Turns out I like being needed

It has been two months since I retired from Microsoft and, more broadly, from a technology career that spanned nearly 30 years. That is still a weird sentence to write.

Two months is not very long. It is certainly not enough time to offer some grand wisdom on retirement, how to do it right, or what I have figured out about the next chapter of life. I have figured out very little. But it is long enough for the initial feeling of being on an extended vacation to start wearing off, and long enough to notice some things.

Sunday nights are different

For most of my adult life, Sunday night had a certain feeling to it. I don’t think I ever had a particularly bad case of the “Sunday scaries,” but there was always a mental transition happening because Monday was coming. What meetings did I have? What did I forget to finish Friday? What problem was waiting for me? What was first on the calendar?

Sunday evening was when part of my brain started loading work back into memory.

That doesn’t happen anymore.

Sunday night is just…Sunday night. There is no Monday morning meeting, no inbox waiting for me, no calendar I need to mentally prepare myself for. It is wonderful, but also a little strange. When work has provided the rhythm of your weeks for essentially your entire adult life, removing it changes more than your calendar.

I’ve spent decades organizing life around work. Now I get to figure out what organizes life without it.

So what do I actually do all day?

This is probably the question I’ve been asked the most, and the answer is both “a lot” and “I’m not really sure.”

I’ve spent more time with family. I’ve been outside more. I’ve exercised, done projects around the house, handled errands at absurdly convenient times, and had appointments without doing calendar calculus to figure out where they fit between meetings. I’ve had lunches that didn’t need to end because someone had a 1:00. There is something pretty great about deciding to do something on a Tuesday morning simply because you can.

I’ve also had days where I look back and I’m not entirely sure what I accomplished. That part has taken some adjustment. For most of my life, productivity was easy to measure. There was always a list, a deliverable, a problem solved, a decision made, a person helped.

It turns out I’ve trained myself pretty well to believe a day needs an output.

I’m not sure I’m very good at unlearning that yet.

Shouldn’t I be doing more?

There’s another version of that same discomfort I didn’t expect.

For years I said some variation of, “If I only had more time…” Well, now I have more time. A lot more of it.

So why am I not traveling constantly? Why haven’t I booked all those trips? The world is my oyster, so why am I sitting at home on a random Wednesday?

There is a weird pressure that comes with having complete control over your time. You spend years wishing you had more of it, and when you finally do, suddenly there’s this obligation to make sure you don’t waste it. I can catch myself wondering whether I’m somehow failing at retirement by not maximizing retirement.

Which sounds ridiculous as soon as I write it down.

I spent a long time optimizing work, schedules, finances, and time. It would be pretty easy to turn around and start optimizing retirement too. Maybe having freedom doesn’t mean I have to consume all of it immediately. Maybe not every empty square on the calendar needs to be filled simply because the squares are finally mine.

I’m still figuring this one out.

Retirement wasn’t a spontaneous decision

One thing I don’t want to gloss over is the part that actually made all of this possible.

I retired from Microsoft on a particular day, but preparing for retirement didn’t start that day or even that year. It took years of thinking intentionally about what we wanted our future to look like and, just as importantly, talking about it together.

My wife and I had to be aligned on what we wanted. What would “enough” look like? What were we willing to change? What weren’t we willing to change? What did we want retirement to enable for us and our family? Those conversations happened over years, not weeks.

We also sought professional advice. I’m reasonably comfortable with numbers, spreadsheets, and obsessing over scenarios, but that doesn’t make me a financial professional. We asked questions, modeled different outcomes, and tried to understand the risks rather than simply hoping everything would work out.

One lesson I’d offer anyone thinking about their own future is to make every dollar work as hard as it reasonably can. That doesn’t have to mean complicated investment strategies. Sometimes it is incredibly boring.

Cash is an easy example. If you have money sitting around that you don’t immediately need, know what it is earning. A traditional checking or savings account might pay essentially nothing while a high-yield savings account can pay meaningfully more for doing exactly the same thing: sitting there.

I realize I’m not exactly revealing the secrets of Wall Street here.

That’s sort of the point.

Small, boring decisions matter. Pay attention to where your money is, what it costs you, and what it earns. Start earlier than you think you need to, communicate with the people you’re building a life with, and seek advice from people who know more than you do.

A shout out here to my friend James Montemagno, who built My FIRE Number, a great set of tools for exploring financial independence scenarios. A calculator isn’t a financial plan and someone else’s FIRE number isn’t yours, but putting numbers around “someday” can help turn it into an actual conversation.

For us, the goal was never simply to stop working as early as possible. It was to create the option. Eventually the question changed from “Could I retire?” to “If we can do this, do I actually want to?”

That was a much more interesting question.

Turns out I liked being needed

This has probably been the most surprising part.

I’ve always believed your job shouldn’t define you. I’ve given that advice to other people. I’ve written versions of it here before. Back in 2013, I wrote about priorities, passion, employment, and work-life balance and admitted pretty plainly that I worked too much.

At the time I was wrestling with priorities, family, career growth, and the realization that making different choices might mean I wouldn’t know everything happening around me professionally.

Apparently I was foreshadowing something.

What I didn’t fully appreciate then was how much validation work provides. For nearly 30 years, there were signals almost every day telling me that I was useful. Someone wanted my opinion, needed help with a problem, valued some experience I had, or thought I might be able to make something better.

There is ego wrapped up in that whether we like to admit it or not. I was useful to people, and work told me so constantly.

Then one day I retired and that faucet basically turned off.

My wife and I have discussed this, and I have explained to her that Microsoft previously employed thousands of people who collectively provided the validation necessary to sustain my self-esteem. She has not yet agreed to take on the additional workload.

I may need to establish some SLAs.

Joking aside, this has been a real adjustment. There is a difference between knowing intellectually that your job is not your identity and actually removing the job. For a long time, being useful was almost automatic.

Now I have to think differently about what useful means.

Nobody needs me to keep up anymore

I still see the barrage of technology news, especially in AI. New models, new tools, new announcements, new products, and a steady stream of things people insist will change everything.

For almost 30 years, seeing that kind of news triggered an automatic response: I should understand this.

There was also always somebody around to talk about it with. People at work, friends in tech, people building things. Somebody else had seen the same news and wanted to dissect it.

Now I see something new and interesting and my wife doesn’t care.

To be clear, this may be the healthier response.

I can explain that some new model just did something that would have seemed impossible a year ago, and she can respond with a perfectly reasonable, “Okay.”

And that’s it.

Nobody is waiting for me to have an opinion. Nobody needs me to understand it before tomorrow. For the first time in a long time, I have to decide for myself whether this deserves three hours of my attention.

Should I care this much?

That’s a harder question than I expected.

There is absolutely a part of me that worries I’m being left behind faster than I thought I would be. Of course I am. I retired. The technology industry, somewhat rudely, did not.

But I’m starting to realize that my curiosity and my professional insecurity may have been intertwined for a very long time. When I see something new and immediately think, “I need to understand that,” I’m trying to ask myself something else.

Do I actually want to understand it?

Or do I just want to know that I still could?

Those aren’t the same thing.

Thirteen years ago I worried that changing my priorities might mean knowing less professionally. I can now confirm that completely stepping away is a very effective way to accomplish that.

Turns out I’m not entirely comfortable with it yet.

Parenting when time isn’t the excuse

One of the reasons retirement made sense for me was family. For years, one of the easiest things to wish for was more time. More time with my wife, more time with my kids, more flexibility, more ability to say yes.

Now I have it.

And, somewhat inconsiderately, everyone else has continued having their own lives. My kids did not reorganize their schedules around my retirement. Apparently this was not part of the agreement.

I’ve also discovered that having more time does not necessarily mean I should use all of it to help.

My daughter has been going through some genuinely challenging things, and my instinct as a parent is to help. More specifically, my instinct is to solve. I have time now. Lots of it. I can research the problem, find people to talk to, develop options, make a plan, and figure out the next five steps.

I can research the hell out of almost anything now.

And sometimes that’s exactly the wrong thing to do.

My wife and I have talked a lot about how sometimes our job is simply to listen, be compassionate, and wait until help is actually asked for. That is much harder than it sounds when you have both the instinct and the available time to solve the problem.

For most of my career the pattern was fairly straightforward: problem, investigate, develop options, solve, feel useful. Parenting doesn’t always work that way, especially as your kids get older.

Sometimes being useful means resisting the urge to prove that you are useful.

I’m still learning that one too.

Finding a new tribe

Retirement also happened at the same time as a move, which meant leaving behind some of my closest friends.

They’re still my friends, of course. We text, talk, and stay connected. Distance doesn’t erase any of that, but it does change the shape of a friendship. There is no “want to grab lunch?” No “let’s ride Saturday morning.” No assumption that if you don’t catch up today you’ll probably see each other Wednesday anyway.

I miss that more than I expected.

Something wonderful has happened too, though. We call each other more. Actual phone calls and actual conversations. When you can’t count on the Wednesday meetup, you have to be more intentional. Some of those conversations have been longer and deeper because we’re not assuming we’ll just pick things up again in a couple of days.

I love that part.

What I miss is the spontaneity. The friends I left behind became close friends through years of rides, dinners, trips, jokes, difficult moments, random conversations, and a thousand other small things. There is no shortcut for history, and you can’t manufacture it in two months.

So now I’m trying to find a new tribe in a new place, which is weird when you’re older. You have to show up, introduce yourself, be the new person, and eventually make that slightly awkward transition from “person I see around” to “person I might actually call and ask if they want to do something.”

Cycling helps. Community helps. Showing up helps.

But I still wish sometimes that my best friends were close enough to text, “Ride Saturday?” and have that be the entire plan.

Finding places to be useful

I’ve found myself thinking more about causes and community and places where I might contribute. I’d like to believe this is driven entirely by a noble desire to give back, but I’m self-aware enough to know there is probably some “please find me useful” mixed in there too.

That’s okay.

For most of my career, usefulness was attached to expertise. I knew something. I’d seen something before. I could help solve a particular kind of problem.

Maybe part of what comes next is learning that usefulness doesn’t always require expertise. Sometimes it might just require showing up, caring, and having the time to help.

I have some of that now.

Two months is not a conclusion

I don’t have a neat conclusion to any of this, which feels appropriate because it has only been two months.

And just to be clear, I’m fine.

More than fine, really. I’m enjoying having control over my time. I’m spending more of it with my family. I’m outside more. I’m exercising more. I have choices that I spent years making intentional decisions to create.

I also recognize the privilege in even being able to write a post wondering what to do with all my free time. I had a long and fortunate career, we planned for this for years, and I have a partner who was part of every one of those decisions. A lot of people don’t have the option to just decide they’re done working, and I don’t take for granted that I did. So none of this is meant as “woe is me, I have too much time.” If anything, I’m realizing that I spent years preparing for retirement financially and almost no time preparing for it emotionally.

It’s just weird.

I spent nearly 30 years knowing roughly what I was supposed to be doing on a Monday morning. I knew how to measure whether I was productive. I knew how to be useful. I knew why I needed to keep learning the next thing. A surprising amount of validation came bundled with all of that.

Now I get to decide which of those instincts I want to keep and which ones I can let go.

I don’t think I want another job right now. I also suspect I’ll eventually find more things to fill some of the dead time. Maybe that is helping with causes I care about. Maybe it is building something because I actually want to rather than because somebody needs it. Maybe it is travel, more riding, new people, or something I haven’t even thought of yet.

I’m trying not to be in too much of a hurry to figure it out.

Thirteen years ago I worried that prioritizing other parts of life might mean knowing less professionally. Well, I finally did it. I know less. People need my professional opinion less. The technology world is moving on without me exactly as it should.

And I’m okay. I’m just still figuring out what comes next.

For now, it’s Sunday night. Tomorrow is Monday, and for the first time in essentially my entire adult life, that doesn’t require anything from me.

It’s wonderful.

It’s also still a little weird.