Time to retire?

Let’s say you’ve been working for a while and saving your money. Recently, you were laid off, reorg’d out of a role/team you liked, or you’re just not vibing with the new vibe-coding culture. Is it time to retire?

I retired six years ago after a 40-year career as a professional software engineer. I love being retired, but it was a big change. Many people I know tried to retire only to return to work a few years later. Others retire but spend their time watching TV, getting lost on the internet, or reliving the past instead of embracing the present.

A surprising challenge about retiring is establishing a new identity. Your former identity as a professional with a clear purpose, fancy title, and loaded calendar disappears, along with its sense of importance. You must create a new identity, purpose, and calendar for yourself. That sounds fun, and it is, but it’s also disorienting and deflating. How can you tell when you’re ready for this change? What can you do to prepare for a fantastic retirement? Relax into that front porch swing, and let’s make some plans.

Are you ready, Eddy?

Are you ready to retire? First, you need the resources to do so. Go into your checking account (or whatever you use for funds outflow) and download all your transactions over the last three years. Filter out all the money coming in, as well as the money you put into savings. Divide the remaining money by 3, and that’s how much you actually spend each year (plus another $20 – 40K/year for health care). Do you have enough passive income from investments and other sources to cover that amount, accounting for inflation, for as long as you expect to live? If not, you’ll need to reduce your actual costs and recalculate or bank more money.

If you’ve got enough passive income to retire, are you willing to give up your role and its importance? Maybe there are things you still want to accomplish. Maybe you can’t stand the thought of folks no longer taking you, your thoughts, and your decisions quite so seriously. If you’re not ready, then you should keep working and perhaps talk to a therapist, since one day you will need to let go.

If you’re ready financially and psychologically to retire, the only thing left is to have a plan for what to do with all that free time. You need a new purpose—let’s get you one.

What am I gonna do?

Many people imagine retirement as traveling the globe, taking cruises, and visiting friends and family. That sounds great, but a few years later, they’ll come home and have nothing to do.

Retirement isn’t an extended vacation; it’s a new phase of life. You’re going to need new reasons to get out of bed and do stuff.

Make a list of day-to-day activities that bring you joy and give you purpose. They could be hobbies, volunteer work, aspects of current or past jobs, sports, games, or activities you’ve always wanted to focus on but didn’t have the time. You should list five to ten things that each could take up three to five hours daily (ideally year-round), with several that involve personally connecting with others. My list included teaching, coaching, playing golf, playing bridge, listening to podcasts, reading, writing, contributing to open-source projects, and being a grandpa.

Once you have your list, come up with a weekly schedule for yourself. For me, I teach Wednesday nights at UW. I play golf on Tuesdays, Thursdays, and once on the weekends as weather permits. I coach underrepresented, midcareer software professionals weekdays when my calendar shows I’m available. And I fill the rest of my free time with podcasts, reading, writing, and open-source projects. (I don’t play bridge anymore because golf turned out to be so engaging, and I’m not a grandpa yet.)

Playing golf, listening to podcasts, and reading give me joy (and purpose at bettering myself). My teaching, coaching, writing, and open-source projects give me purpose (and joy). Those are more than enough to get me out of bed and look forward to my day.

Ch-ch-ch-ch-changes

You’ve got a retirement plan, but now you need to execute it. When and how do you start?

• First, check to see if any of your activities require preparation. Some prep is easy and can be done anytime, such as getting golf clubs or lessons. Some is more involved, like setting up a coaching business or engaging a local college to teach there. If any of your activities require significant preparation, and you want them ready when you retire, be sure to get that done in advance.
• Second, ensure the timing is right financially and in terms of health benefits. Do you have stock that’s about to vest? Are you approaching a milestone (such as turning 55 for vesting at Microsoft, or having your child turn 26 and no longer eligible under your health insurance)? Do you have other benefit needs that are easier to meet while still enjoying company-provided coverage?
• Third, transfer any personal documents, data, email, appointments, and contacts to your personal account(s). You should already be storing your personal information separately from your work information, but work and personal life inevitably get mixed up, so double-check that none of your personal information will get lost when you retire.
• Fourth, if possible, take advantage of any vacation days and other benefits before you leave. You get to keep your health benefits for 18 months after you retire (through COBRA), but the rest are “use them or lose them.”
• Finally, tell your boss that you plan to retire. If you’re open to being convinced to stay, you don’t need to mention a date. If your decision is final, specify a specific date that provides enough time for a smooth transition. If you think your manager will be a problem, cc HR on your notification and provide a specific date. (Be certain about your decision because once HR is involved, it becomes a reality.) As for a retirement party, let your manager know your preferences, and remember that it’s as much for your peers as it is for you.

What difference does it make?

If you’re like me and many other retirees I’ve spoken with, you’ll question what value playing golf, listening to podcasts, and reading provide society. A psychologist, a moralist, and your mom would tell you that every human being has intrinsic value, regardless of how they spend their time. On a practical level, I’m certainly not as productive or impactful in retirement as I was working full-time, and that’s okay.

I’m okay with being retired; not because I worked hard and saved for so many years. Not because I raised two sons to tax-paying adulthood. And not because things I’m doing now or things I’ve done before are making a lasting contribution to society. I’m okay with being retired because, at this point in my life, my relationships are the most valuable thing to me. Spending time with people and things I care about is now what makes me feel happy and fulfilled.

I’m free

Yes, I’m retired, and I love it. I’ve got enough passive income to cover my estimated expenses for as long as I expect to live. I’m okay with being a random retired dude instead of having the fancy title, responsibilities, and authority I used to have. I’ve got several different activities that bring me joy and purpose. I was well-prepared to retire and did so at the right time for me and my family. And at this point in my life, I feel fulfilled simply spending time with the people and things I care about.

When people ask me what I love most about being retired, I tell them that I’m doing exactly what I want to do every minute of every day. It’s the best, and when you’re ready, I hope you enjoy it as much as I do.

Aloha oe

This column marks the end of my 25^th year of publishing I.M. Wright’s “Hard Code.” Believe it or not, I’ve finally run out of the topics I kept in an Excel spreadsheet all these years. Perhaps I’ll think of more in the future, but being retired also means not encountering as much annoying fodder. So, this column will be the last of over 250 monthly posts, though I reserve the right to get pissed off at something and post about it here as a bonus. (For a list of my favorite columns, read a Fond farewell to Microsoft.)

I want to thank the numerous intelligent, generous, and forthright peer reviewers I’ve had over the years, many of whom I list at the end of columns they’ve enhanced. I’d also like to thank my many editors who’ve vastly improved the readability and professionalism of my columns, particularly my wife, who has edited and proofread my last 163 columns. Thank you, sweetie, you’re the best. Finally, I’d like to thank each of you for reading my columns all these years. This project helped me get through it all with my sanity intact. Did I mention how much I love retirement?