Questions for a Happier 2026

Not resolutions, but reflections on what actually mattered

This is my final post of 2025.

I want to start by saying thank you. Truly.Life in Rough Draft exists because you read, reply, reflect, and occasionally tell me that something here landed at the right moment. That quiet exchange—writer to reader—is what keeps this space alive.

If these essays have resonated with you this year, the simplest way to support this work is also the easiest: share a post with a friend, tap the ❤️, or restack it with a few words of your own. Those small gestures help these pieces find the people who might need them—and they let me know what’s connecting.

I’m looking forward to writing more in 2026, and even more to getting to know you better along the way—through comments, replies, and shared thoughts.

Thank you for being part of this ongoing draft.

See you in the next chapter.

—Og

I came across a recent New York Timesarticle by Jancee Dunn that proposed a deceptively simple question for reflection:

“What is worth remembering from 2025?”

Not milestones. Not accomplishments. But the moments that actually mattered —the ones that stayed with you long after they happened and quietly gave the year its shape.

Dunn shared a small ritual that ended up meaning more than she expected: every couple of weeks, she’d spend a few hours with her father while her mother was at a routine doctor’s appointment. He’d come over for lunch, they’d talk, eat, pass the time. Nothing remarkable on paper—yet those ordinary hours became a grounding rhythm, something that made the year feel fuller and more humane.

That framing stuck with me because it felt like an invitation to slow down and look at the year sideways—not through outputs, but through experience.

So I sat with a handful of questions she posed and answered them honestly, without trying to polish things up—very much stream-of-consciousness. What follows isn’t a comprehensive highlight reel of my 2025. It’s an attempt to notice what actually gave the year weight and texture.

When did you feel the most joyful and carefree?

At home, the answer surprised me by how simple it was.

This past year, my wife and I started a small tradition with our three daughters: weekly game nights. Scrabble, trivia, bingo for tiny prizes. Nothing fancy. But something about sitting around the table—ordering dinner chosen by the previous week’s winner, laughing, teasing each other in that affectionate way only close families can—slows time down.

Inside jokes were born during those nights. Silly moments turned into shared references that still come up weeks later. And I’ve become acutely aware of how precious that is, especially as my daughters grow older. One recently turned 24. Another will soon be 19. The youngest is almost 12.

I’m no longer the center of their universe—and that’s as it should be—but it means I’m more intentional about holding onto these moments while they’re still ours.

At work, joy showed up in a very specific way: when I was shoulder to shoulder with my teammates, deep in the trenches, solving hard problems together.

One moment stands out above all others. In March, I brought part of my team together for a week-long hackathon to build a prototype for a completely new project—one that would integrate deeply with our core product. For some of us, it was the first time meeting in person after years of working together remotely.

On the first day, we hit an unexpected wall: a public library we planned to build on had just been made private. Plans collapsed instantly. We had a choice—stall or adapt. We adapted. One teammate spun up a replacement library from scratch while the rest of us reworked our approach in parallel.

For four intense days, we operated like a tiny startup—long hours, shared meals, constant collaboration. On the fifth day, we presented a working prototype to senior stakeholders, and it landed. That week shaped the rest of our roadmap for the year.

My role during that time felt natural and energizing: connector, unblocker, decision-maker, cheerleader. I wasn’t managing from a distance. I was in it. That’s when work feels most alive to me.

What gave you energy—and what drained it?

In the second half of the year, I realized I’d gone far too long without a plan to stay physically active. Work had made me sedentary. So I joined a local gym that checked a few key boxes for me: an indoor track, an indoor pool, and plenty of parking.

Since my wife and youngest daughter leave for school by 7:30, I started going to the gym at 7:00. I’d work out for about 50 minutes—60 on Fridays—and be home by 8:00, with time to shower and mentally prepare for the day. That routine alone gave me a massive boost of energy that carried me through most mornings and early afternoons.

Another source of energy was planning small things to look forward to—tiny rewards scattered through the weeks. Sometimes it was going to a performance with my daughters. Other times it was grilling a steak and vegetables I’d bought earlier in the week for a special Friday dinner. Sometimes it was planning the next game night, or finding a way to make date night with my wife feel special. One evening, I surprised her with flowers and a battery-powered candle during a simple dinner. Small gestures, big returns.

What drained me most was workplace politics—especially situations where my autonomy or my team’s autonomy was suddenly curtailed by priority shifts or fire drills with no clear justification. I’m not opposed to pivots. Startups taught me that knowing when to pivot is a survival skill.

What I struggle with is change without clarity—no explanation, no definition of success or failure, no shared understanding.

If you’ve ever felt that shift—from trusted professional to interchangeable part—you know how quickly motivation drains.

What seemed impossible—but you did it anyway?

When I joined the gym in late August, I wasn’t sure I could maintain a daily morning routine. Waking up wasn’t the problem—I already wake up at six with my wife so we can have breakfast together. The challenge was getting myself out the door and fitting workouts around a globally distributed meeting schedule.

After some trial and error, I found a plan that worked. For the first 45 days, I went every morning without fail, alternating exercises and always coming home proud that I’d done something that once felt impossible.

Work-wise, I’ll be honest: I wasn’t sure I’d still be in my role by the end of the year. By last December, it felt like everything was stacked against my team. Some conversations with senior leaders left me uneasy about where things were headed. I even started quietly exploring other options.

One person at work helped me reframe what my role could be this year, and that shift directly led to many of the decisions I made—including the March hackathon. Looking back at what the team accomplished, and the obstacles we overcame, it truly feels like a mission impossible that somehow succeeded.

What habit, if practiced more consistently, would have a positive effect on your life?

Anyone who knows me knows I’m drawn to stoicism. I often recommend The Obstacle Is the Way by Ryan Holiday as an entry point. One of its core ideas is simple: don’t waste energy worrying about what’s outside your control.

Straightforward in theory. Hard in practice.

This year, I struggled with letting go—both at work and in personal relationships. Even when I knew something was beyond my control, I still felt compelled to intervene. If I could just say the right thing, maybe I could steer the outcome.

I know better. I still struggle.

The same applies to leadership.

Sometimes I care more about someone’s growth than they do. That doesn’t mean they lack motivation—it just means they may not be ready. And that has to be okay.

What did you try to control that was actually outside your control?

As a father of three daughters who are still growing and finding their way toward becoming independent women, it’s hard not to take it personally when advice I offer—especially around careers or important decisions—is brushed aside or dismissed. When you’ve accumulated experience, when you’ve made mistakes and learned from them the hard way, it’s difficult not to want to share that perspective with the people you love most.

The same dynamic shows up in my relationship with my wife, particularly when she’s navigating difficult situations or relationships at work. I don’t believe I’m an expert on all things career-related, and I certainly don’t think I have all the answers. If anything, I see myself as someone who is constantly learning, recalibrating, and realizing just how much there still is to understand. My intention is never to have people blindly follow my advice or obey my suggestions. That’s not what this is about.

The real struggle comes when I feel dismissed—not disagreed with, but dismissed outright.

And while that feeling isn’t the end of the world, it does sting. That said, I’m also self-aware enough to recognize the irony here. When I was 18, I was absolutely convinced I knew better than anyone—including my parents. I wanted to own my destiny, make my own decisions, and yes, my own mistakes. Through that lens, I can understand why my daughters might react the same way when faced with advice from someone who, in their eyes, has already lived a very different life.

Obviously, I can’t control how people react, behave, or decide. And I shouldn’t want to. That applies just as much to my wife as it does to my children.

There have been moments when I felt I could genuinely help my wife at work if she followed certain suggestions—lessons I learned through years of trial, error, and scar tissue. She listens patiently as I wax poetic about what I would do in her situation, but ultimately, those decisions are hers to make. And they should be. My role isn’t to dictate outcomes; it’s to be supportive, present, and available if she chooses to lean in.

I hope none of this comes across as me being overly opinionated or trying to control the people around me. I care deeply—about my family, about the people I work with, about those I invest my time and energy in. And because I care, it’s hard to watch people head down paths that, in my experience, may lead to unnecessary anxiety, friction, or pain.

Finding the balance is the real work here: staying caring without becoming controlling; offering guidance without attachment to the outcome; knowing when to speak and when to simply stay quiet and trust the other person’s process. I can’t want something more than they want it themselves. And as natural as that instinct may be, it’s one I have to keep checking—again and again. If you’re honest, where in your own life are you still gripping something that isn’t yours to carry?

Is there anyone you need to forgive in 2026?

Yes. This question lingers.

There are people close to my family who, over time, have stopped showing up in small but meaningful ways. Missed calls. Missed birthdays. Silence where connection once lived. I know life gets busy. I know people carry their own struggles. But repeated absence still hurts.

Forgiveness here doesn’t mean pretending it doesn’t matter. It means choosing not to let resentment calcify.

I also feel my patience thinning with leaders who hold positions of authority without vision, clarity, or values. I still have energy to give. What drains me is watching time and talent wasted in environments that exist only to “keep the lights on.”

Forgiveness here might look like letting go of expectations—and intentionally deciding where I invest myself next.

Looking ahead

As I think about 2026, I want to keep learning—technologies, ideas, stories. I want to keep writing: books, reflections, anything that keeps the words moving. I want to stay active without turning health into a competition.

I want more game nights, more date nights, more time with my parents. More small trips. More investing in the relationships that matter.

And looming over all of it is the question I can’t silence:

What is my reason for being—and how do I align what I love, what I’m good at, what the world needs, and what I can be paid for?

That question isn’t looking for a rushed answer. It’s asking for patience, honesty, and courage.

That may be the real work of 2026.

For now, I’m content to keep sitting with it—and if you are too, maybe the only thing to do is write the question down and let it follow you for a while.