ask how I’m doing. Most of the time, though, I say it to myself.

What’s strange is that, financially, I’ve been in much worse situations. About eighteen years ago, after losing a business, our home, cars, and other assets, my family and I owed nearly $400,000. I was earning about $1,200 a month. We had barely $1,000 in the bank. It took a decade to recover.

Today, my debt is barely 15 percent of what it was then, yet today’s debt bothers me more.

By some measures, the past two years have been among the least successful of my adult life. I left Axelerant after nearly thirteen years and haven’t been able to build the solid professional income I expected. I’ve applied for hundreds of jobs. I’ve tried businesses that didn’t work. I made one particularly stupid financial decision that I’m still paying for. I’ve taught English, gone back to school, taken part-time work, experimented, reconsidered, and repeatedly asked myself what to do next.

My family isn’t even in one place. My wife, Huan, and one of our children are in Taiwan. One teenager is here in Portland with me. My younger children, Jace and Drusus, are continuing their education in Mexico, a decision I agreed to with their mother, Peichi, and their stepfather.

From the outside, this doesn’t look much like the life I expected to be living two years ago.

Yet another truth sits uncomfortably beside all of that: I like the Michael of October 2026 more than the Michael of October 2024. I’m probably more confident and self-assured than I was then, and more willing to question myself. I’m better at checking my assumptions. I’m more conscious of my ego. I’m more aware of greed and how easily it can disguise itself as ambition, confidence, or opportunity. I’m clearer about the people I love, what money is for, and what kind of work I actually enjoy doing.

And I’m increasingly comfortable with the possibility that a successful life might be considerably smaller and quieter than the one I once imagined.

How can I feel like I’ve failed during the past two years and also believe I’ve become a better version of myself?

Maybe both are true.

The Man Who Could Always Start Over

For much of my adult life, I had good reason to believe I could recover from almost anything. Businesses disappeared. Money disappeared. Homes disappeared. Relationships changed or ended. Careers changed. Countries changed. At one point, my family and I were nearly $400,000 in debt. It took a decade to dig out.

After my marriage with Peichi ended, I felt lost. I spent more time on the road, including extended periods in Vietnam and Thailand, when I couldn’t afford to live in Portland, Maine. COVID made everything stranger; I got stuck in Taiwan, and it took nearly a year before I could see my children.

Eventually, life began coming back together. By 2022, I had Huan, friends, a life in Taiwan I enjoyed, good income, no debt, discretionary money, and professional credibility. Most importantly, I had freedom again. I had come through another difficult period and built another life.

I don’t remember consciously walking around thinking, I can overcome anything. It was more subtle than that. It was an assumption underneath everything else.

I could find work. I could connect with people. I could make money. I could adapt. If I lost something, I could rebuild. If I encountered something I didn’t understand, I was smart enough to figure it out. If something needed doing and I said I would do it, I did my best to get it done, and usually I tried to leave it better than I found it.

That confidence wasn’t imaginary. I had decades of evidence supporting it. But good evidence can still lead to an assumption that goes too far.

Somewhere along the way, perhaps I stopped believing I was resilient and started assuming recovery itself was almost guaranteed. I’ve recovered before; therefore, I’ll recover again. I’ve made money before; therefore, I can make money again. I’ve built successful things before; therefore, I can build another one. I’ve been valuable to organizations before; therefore, another organization will recognize my value.

The first half of each statement describes experience. The second predicts the future.

It has taken me a while to understand the difference.

That distinction also matters because I don’t want to rewrite my past to make the present look wiser than it is. I didn’t spend the first fifty years of my life unthinkingly chasing money, status, and titles and then suddenly discover relationships in my fifties. That would make a convenient story, but it wouldn’t be true.

The ideas behind what I now call #BeingMichael began taking shape about a decade ago. Around 2016, Mridula joined Axelerant as a life coach. At the time, one of the biggest problems in my life wasn’t professional. It was my relationship with Peichi.

We had been together for about seventeen years. What had once been a beautiful love story had become increasingly unhealthy. We struggled to talk with each other. The ways we tried to love each other increasingly seemed to hurt each other. I wanted to understand what to do.

Through conversations and exercises with Mridula, I began thinking more deliberately about my purpose, principles, and values. What actually matters to me? How do I want to behave? How do I want people to experience me? What kind of person do I want to be when circumstances aren’t going the way I want?

Those questions gradually became a framework for my life. That framework has changed many times since then, as it probably should, but the purpose underneath it has become increasingly simple:

Live fully by living deliberately.

At the time, I wasn’t trying to create a philosophy. I was trying to figure out my life. I even let go of professional photography, something I cared deeply about, to focus more attention on myself, my relationships, and my family.

I tried deliberately for several years to recover the relationship with Peichi. Eventually I realized something that can be incredibly difficult to accept when you love someone: I could change myself. I couldn’t choose for her.

I could communicate what I needed, listen, negotiate, adapt, explain, give space, and try harder. I could tell someone what I thought they should do, but increasingly I came to believe that wasn’t how I wanted relationships to work. The other person still gets to choose. They might choose something I like or something I don’t. They might say they want something and then never act on it. Their words and actions might not match. They might not change at all.

Eventually, I had to decide what to do with that reality.

That lesson changed how I think about relationships, but it also influenced how I think about leadership. It helped form ideas I later articulated through Sustainable Ownership: give people context, clarity, boundaries, and opportunity, then let them exercise judgment. Don’t build systems where everything depends on one person rescuing everyone else.

The principle applies to personal life too. You cannot own another person’s choices. Sometimes trying harder isn’t noble. Sometimes it is another form of refusing to accept reality.

My relationship with Peichi eventually ended. The relationship failed. We hurt each other. Our children were affected by the conflict between us, and that remains one of the parts I most wish had been different. But I don’t think everything from those years was a failure. I learned more clearly who I wanted to be. I learned that loving someone doesn’t give me ownership of them. I learned that sometimes being true to myself requires walking away from something I desperately wanted to save.

Effort matters. It just doesn’t create control.

When Starting Over Didn’t Work

By 2024, my life looked very different again. Huan and I had bought a house in Old Orchard Beach, Maine, with the idea that within a year or two we might establish ourselves there more fully. My teenager would be in high school, and my younger children would be nearby enough that we could see them much more often. After years of divorce, remarriage, travel, and living across countries, I could imagine something closer to a geographically connected family again.

Then, not long after buying the house, I spoke with Ankur at Axelerant. The company wasn’t doing well enough. Revenue was down, expenses needed to be reduced, and I was given roughly sixty days to create meaningful new revenue from my area or my role would end.

I did what I have often done: I doubled down.

One thing still bothers me about that period. I had reservations about the sales and marketing approach we were taking. I didn’t think it matched what we needed to sell. But a decade of history and trust was involved, and some of the people involved were specifically responsible for sales and marketing. Part of me essentially said, Do what they tell you.

So I did.

As the deadline approached, I became much more direct with Ankur about believing we needed a different approach. I saw more possibility in training people to use automation themselves rather than simply doing automation for them. Instead of becoming the technical expert everyone depended upon, perhaps we could help people become more capable themselves.

Some conversations began looking promising, but the clock ran out. After nearly thirteen years, I was gone. In practical terms, I was laid off.

Strangely, I wasn’t devastated.

I had severance, experience, relationships, and a professional reputation. I’d always known my time at Axelerant would eventually end. I tend to push organizations, and sometimes the direction I push isn’t the direction the organization wants to go. That’s okay.

I thought I’d take a little time, experiment, perhaps build a business, develop the training idea, or find another leadership role. I had started over before. I’d do it again.

If October 2024 Michael could have predicted the future, I think he would have expected a couple of months off followed by another software leadership position. I’d join another company and help it grow. I’d help improve its culture, build stronger relationships, increase revenue, improve team continuity, and perhaps help make it one of the best places to work.

That was the scale at which I understood professional contribution.

Then starting over didn’t work the way I expected.

Over the next several months, I experimented with businesses. One helped me realize that I didn’t particularly want to spend the next chapter of my life pushing technology. I still like technology and use it constantly. I’m fascinated by automation and artificial intelligence. But being interested in something doesn’t mean I want to make it my profession.

Another attempt taught me that a good product doesn’t matter very much if nobody knows it exists. That sounds obvious, but it feels different when it’s your product. Creating something is only part of building a business. Someone also has to build awareness, find customers, communicate value, build trust, and sell repeatedly.

Today’s organic social media environment can make that a job in itself. You can find yourself producing content constantly just to earn the opportunity to perform the work you actually wanted to do. I began asking myself a simple question: Do I actually want this life?

Increasingly, the answer was no.

A third business showed some possibility. It might even have worked. But as I looked more closely at what success would require and what it would probably produce, I realized I might spend enormous effort building something that kept me around survival income. Something working doesn’t automatically mean it is worth continuing.

Meanwhile, I was applying for jobs. Hundreds of them.

For roughly nine months, and especially across about six months of serious searching, I received almost no meaningful response. Maybe three interviews.

Something wasn’t working, and I didn’t know exactly why. Maybe it’s that I’m over fifty, and employers may see decades of experience and assume I’m overqualified, expensive, stuck in my ways, or unlikely to stay. How I presented myself might have been wrong; I definitely think now that my resumes could have been better.

The market could have been unusually difficult, and on top of that, my career history doesn’t fit neatly into a single role. Some jobs may have viewed me as too senior, while others may have wondered why someone with my background was applying.

And I probably carried some ego about what kinds of work I should be doing. I sometimes thought certain jobs were beneath me. Maybe that was greed. Maybe ego. Maybe an outdated understanding of my market value. Probably some mixture of all three.

What mattered was that the methods I’d trusted for decades stopped creating an expected result:

Work hard. Adapt. Use my experience. Connect with people. Create value. An opportunity will emerge.

For much of my life, that worked.

This time, it didn’t.

I couldn’t make the market respond simply because I believed I had something useful to offer.

Yet somewhere in the middle of it all, I began teaching English. Initially, it was income. Not high income, and certainly not the kind I’d previously earned in professional services. It was survival money, not thriving money.

Then something inconvenient happened.

I loved it.

I liked talking with students. I liked figuring out what was stopping someone from expressing an idea. I liked helping someone move from knowing English to actually using it. I went back to school and earned additional qualifications in ESL and business English. I taught one-to-one, groups, and classrooms, and gradually I noticed that I preferred one-to-one work.

A classroom can be enjoyable, and a group can be engaging, but a classroom inevitably moves toward some kind of median. There is material to cover, multiple learners with different needs, and limited time.

One-to-one is different. I can get to know the person, understand what they’re actually trying to accomplish, and work on their problem rather than the abstract problem people at their level are supposed to have.

Maybe they don’t improve dramatically. Maybe they never recognize how much I helped. That’s okay. I can still know that I helped that person become a little more capable.

That began changing my understanding of meaningful work.

In my professional life, impact had scale: growing a company, improving a culture, building a team, developing systems, increasing revenue, and helping hundreds of people.

Teaching reminded me that impact doesn’t have to scale to count.

This person needed something. I understood them. I helped. Something became better.

That’s enough.

Teaching didn’t solve my financial problem, and I don’t want to romanticize meaningful work that doesn’t pay enough to live. When someone who had followed my work approached me about becoming a Revenue Growth Director, I accepted. It wasn’t really the direction I wanted to go, and it brought me back to selling technology services, but it felt familiar. I knew the market. I needed income. The role was part-time, which also gave me space to continue exploring.

Sometimes deliberate living isn’t choosing between good and bad. It’s choosing among imperfect options.

Being Capable Doesn’t Make Me Immune to Being Stupid

One decision from these two years is one I genuinely regret.

I borrowed money to invest.

I had been working with algorithmic trading, and multiple early tests performed fantastically. That success told me a story I wanted to believe: money could make money. I understood what I was doing. I had found something that worked.

So why move slowly?

I took out a loan and invested the money. Within a week or two, I lost it.

Later, I had two accounts running the same algorithm. When the algorithm lost, both accounts lost. That shouldn’t be surprising. Same underlying strategy, same underlying risk. But optimism can make correlated risk feel like multiple opportunities.

I can call that decision confidence, risk-taking, optimism, or entrepreneurial thinking. But at least part of it was greed and ego. I’d made money before. I’d recovered before. The first test had worked. I thought I could accelerate the outcome.

I was wrong.

There isn’t a clever redemption hidden inside that. It was a bad decision. I’m still paying for it, and I would prefer that I hadn’t. Learning something from a mistake doesn’t retroactively make the mistake wise.

What I learned: moderation, downside protection, and patience matter if money is going to make money. However, a non-exciting lower-risk return can leave me considerably better off than chasing something brag-worthy. Ordinary earned income is worthwhile too.

Perhaps one of the uncomfortable lessons of getting older is discovering that being capable doesn’t make me immune to being stupid.

That mistake also helps explain why today’s relatively modest debt affects me so differently from the enormous debt I carried years ago. Partly, I don’t currently have the income to make it disappear quickly. But something deeper has changed too.

My relationship with money has become more directly connected to my relationships with people.

When I was with Peichi, I was often comfortable traveling on my own. Sometimes we traveled together, and sometimes I traveled alone. I enjoyed doing my own thing.

Over the past decade, I’ve realized how important a strong, meaningful relationship is to me.

It doesn’t always mean being physically beside someone. It means being able to talk about what’s happening in our lives, work through problems, and support each other the best we can. Sometimes with little more than quiet strength and a calm voice. It means loving someone for who they are, not what they’re doing for me.

With Huan, I’ve experienced something I don’t remember experiencing quite this way before:

For the first time in my life, I want to stay home.

I want to be next to her.

That makes separation feel different, and financial insecurity feels different too. If I don’t have enough money, I can’t easily travel to see my children. Their parents aren’t necessarily going to send them to visit me. If I want those relationships, I need to help maintain them, and that requires time, attention, and sometimes money.

I also want to provide a home.

My teenager is here in Portland, and I’m here because Huan and I deliberately made that choice. Huan and one of our kids are in Taiwan because of choices we made together. Jace and Drusus are in Mexico because I agreed to that choice with Peichi and their stepfather.

Right now, having everybody together isn’t actually possible. That doesn’t mean the family is broken. It means our family is living with the consequences of choices we’ve made across multiple relationships.

In another year, Kyle should finish university and may come to Oregon State University for his master’s program. Later, perhaps my younger children will want to return to the United States for school. If they do, I want them to have a place with me.

Money helps create those choices.

But underneath it is something simpler: I don’t particularly mind being poor. I’ve been poor. I can live simply. I can drive an old vehicle, live in a small apartment, and do without much stuff.

Being without love or the relationships that matter to me scares me considerably more than being without money.

That’s what I mean when I say I have something to lose.

A Smaller Scale of Ambition

Today, I’m living in Portland, Oregon, not Maine. I’m 54 and back in school studying microelectronics. I live in a modest one-bedroom apartment in an older building, drive a used Chrysler Pacifica, teach, study, apply for work, and go to the gym more because I haven’t been able to hike as much as I’d like.

None of this is particularly impressive as a professional announcement.

And I’m increasingly okay with that.

Returning to school has reminded me how much I enjoy learning when I can get close to something tangible. Two days of class can easily turn into another three days of reading, studying, researching, and trying to understand how the pieces interact. I’m not doing that because somebody told me to put in the hours. I want to understand it.

I don’t particularly want to be a manager right now. That surprises me a little. I can manage. I can lead teams. I’ve done it successfully and enjoy parts of it. But right now, I’m interested in getting closer to the work.

I want to know whether I can understand the system, troubleshoot it, hit the target, exceed it, take something basic and improve it. Can I learn something unfamiliar at 54 and become genuinely competent?

Those questions still carry ego. I won’t pretend otherwise. I still want to prove something to myself, and maybe to other people too.

I want an employer to look at me and not simply see someone older, overexperienced, or expensive. I might not be young and hungry, but I’m mature and hungry. I have led teams, but I’ve also picked up the phone, built systems, worked alongside people, put in the hours, hit numbers, and learned unfamiliar things.

I want to do that again.

What has changed is that I don’t particularly care whether doing it gives me an impressive title.

For a long time, I associated contribution with scale. That’s understandable given my career. If I could improve a system used by hundreds of people, that seemed more consequential than helping one. Improving an organization seemed bigger than improving one process. Developing a team seemed more significant than helping one individual.

I still believe that good systems and leadership matter. Organizations should help people do meaningful work without unnecessary dependency, confusion, burnout, or heroics.

I haven’t rejected any of that.

I’ve just stopped assuming I need to be at the center.

My teaching has helped me understand why. Give me one student and let me understand what they’re trying to accomplish. Let me identify what’s getting in the way and work on it with them. If they leave more capable than when we started, that matters.

The same could be true in technical work. One machine. One process. One problem. One person who needs help. Understand it, do the work, make something better.

I find that reduced scale increasingly appealing because I know who I’m helping and what we’re trying to accomplish. The feedback loop is shorter. There is less abstraction between effort and outcome.

This isn’t a rejection of ambition. I still want to be excellent. I still want to accomplish difficult things, learn, make good money, and leave things better than I found them.

What I’m questioning is whether ambition has to become bigger to become meaningful.

Maybe it can become more precise instead.

Less Certain, More Confident

When I say I think I’ve grown up during these two years, I need to be careful. I’m 54. Claiming I’ve finally figured out adulthood would be a little embarrassing.

I also don’t think the Michael of 2024 was somehow shallow and the Michael of 2026 enlightened. Many of the things I value today have been part of my thinking for years. I wrote about simplicity long ago. I cared about relationships, developing people, sustainable work, purpose, and values.

What’s different is that some of those beliefs have now been tested under conditions where following them costs more.

Maybe that’s what maturation has meant for me.

I’m less certain, yet somehow more confident.

Letting me better recognize that:

• I can be intelligent and still make a stupid decision.
• I can be experienced and still misunderstand a situation.
• I can work incredibly hard and still fail.
• I can create something valuable that nobody buys.
• I can be professionally respected and still struggle to get an interview.
• I can love someone and still need to leave.
• I can love someone deeply and be physically separated from them.
• I can be a capable provider and temporarily need my wife to provide more.
• I have decades of leadership experience, yet I want to be a beginner again.
• I can want more money without needing the most money.
• I can rest without being lazy.
• I can work hard without making exhaustion evidence of commitment.
• I can disagree with someone without needing to control their decision.

And I can be wrong without becoming worthless.

Those distinctions matter to me more today.

My current #BeingMichael framework tells me to separate facts from assumptions, interpretations, and preferences. Check assumptions, ego, greed, fear, the need for recognition, and the desire to be right. Consider impact alongside intent. Accept that I’ll sometimes be wrong. Learn, adjust, and move forward.

I haven’t mastered those ideas. They’re reminders precisely because I haven’t.

Sometimes I still doomscroll to read or watch short videos, even though I know I could be doing something more useful. Sometimes loss, frustration, self-pity, or something close to depression pulls my attention away from the present. Sometimes I choose to rest. Other times, if I’m being truthful, I’m escaping.

The difference matters.

Living deliberately isn’t maximizing productivity. I can’t sustain 100 percent effort. Nobody can. Sometimes the deliberate choice is to study or work. Sometimes it’s to go to the gym or call someone I love. Sometimes it’s to sit down and do absolutely nothing useful.

The point isn’t that every moment has to be productive.

The point is that, more often, the choice is mine.

That is also why I don’t think the last two years need a clean resolution.

When writing about difficult periods, there’s a temptation to make everything fit. The job loss becomes the blessing that opened the right door. The financial mistake becomes the lesson that eventually created wealth. Failed businesses become necessary steps toward the successful one. A broken relationship becomes preparation for the perfect relationship. The struggle becomes worthwhile because eventually everything works out.

I don’t believe that. At least not anymore.

Losing money doesn’t become a good decision because I learned from it. Applying for hundreds of jobs and barely receiving interviews isn’t secretly enjoyable because it taught me humility. Businesses that failed still failed. Relationships can leave damage even when we eventually become wiser.

And I don’t yet know what happens next professionally.

I’m still looking, studying, teaching, and considering opportunities. I’m still trying to establish sustainable income and benefits. I might end up working with microelectronics. I might find a role that combines technical work with my previous experience. I might return to consulting. I might eventually lead people again.

I don’t know.

And perhaps I don’t need to know yet.

I don’t need the next chapter to prove that leaving Axelerant was good. I don’t need a successful business to prove the failed businesses were worthwhile. I don’t need a six-figure salary to prove I’m still capable. I don’t need microelectronics to become my final career just because I’m studying it now, and I don’t need teaching to become my primary profession just because I discovered I love it.

These things can be what they are: experiences, capabilities, relationships, and choices. Some will continue. Some won’t. Some may combine in ways I can’t see yet.

That uncertainty used to feel more like a problem to solve.

I’m beginning to see it as a condition to live within.

What Enough Looks Like

A few years ago, if you’d asked me what professional success would look like at this age, I probably would have described something larger than what I want today. A leadership position. A strong salary. A growing organization. A company where I could influence culture. Maybe another business or another transformation.

Today, I can imagine never having another senior title, and I’m okay with that. I can imagine never founding another successful company. I’m okay with that too. I can imagine never earning more than $150,000 a year again.

That’s fine.

I don’t need a professional comeback story.

That doesn’t mean I’ve stopped caring about money. I want this debt gone and want to remain out of debt. I want to retire comfortably. I want health insurance and to be able to handle medical needs without fear. I want enough money for Huan and me to take a good trip together each year. I want enough flexibility to spend meaningful time with my children and help create a home where they know they can come if they need to. I want to invest sensibly, and I want normal financial decisions to stop carrying unnecessary anxiety.

I also want useful work. Work where I can prove to myself that I’m capable, continue learning, and see a reasonably clear connection between effort and outcome. Work that leaves enough of me available for the rest of my life.

Five years from now, I don’t particularly need a bigger house. I’m okay driving a used minivan and living in a small apartment in a fifty-year-old building.

• I want to be with Huan and stay close to my kids.
• I want more meals around a table where we’re talking, laughing, and enjoying being together instead of looking at our phones.
• I want to keep learning things that interest and challenge me.
• I want to stay active and move because I enjoy it.
• I want to keep looking at what I’ve done, admit when I’ve gotten something wrong, learn from it, and make better choices next time.
• I want enough money that I have choices, rather than money deciding what I can and can’t do.

When opportunities appear, I want the freedom to ask something more useful than Is this bigger?

I want to ask: Does this belong in the life I’m trying to live?

If the answer is yes, pursue it.

If the answer is no, perhaps let it go.

That feels increasingly like enough.

Living Fully by Living Deliberately

I started developing the ideas behind #BeingMichael a decade ago because I was trying to figure out how to live through a relationship that was falling apart. The words have changed many times since then and will probably change again, but the purpose has become simpler:

Live fully by living deliberately.

I used to think deliberate living was mostly about making good choices. Now I think it’s also about recognizing what I don’t control.

I can choose how hard I work, but I can’t guarantee someone hires me. I can create something useful, but I can’t guarantee anyone buys it. I can invest carefully, but I can’t eliminate risk. I can love my children, but I can’t choose where every one of them lives. I can love Huan, but I can’t guarantee that nothing will ever happen to our relationship. I can take care of my body, but I can’t stop myself from aging.

I can make plans, but that doesn’t mean life will follow them. I’ve learned to pay more attention to what’s actually happening instead of holding too tightly to what I expected.

For me, living deliberately means checking my assumptions and being honest when ego, greed, or wanting to be right is affecting my choices. It means working hard when the effort matters, but also recognizing when pushing harder won’t make something better. Sometimes I need to rest. Sometimes I need to change direction, admit I was wrong, let something go, or simply try again.

And keeping enough attention available for the people sitting beside me.

I still want a good job. I still want financial security. I still want to demonstrate that I’m capable. I still want to accomplish things.

There is nothing wrong with wanting those things.

I just don’t want them badly enough to trade away the things I’ve finally learned I value more.

The October 2024 Michael probably expected the next chapter to be another reinvention: another company, another leadership role, another opportunity to make something bigger and better.

Today’s October 2026 Michael wants something slightly different.

I want to do good work, help people, keep learning, and have enough.

I want a simpler, quieter life. And I want to go home.

Because now I have something to lose.

For a long time, that sentence frightened me. Maybe it should. Love creates vulnerability. Children create vulnerability. Partnership creates vulnerability. Caring about anything means accepting the possibility of losing it.

But “I have something to lose” tells me something else too.

It tells me what matters.

And once I know what I don’t want to lose, it may become easier to decide what is actually worth pursuing.