It Takes More Than Money To Retire Early Interview: Randy

When we think about early retirement, we tend to focus on the money. That’s natural because we need money to retire early. Building up a portfolio is a crucial step to early retirement. When I was trying to retire early, it was all about how much we spend and how much passive income we need. However, it takes more than money to retire early.

We have done well over the years and saved up a good amount. That’s true for lots of people. There are over 11 million millionaire households in the US now. Most of these millionaires are still working hard. Clearly, money isn’t the only requirement for early retirement. Some people just aren’t a good fit for early retirement. Finance is a big part of the equation, but there is more to early retirement than that. I thought it’d be interesting to see what that elusive something is. That’s why I’m doing this interview series.

Randy retired a few years ago when he was 50 and he’s enjoying life. He has time to rediscover his passion. See what interesting projects he has been working on. Don’t miss this one!

Can you give us a brief background about yourself? What career did you retire from?

I was born and raised in the East Bay (of Northern California) and until retiring early, I lived most of my life in various parts of the San Francisco Bay Area.

After graduating from U.C. Berkeley, I spent several years bouncing around between various low-level jobs in media and the entertainment industry, including two years in Southern California. During this period, I was also involved in college radio, first as a movie critic and later as a writer, director, and producer of radio dramas (now known as audio theater in the podcast world). I also tried my hand at screenwriting. 

Eventually, I switched gears and got into tech. Not as part of any grand design, my main professional career turned out to be in Software Engineering (at various companies in San Francisco). I started as an HTML Developer in the mid- to late-1990s and eventually became a full-stack web application developer and people manager. In my last few years, I held Senior Manager and Director level positions.

I “FIREd” in mid-2018 at the age of 50. I left my job and moved with my wife and two kids (currently both in high school) out of the Bay Area. We now live close to the Sierra Foothills, where the cost of living is lower and the schools are great.

Early retirement means different things to different people. Lots of people don’t think I’m “retired” because I blog a few hours per day and I’m a stay-at-home dad. That’s perfectly fine. Everyone is entitled to their opinion. What does early retirement mean to you? Do you work at all?

For me, early retirement means being “work optional”. I wanted to achieve financial independence so that I wouldn’t have to work and would be able to control my time. Also, retirement meant getting out of the corporate world and leaving behind the daily grind of commuting, deadlines, meetings, etc.

Since retiring, I haven’t worked for money. However, I’ve been busy with my own creative projects. So, I’m “working” all the time — but for my own fulfillment as opposed to for money. Some of my projects eventually may yield some income, but I don’t need them to. 

Our FIRE plan also assumed that my wife would stop working. However, as we approached our FIRE date (and big move out of the Bay Area), she had a change of heart and decided to continue working.

What were your financial goals and how long did it take you to achieve them?

Until I got into tech, and eventually higher salaries, I wasn’t saving much. Basically, my twenties were a lost decade in terms of investing. After getting married in 2003, my wife and I started to amass considerable savings. Our double income tech salaries (and incentive stock options) forced us to get more serious about investing. In addition to maxing out our 401ks, we began to invest our excess savings in after-tax brokerage accounts. We eventually had enough savings to buy a starter condo townhouse and later to upgrade to a single-family home (both formidable challenges in the super costly Bay Area).

Working with our financial advisor of that time, we timidly defined a goal of retiring “early” by age 60. However, as our portfolio grew, we became more ambitious and started moving up our “finish line” to lower and lower target retirement ages. 

From the time we started retirement planning, it took about 13 to 14 years for me to retire early. One reason we could achieve the goal that quickly was that we had some good fortune with real estate. We bought our single-family home in 2009 and after the market recovered from the 2008 crash, our house appreciated substantially until we sold it in 2018. 

When I was planning my early retirement, I was consumed with the money part of it. I didn’t put much effort into the other details. I’d say it was 90/10, financial/non-financial. What about you? Did you put much effort into the non-financial side of early retirement planning?

I was similar to you. We focused our attention more on hitting our FI number than on what we’d do after. 

Once I started my career in software, got married, and had kids, I suspended all of my creative hobbies (and dreams). I did have the notion that I’d return to these passions sometime later in life, but that thought was vague at best. And I wasn’t sure I still had the creative spark in me.

Also, our kids would still be in middle school at the time of our early retirement target. So, I knew that family responsibilities would consume a fair amount of my time. One motivator for us was to be less stressed out parents — and to better support our kids with our time.

Funnily enough, it wasn’t until early in the year I retired that I learned about the Financial Independence Movement. Web searching for “best early retirement blogs” brought me to Retire by 40 and eventually to an avalanche of personal finance blogs and podcasts. Drinking from the “FIRE hose,” I became a bit of a FI junkie for a couple of years. If I’d only known everything I learned earlier in my investing career!

Where are you in your life cycle? Most people retire around the traditional age – late 50s to early 70s. Their children are grown, their partner and friends are stepping back from work, and their parents may have passed. In short, you have a lot fewer obligations at a later age. To go against the grain and retire in your 30s or 40s can be lonely and challenging. Do you think it is difficult to retire early with all these obligations?

By FI community standards, I was on the later side of “early retirement.” (I would have happily retired at 40 or earlier if circumstances had permitted.) I had kids somewhat late, so we are not empty nesters. 

Happily, both of my parents are still alive. As it turned out, my father and I retired the same year (me at 50 and him at 75). We celebrated the double retirement with a family trip to Hawaii a few weeks after I left my job.

I do think planning to retire before your kids are in college or working adds more complexity to planning. In addition to consulting with our advisors, we used the Retirement Planner in Personal Capital to run various “What If” scenarios. For example, using their “calculator” I could compare several options we were weighing in early 2018:

WHAT IF?We Retire Before Our Kids Are In High SchoolWe Retire After
High School Graduation
We Keep Our House On the PeninsulaScenario 1Scenario 2
We Sell Our House & Move Somewhere Cheaper (Geoarbitrage)Scenario 3Scenario 4

Based in part on the projected results of these scenarios in Personal Capital, we chose option 3. 

My advice is that as the variables in your plan increase, you should become more rigorous with your planning to account for uncertainty and increase confidence.

Now let’s focus on the intangibles. To be blunt, lots of people have more money than you. Most of them aren’t retired. They still work and contribute to the economy. What makes you special? How can you retire when almost everyone else in your position continues to work? Why are you different?

I certainly don’t consider myself special. Maybe just more motivated. The big factor for me was that I never felt comfortable in my skin in the corporate world. 

As both a coder and as a people manager in Software Engineering, I was organized, reliable, efficient, and conscientious — and also well respected by most of my managers, peers, and direct reports. However, programming was never my passion — and not my true calling. 

I also reached an age and point in my career where most employees would aim to climb much further up the corporate ladder. I didn’t have those ambitions and that path was going to take me further towards the parts of the profession that I didn’t enjoy. 

If you live in the United States, what’s your plan for healthcare?

Originally, our plan was to enroll in “Obamacare” to bridge the substantial number of years before we’d reach Medicare age. However, one benefit of my wife continuing to work is that we have employer-provided health insurance for everyone in our family (except our two cats). When she stops working, we’ll enroll in Covered California. To constrain the expense, we’ll try to manage our investment income so that we still qualify for subsidies.

Now that you don’t spend 8-10 hours working in a full-time job, what are you doing with your time? What’s your typical day like? Do you have a problem finding things to do?

On the one hand, I have a fair amount of routine and structure in my daily life. And on the other hand, every day is a bit different.

Since my wife still works, I take on most of the responsibility of shuttling the kids around, shopping, and running errands. The school schedule enforces an early wake-up time and a regular routine. 

I exercise virtually every day, which is one of the best upgrades of a retired lifestyle. I could squeeze in workouts only about three times a week when I was working and commuting.

Before the pandemic, my daughter and I volunteered at local animal shelters about once a week or so.

I have plenty of time most nights to catch up on movies and TV shows (a hobby that aligns with my entertainment industry interests and aspirations).

All that said, my main activity since retiring has been a return to creative hobbies and projects.

A few months after we moved, I learned WordPress and rebuilt my personal website. I also started a blog

I realize that starting a blog is a bit of a cliche for people in the FIRE community. However, my motivation was not to monetize the blog (which I haven’t tried to do), but instead to get back in the habit of writing and to get my creative juices flowing. I have posted quite a bit about personal finance, but I also write about cats, technology, and television (and sometimes mashups of those topics). However, like many new bloggers, my pace has slowed down considerably over time.

(Thinking about starting a blog? Here is Joe’s guide on How to Start A Blog.)

I also dipped my toe back into the water of audio theater production and co-founded a new troupe called Seriously Strange Audio Theater. We produced four plays before the pandemic started, including a Star Wars fan production.

While sheltering in place during the California lockdown, I started an experimental YouTube web series called “Sounds Sketchy.” We record improvised comedy sketches over Zoom. The show is a mashup of staged improv (like UCB and The Groundlings), filmed improv (like Curb Your Enthusiasm and What We Do in the Shadows), and classic sketch comedy (like Saturday Night Live). To edit and mix the show, I’ve learned the basics of video editing, which has turned out to be a lot more fun than I’d imagined.

Sounds Sketchy” recently kicked off its third season and our first two episodes feature special guest star Alan Donegan (known to many in the FIRE community for the PopUp Business School and the Rebel Entrepreneur podcast). Viewers can subscribe to the show on our YouTube Channel

I had dabbled with screenwriting (writing movie scripts) before my tech career and have picked that activity back up since retiring. I’ve written/re-written three feature screenplays and one short. So far, I’ve had luck in screenwriting competitions with one of them (which reached the 2020 ScreenCraft Sci-Fi Contest semifinals). I’m entering more contests this year with my newest script. I’ve also joined two different screenwriting meetup groups for Sacramento-area screenwriters. 

You can find my creative portfolio, and details about my various projects, on my personal website at

Am I ever bored in early retirement? Every once in a while, but not often. And not nearly as much as our two cats. 

What was your biggest challenge after early retirement?

We made a lot of changes all at once. 72 hours after my last day at work, we moved to a region of California that was new to us. In addition to setting up our new house, we had to sell our old house.

So, I had a lot of activities to manage for the first couple of months before I could relax and start to think about how to spend my time. 

Being an introvert, the biggest challenge was meeting people and building community. Over time, we met several families in our immediate neighborhood who had kids of similar ages to ours and who were like-minded politically (a relief since we are liberal Bay Area transplants living in a red area of California). 

I also started a monthly Financial Independence meetup series. Promoting it was a bit of a challenge until I moved the group into the Sacramento ChooseFI Local Group. We’ve been meeting for over two years now with a core group of regular attendees.

Lastly, when I did finally return to my creative hobbies, I started to meet people in the Sacramento creative community. 

Would you change anything about the way you retired from your job? Sometimes, I wish I stuck around for 6 more months. I could have worked out a deal and get a severance package instead of walking away with nothing.

I think I handled it about right. A severance definitely was not going to be on the menu. 

I gave my awesome manager over 3 weeks notice — enough time for her to work out a succession plan and for me to help transition my teams to a new manager. 

My last job — 2.5 years managing web, iOS, and Android development for the TripIt travel app — was a highlight of my tech career in terms of the people, company culture, and product. So, I was happy to retire on a high note. 

Did you make any big mistakes? How can we avoid them?

Beyond the basics of managing my bank accounts and sticking excess cash in CDs, I wasn’t especially financially savvy until well into my work career. So, I definitely missed out on many years of compound returns. 

With all of the educational resources available online today (especially from FI bloggers and podcasters), I’d highly recommend everyone become financially literate and financially intentional as early as possible.

How much time do you spend (per week or month) reviewing your finances, or reading about retirement finances/investment/etc., now that you’re retired?

I generally pay bills and reconcile transactions in our checking accounts incrementally as they come in rather than letting them pile up. However, I auto-pay everything I can to our credit cards to reduce busywork and earn rewards points. 

I’ve aligned our credit cards so that all of their billing closing dates happen at about the same time near the end of the month. At that time, every month, I do a full “Financial Reconciliation” where I pay off the credit cards, transfer any surplus to savings or investments, update my finance spreadsheets, check Personal Capital, etc. 

This process takes me about two hours. 

As I mentioned before, I used to consume a ton of blogs and podcasts about personal finance and FI. I still have several favorites that I read or listen to semi-regularly, but now they are just a small fraction of the total content I consume. 

What are you still not getting done/postponing, even in retirement? Perhaps some goal or something you said you’d always do when you have more time…

So far, the big disappointment has been our amount of travel. We’ve allocated a healthy travel budget into our retirement plan. However, our trips have been few and far between so far due to a range of factors. 

The biggest surprise, of course, has been the COVID-19 pandemic. We had to cancel our planned Spring Break and summer trips in 2019. And during the pandemic, we’ve been extremely conservative about traveling (taking just one overnight trip).

Even without the pandemic, we have some travel constraints due to my wife’s work and my kids’ school schedules.

Looking back on your journey, any regret?

On the financial side, I would have learned more about investing earlier. I probably missed some employer match in my 401k. And as my salary grew, I should have started to max out my 401k contribution sooner. I also didn’t learn about the tax benefits of HSA plans until it was mostly too late to leverage them as part of our investment strategy. Finally, I might have considered real estate investments. 

As for life in general, I sometimes think about one road not taken. I applied to graduate film school and got accepted into USC. Around the time I needed to decide whether to attend, I had already started working a bit in the industry (as a Production Assistant on a film shoot and as an office temp at various movie studios). I decided not to enroll since I was burned out on school (after 4.5 years at Cal). Also, I was getting some advice that making connections from industry work would be just as valuable. So, I wonder how my life might have been different, and if I would have ended up in a more fulfilling (and creative) career, had I decided to attend.

What’s your next big dream?

I’ve written an almost 40-page Star Trek parody (of the original series) that I’d like to self-produce one day as a fan film at a facility like Neutral Zone Studios (which has recreations of the original Enterprise sets). For the moment, I’ve put this dream on the back burner since it’s a daunting project — and to allow some time for the pandemic to subside.

Thank you, Randy!

That was a great interview. I love it that Randy rekindled interest in his passions. He shows that you can enjoy an interesting life after retirement. It’s pretty amazing how much he has done so far. Good luck with everything!

Ok, I need your help. I love this interview series, but I need more people to interview. The problem is this is a long post. It’s a lot of work! Please volunteer to be interviewed. I’m desperate to continue this series.

Let me know what you think of this interview series. If you have any questions you’d like to ask, leave them in the comment as well. I’ll add them to the interview. Thanks!

Previous Interviews

The following two tabs change content below.
Joe started Retire by 40 in 2010 to figure out how to retire early. After 16 years of investing and saving, he achieved financial independence and retired at 38.

Passive income is the key to early retirement. This year, Joe is investing in commercial real estate with CrowdStreet. They have many projects across the USA so check them out!

Joe also highly recommends Personal Capital for DIY investors. They have many useful tools that will help you reach financial independence.

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13 thoughts on “It Takes More Than Money To Retire Early Interview: Randy”

  1. Thanks Joe & Randy for the interview (btw Go Bears!).

    I’m also in tech and am definitely getting burned out myself. I would say for me personally though, it depends on the teams/managers I get paired up with. But at the end of the day, I don’t really want my life enjoyment to be dependent on my manager and the teams I have to work with.

    Hopefully I can reach the early-ish FIRE stage soon where I can also transition to “work optional” and double down on projects/work that I’m truly interested in.

  2. What defined your threshold to be ready to retire? What safe withdrawal rate did you assume? What are your passive income sources – dividends, etc.?

    Love that cat picture.

    I live in SF and the cost of living is brutal. While the Sierras are indeed lovely, just curious what brought you there rather than a cheaper mountain state? Doubtful l will retire in CA due to the HCOL and taxes.

    • Hi Alex – I wrote an entire blog post about how we measured our FIRE readiness. See:

      Our passive income sources will be dividends and limited (but possibly increasing) investments in real estate via a syndicate.

      As for why to stay in California, numerous reasons. I’m a native (and my wife has spent most of her adult life here). I have family in Northern California. We are weather wimps (don’t want snowy winters or humid summers). And we want to be in a firmly red state with pro-environmental policies, pro-voting rights, and humanitarian social welfare (including healthcare). But after the kids go off to college, who knows…

  3. Hi,

    Nice posts. This bring into the perspective in the importance on focusing on the present moment. What’s over cannot be undone. Forward is the way to go.


  4. I enjoyed your story very much, Randy. Thank you for sharing. It’s always amazingly inspiring to read/hear from people that retire early. One very important message I took: it’s not just about the money. Various aspects are important as well.
    All the best!

  5. Switching gears to tech is tough. I can’t imagine doing it in Silicon Valley. I came there from tech in the Boston area and found the competition with the kids out of school very difficult. However, at that time, I was more in my tech burn-out phase and more interested in personal finance and FIRE.

    I struggled with leaving Silicon Valley. We didn’t have the money to buy a house there, but I feel like there’s more opportunity for wealth. In the end, we left when our first kid was born and it seemed to work out well.

  6. Joe,
    This is an awesome piece. Good start. I really enjoyed reading this interesting story of FI journey that the length of the post is irrelevant as if reading a good book. Good pointed interview questions. Looking forward to more in this

  7. Great job on the interview Randy & Joe.

    I followed the link to your blog, Randy, and particularly enjoyed your post about becoming a vegetarian – kudos to your daughter for leading the way!. After I retired, I also transitioned to vegetarianism and, about a year ago, to a vegan diet. I think that the mindset freedom that accompanied my early retirement played a significant part in my decision to change what I eat.

    • Glad you enjoyed that post, David! My daughter and I have taken the next step and become fully vegan for all intents and purposes. My wife is almost there, but my son still enjoys eating meat when we order from a restaurant. As I mentioned in the post, I see parallels between the intentionality in the FI movement and the intentionality of plant-based food eating.

  8. Thanks for sharing your story. Do you mind sharing some numbers, such as passive income numbers or net worth when you retired?

    Loved to see the numbers, as that’s what makes things more tangible.


  9. That’s awesome that you’ve been able to get back to your creative side in early retirement. I work with a lot of engineer / tech types and you have me wondering how many of them have a secret creative side of themselves that is just waiting for the right time.

    • I think my brain is wired in an unusual way where I have both an organized and methodical side as well as a creative side. Those don’t always go hand in hand. But I do suspect that much of humanity has latent creativity waiting to be released.


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