Financial independence and the freedom to choose…to work?

More than a year ago, I wrote an article titled “When can I retire?” That piece was largely about achieving financial independence (FI) – that is, when your assets can securely cover your anticipated expenses for the duration of your lifespan without reliance on your current employment income. That said, achieving FI does not mean you have to retire early (RE). It simply means you have the freedom to do so when you are ready. In other words, you have the option to retire. But that freedom gained from FI enables other options as well!

For the last few days I was visiting a college friend. We had a really great time doing all sorts of things, including going wine tasting as pictured here. Hanging out without other people around most of the time (weekday travel is the best, and a real benefit of me no longer keeping a “standard work schedule”) meant we got a lot of time to catch up and chat. Flying home earlier today, I realized his story was a worthwhile jumping off point for an article!

The freedom to pursue a new venture

Until about five years ago, my friend had a very successful career at a fast growing company. He was a business leader at a technology firm that was later acquired by a much larger company. At that point, given his many successes on that career journey, he could have stopped working entirely, just as many choose to do once they achieve financial independence. But he didn’t! In fact, he moved into another career entirely – in a totally different business and segment, at a company he’d helped to found five years prior.

Fast-forwarding to today, my friend is now the CEO of that company, one presently in its ninth year of operation. The business is growing well and he is still working full time. Wait, what? You read that right – and there’s absolutely nothing wrong with his decision! The freedom to spend your time how you wish might including taking the opportunity to be an entrepreneur, to follow your passion, and grow a business. Yes, that may include taking on another job after you leave your primary career. Many people choose this path and find it incredibly rewarding. Sounds great to me!

Is he happy? By all measures I have at my disposal, absolutely. My friend is at a great company, enjoying making products he believes in, working with a strong team of talented people. He and his family are living where they want, and he is no longer traveling the crazy hours + frequency at which he did when he was in his former career. Talking with him, it’s clear that sometimes he misses the positive parts of business travel – as well as aspects of his former career. I can certainly identify with all of that. I loved much about my career! But it’s also clear that he is super happy to be around his family a lot more, helping to raise his kids. I can identify with that too! But wait – wouldn’t he earn more money if he stayed in his former field? 100% yes. And I could say the same thing. But we don’t need to, and we both elected to walk away from our highest earning years to take a different path.

“Yes, there are (at least) two paths you can go by…”

Led Zeppelin certainly wasn’t writing about the then not-yet-named FIRE movement in “Stairway to Heaven”. But that lyric is an apt way to frame the point I want to make: to continue working or not is just one of the high level choices to be made once you achieve FI. The first option can itself take many forms: many continue to work in their existing job for some time, post-FI. It may be because they love the work, or want to keep at it for some period of time. I worked a year longer after hitting my own number. There were several reasons for that, including wanting to finish working on a project of which I was a team member. Other people might elect to stay in their job but reduce their hours or number of days working. Still others may choose to work in a new field entirely, or like my friend, start their own company!

As regular readers will know, I haven’t yet elected to start working in a new career, and I don’t think doing something full time is likely anytime soon – barring perhaps at a business I start myself. Outside of the one day a week I pour wine at a local tasting room, I don’t have “a job” right now. Rather, I have spent most of the first fifteen months since leaving my career exploring different areas of interest to me, learning new skills – like content creation via this blog and the Two Sides of FI YouTube channel, volunteering, and essentially “random walk”ing through a wealth of different things. I’ve also written about and filmed a YouTube episode about all the things I have learned so far after more than a year since I left my career. See those links for more details.

Any of these choices are “correct” so long as they resonate with you and are aligned with your earnest interests. I fully agree with something that my friend told me a few years ago when we discussed my plans to retire early: “People need to feel that they are contributing to something that they are passionate about. Make sure you know what that is.” He’s right! My passions don’t presently include working for someone else, and certainly not in my previous field, but perhaps that will change should the right role with great people comes up! Or if my wife and I elect to start a small business in an area we are passionate about (yes, yes, I know some of you really want me to start a brewery!). Who knows? In the moment, what feels right is exactly what I’m doing: exploring!

What are your plans? If you’re not on the FIRE path but you suddenly won a $10M lottery prize, would you stay in your job or would you do something else? I’d love to hear from you!

The many learnings from year one of early “retirement”

ONE YEAR since I left my job? Wow. Particularly given the odd pace of “pandemic time”, I find it hard to believe I’m already at this point. But here I am! Looking back at the countdown calendar that formerly hung on my office wall confirms it. On an afternoon exactly one year ago today, I handed in my employee badge and drove out of the company parking lot, almost certainly bringing my 23-year biotech career to an end. A few weeks later my family moved out of the Bay Area to the Central Coast of California. I wrote my first blog post here several weeks later. Now after twelve months and 43 posts, it’s time for another in my series of milestone articles. Will it be my last? Who knows!

After a year I still generally avoid the term “retirement” or I place it in quotes as I’ve done here. At 47 years old, I still think it unlikely that I’m completely done with all things that could be termed “work”. It is true that I leveraged reaching financial independence to step away from the only career I’ve had – and still have no intentions of going back. But it’s also entirely possible that one of the many ideas I’m exploring could turn into gainful revenue generation. Again, who knows? That flexibility is exactly what I was targeting with my FIRE journey. That said, I can’t imagine myself schedule-bound to an office job at someone else’s company. ? It seems more likely with each day that this will continue to be the case.

I have approached this article differently than my earlier milestone posts. Instead of my usual (rambling) long-form, I will briefly summarize some of they key lessons I have learned and observations I’ve made. That seemed a better method to share a broad range of information without a really long article. I’m hopeful that this bite-sized approach will work out well and perhaps will provoke questions that would be fun to expand upon! So without further ado and in no particular order…


  • It can be very difficult to resist the temptation to fill all your time with “stuff”. Our careers train us in this way and it takes active effort to get comfortable with anything else. But I think that having truly “free time” is vital to allow the creative process to happen!
  • Like any big changes, leaving your career behind is an emotional roller coaster with many highs and lows. You can’t truly prepare for that, short of just being cognizant that the mental churn will happen and is completely normal. It’s really important to reflect on what you’re feeling. Journaling or blogging can help!
  • Talking openly with your partner & family is really important. Sharing the emotions you’re feeling helps everyone. After all, they are going through this huge change with you! Keeping it in will only create tension that helps nothing. Ask them how things are going now that you’re around so much more and see if anything needs to be adjusted.
  • If your identity is tightly wrapped up in your former job as is common, it will be a substantial change when this is removed. Thinking about your purpose and what defines you and is important now, is really useful. What is your next phase of life going to be about?
  • Don’t fear trying things and setting them down. This is the very heart of having the freedom to choose how to spend your time. If like me you have many interests, it’s perfectly OK to try them out only to decide “that’s enough for now” or “I don’t actually want to do this”.
  • Related to the above – it’s important not to pressure yourself to find “the next thing to do”. At least in my case, this created stress in the first few months. Financial independence means that additional income – while nice, is not required. Your time is better spent exploring, from which may spring that next great idea! But don’t rush into anything hastily.
  • It can be really tricky talking about FIRE and early retirement – particularly with people you’re meeting for the first time. I often refer to my increasingly rare consulting gigs as my “job”. Yes, it’s a cop-out, but it works before I get to know someone well. It’s worth thinking through how you will handle this in advance. You’ll get lots of practice, I promise you.
  • The things you miss about the workplace may surprise you. Giving some thought to this before you depart may help you identify other ways to satisfy those needs – but it won’t be perfect. Again, this is just part of the emotional roller coaster that will surely come.
  • Many workplace friendships are just that, and they won’t all persist after your shared work life is no longer there. COVID + moving certainly didn’t help in my case as visiting people wasn’t an option and Zoom meet-ups are only so effective. But I am convinced that many relationships at work are very much tied to the workplace itself. This is perfectly OK!
  • On a related point, it’s easy to under-appreciate how much socialization occurs at work. What will you do during those weekday “working hours” while your friends are busy? Finding appropriate avenues to engage with others is still really important. Clubs, civic groups, volunteering, and other means to find like-minded people is important – particularly if you relocate in retirement, as I did. Pouring wine at a tasting room one day a week is proving to be fun for me and plenty social!
  • Lots of people make bucket lists of big and small things they intend to do once they retire. I have found since leaving the workplace that I continue to generate ideas of things I might like to do. I keep these out of sight in an “idea funnel” that I revisit from time to time. It’s fun to see how my thoughts change about prioritization; there’s also no pressure to feel like it is a “to do list” that I must achieve. This subtle difference feels really good to me.
  • Building skills and “making” things are really effective ways of continuing to challenge yourself, to keep learning, and also to feel productive. They are also great mechanisms to unearth potential business opportunities or at least new hobbies and avenues of personal entertainment. Knocking procrastinated chores off your to-do list only lasts so long!
  • Just because someone is willing to pay (a lot) for your expertise doesn’t mean it’s the right thing to take on. I’m grateful to have been presented many consulting opportunities over the last year. While tempting, I’ve had to be really careful about not over-committing at the peril of being unable to do all the other things I want to do! Be sure to choose wisely.
  • The freedom gained via FIRE has proven to be well worth it! I love being able to choose how to spend my time. I can’t count how many times I’ve woken up with zero plans and at the end of the day realized what a fun day I had, just taking things as they come. My wife is much more spontaneous than me and I’m finally starting to understand the joy in this.
  • On a similar point, I’m really excited to finally get the chance to test out our interest in longer term travel. This summer we’ll take a five-week trip to visit family and friends. Wow! Like most Americans, we’ve never been away more than two weeks on vacation. It’s a little scary, but almost entirely in a good way!
  • There is no “right way” to do this. From talking to others, whether in FIRE or traditional age, retirement is definitely individual. We each have our goals, our interests, and our individual preferences. I think many of the points herein apply broadly. But you will each need to determine what is important to you and how you will spend this next phase of your life.

I hope you’ve found this post useful. I remain incredibly grateful to be in the position I am, something I reflect upon often. It is my earnest hope that in sharing my experiences I can assist others in their own journeys. Decisions relating to retirement are among the biggest we make in our adult lives. There are many paths to arrive at that goal and so many decisions to be taken along the way. And yet as has been well documented, few people feel well informed on the topic by the time they are deciding when and how to retire – or worse when others have decided that timing for them. I aspire to change that however I can.

Above all, I wish you all the best in your own journeys! If there are any questions that this post has prompted or areas in which you’d like me to dig in further, please comment below or on social media. I’ve learned much from the interactions I’ve had with readers and some of my favorite posts have comes from conversations with you. I just want more of them!

If you’re not yet following my Two Sides of FI YouTube channel (or the audio podcast version: Apple, Spotify, or search your provider of choice!), please consider it! My co-host, Eric, does a really great job of challenging me and asks thought-provoking, and sometimes difficult questions that I’m not always willing to put to myself. And I think you’ll find his perspective as one approaching FI incredibly valuable. Mahalo! ?

Invest early and often to ensure your financial goals are met!

Last week we posted “Don’t Make These Financial Mistakes on the Path to FIRE!“, our longest Two Sides of FI video to date. We had so much to say on the topic that even with splitting our edited footage into two parts (part 2 is now live as well!), it was still long. Why? It’s simple: none of us come into this world as personal finance wizards. We stumble through life making financial mistakes in assorted ways. Most of us make lots of them! That definitely turned out to be the case for us, and we enjoyed discussing our many misses along the way. I encourage you to check out the video!

The episode originally had much less of a clickbait-style title. But when we saw the early traffic wasn’t at our usual level, we amped up our marketing! As I suspect we all know well, humans are rather emotional creatures. Many people worry a lot about money, often for very good reasons. But even the more fortunate among us are no less emotional about cash. So our sensationalist headline did result in an uptick in views! Thinking about our conversation in this episode prompted me to write about a common issue that we discussed: wishing we’d saved more, earlier. Read on and avoid our mistakes…

Most of us get a slow start when it comes to saving and investing

Few of us had the knowledge and/or initiative to become big savers growing up – even if we had jobs throughout our teens, as Eric and I both did. As soon as we start earning money, we generally spend it. Sure, plenty of us start savings accounts – we did too. But humans aren’t born with a desire to save and invest. Generally, someone has to introduce us to the concept and convince us of its merit. Unless you’re from a wealthy family, that often doesn’t occur until your first “real job” after high school or college – and only if you’re fortunate enough to work somewhere with a retirement savings plan like a 401(k) or a 403(b).

Even if we do take advantage of those workplace plans, many of us fail to realize the merits of participating fully. How many among us have contributed to a retirement savings plan but didn’t save enough to achieve the full employer match? That’s equivalent to saying “no thanks!” to free money. Yes, I know it can be hard in those early years. As I whined about often early in my career, I was the lowest paid of all my college friends in my first job out of school. It can feel like a real struggle to meet all your obligations and save enough. But even if not right out of the gate, as soon as you can, it’s important to kick up the savings. It will yield huge leverage over time as I’ll share below. Not doing that soon enough is a common financial mistake – one often not realized for many years. A sobering fact: according to Vanguard, in 2020 the median 401(k) balance at age 65 was only $65K. That means half have saved less than that.

The best time to start is yesterday and the second best time is today

So you got a slow start – or haven’t invested at all. Is it too late now? As some will know, one of my favorite podcasts is The Money Guy Show. I’ve been listening to it (now I watch on YouTube) for 8 or 9 years. The title of this section is something I’ve heard hosts Bo and Brian say many times over the years. Sure, it’s best to start saving early (and often), but is it ever too late? Technically, no – but playing catch up becomes harder and harder over time. One of my favorites of the great free resources they have on their website is the Wealth Multiplier. It describes how much money you need to save and invest monthly to reach $1M by age 65. How big of a difference can a few years of savings make? Check out this snippet from their chart:

My favorite take-home from this picture is one they point out often: you have an 88X multiplier on your savings when you start at age 20. In other words, every dollar you invest at 20 can yield $88 by age 65. By comparison, at age 25 that multiplier is down to 44X, at 35 it is less than 13X, and just over 7X by age 40. Download the full table and you’ll see that it only gets worse from there. Translating that into monthly savings, you’ll agree there’s a huge difference between saving $95 vs. $780 each month comparing ages 20 and 40. Wow, right? Particularly for those who don’t love math, I think this image best shows the power of compound interest over time as compared to a graph.

Putting it in context

Eric and I both saved early on and took part in 401(k) plans and other savings vehicles over time. But neither of us would say we took full advantage of those plans in our earliest work years when the multiplier was huge. As we discussed, we did have some financial missteps, challenges, and setbacks along the way – I got divorced, we had student loans, my expenses went up due to relocation, we started families, etc. But even so, in hindsight we know we could have saved more, sooner. We didn’t prioritize saving as early as we could have. Neither of us fully investigated the investment options available to us in those early years. We are both fortunate to have gotten much smarter about things eventually, and benefitted from our career successes which enabled financial catch up. But things could have gone very differently if we hadn’t.

I won’t go into all the details here, but there are many other aspects to consider on this topic, some of which we touched upon in the episode. There are a variety of different tools available for investing depending on the country in which you live; each of which has their tax benefits and other aspects to consider. In the US, these include Roth IRAs and Health Savings Accounts (HSA), just to name two. Particularly if you are early in your career or maybe even still in college, I encourage you to investigate these options. Roth IRAs in particular are a very powerful tool and are available to you as soon as you have earned income. Wisely, Eric has already gotten his working age kids into Roth plans!

But isn’t it difficult? I don’t know where to start!

Above all, don’t panic! This does not have to be complicated! If you have a workplace savings plan and are wondering how to get started, look into target-date mutual funds. These are simple and effective plans that run on autopilot. They have very low fees and auto-balance your portfolio between stocks and bonds relative to your age and time to retirement. And if a plan isn’t offered through work? Have a look at some of the Books listed on our Two Sides of FI website. In particular, I’d recommend The Simple Path to Wealth by JL Collins. This fast and easily digestible read is chock-full of investment guidance that you will understand immediately and can readily apply. It’s very popular for a good reason.

Now get out there and save! I wish you all the best in your financial journeys!

image credit: Photo by Tech Daily on Unsplash