Excelsior!

I’m originally from New York State and as such, I know the state motto: “Excelsior”. The translation of this from Latin is generally stated as “Ever upward”. I can hardly think of a better sentiment to share at the end of 2021, another challenging year for everyone. I’ve been quiet of late on this blog and I wanted to ensure I didn’t let the end of the year pass without writing at least a short post.

First, I’m doing well, and I hope you are too. As I write this, it’s now been just over 1.5 years since I left my career behind. I remain incredibly grateful and excited about all the opportunity ahead of me and for all the “possible futures” (a term I am borrowing from my Two Sides of FI show partner) that may come. Despite the challenges we all know, my family and I have made many nice memories throughout the year. Barring a few colds that have run their courses, we’ve remained healthy, and we are very thankful for this. Thanks are due to all who worked tirelessly to produce COVID vaccines, diagnostic tests, and who have endeavored in so many ways to keep us all safe and healthy.

I’ve decided not to write another milestone post until at least my two year mark. But to briefly summarize a few happenings from the last six months:

  • Our YouTube audience has grown a lot and we’ve now published 23 full-length episodes
  • We took a five-week long trip to visit family and friends we’d not seen in well over a year
  • Lorri and I started a (beer) homebrewing club in our town, and it’s coming along nicely!
  • I found a great online community in the FIRE Discord server
  • I have started to explore a new podcast + book idea (stay tuned!)

I’ve been a bit less regular about this blog of late and as I’ve mentioned before, it’s hard for me to predict what will come for it. I’m often inspired to write about what I’m thinking, and I’m happy to do so as I have good ideas. But given the energy the YouTube channel is taking – and I’m loving every minute of it! – it’s not too surprising that I don’t want to write as often or on my former weekly cadence. I remain appreciative that anyone wants to read my thoughts and I’m grateful for all the feedback I’ve received over the past 1.5 years.

Above all, I wish you the very happiest of holiday seasons, and for a healthy, productive, and rewarding year to come. I do hope that your own paths remain “ever upward” in their trajectories, and that 2022 (and beyond) brings you fulfillment of your own goals and dreams. Excelsior!

image credit: Photo by Jamie Street on Unsplash

Choosing FIRE: considering the top regrets of the dying

I came across this image in a Reddit post earlier today, after which I found this article in The Guardian. My initial response was to share the picture on social media and then with my friends on the FIRE Discord server. Why the latter? Because I was sure it would resonate with them. Contrary to one popular dismissal of the financial independence/retire early path, most don’t elect FIRE because “they hate working”. Rather, achieving FI enables a means to live life the way one chooses, including the option to stop working if and when they want. In other words, to reduce or eliminate the requirement to spend the majority of one’s waking hours working instead of doing other things of interest.

I fear that I can’t add much wisdom to the profoundly important words written above. If nothing else, I thought it would be a good opportunity for me to reflect on how my FIRE journey is very much related to several points contained within. Above all, I hope in sharing this that it might cause you to consider whether you are making the best choices you can to honor your inner needs and desires, avoiding later regrets. To repurpose something I usually say in another context, the best time to start doing so is yesterday, and the second best time is today.

I wish I’d had the courage to live a life true to myself, not the life others expected of me

I’ve never felt pressure from family to achieve X, nor was I told that only path Y was the “right one” for me. I know this isn’t the case for everyone, and I’m truly thankful that I’ve not experienced this. As such, I’ve felt comfortable living the life I wanted to live as an adult. But I have certainly had my choices challenged by former colleagues or friends at times, particularly when it came to job changes. Most often they had good intentions and believed they were supplying me good career advice. But I was on a different path and the difficulty was that I didn’t feel comfortable explaining that until the very end of my career. Quite honestly, I wasn’t very courageous about describing my path and the rationale for it, and that created challenges.

I didn’t always know about FIRE but I did know early in my career that I wanted to retire early. I also didn’t know how I’d achieve that early on. I didn’t magically come to my career “leveling up” strategy. Rather, it evolved through several early moves in my career and seeing the benefit of the same. I realized that by building breadth in skills, and not fearing moves into new companies and stretching beyond my comfort zone, that I could accelerate my path. Importantly, my wife always supported me in this despite the challenges it meant for our family. We believed in the end goal we were seeking. While my path was not the traditional one, I’m not sure that it was courageous. But I can say that I’ve tried to honor what I knew in my heart I wanted to do. And here I am!

I wish I hadn’t worked so hard.

I really like this point and yet I’m of two minds on it. First, the obvious one: By achieving FI at age 46, I eliminated the requirement to work until traditional retirement age. I therefore created the option to stop working so hard, and I took advantage of that just over a year later when I left the workplace. So conceivably, I have been largely successful in avoiding having this regret. Right? Mostly.

In my case, electing this path meant a series of tradeoffs were made along the way. Part of my journey included several roles at start up companies, meaning very long hours spent at work and therefore away from home. It also meant frequent jobs changes and associated moves away from family and friends. In the second half of my career, the roles I had involved extensive travel, which meant more time away from my wife and daughter. All of these had impact on my family and meant that I wasn’t always there for specific events, or at times in my daughter’s early years, just to name a few. Were those the “right” decisions? My wife and I accepted them with eyes open and as a team. But they had a cost.

To be clear, I’m not complaining. Yes, I worked hard. But many people work just as long or longer hours, do harder/manual labor, do it for many more years than I did, and are compensated far less for their efforts. On net, I believe the choices I made were the best for my family and so I do not regret them. But it’s worth reflecting on what it took to get here and be doubly appreciative for what I have now. I am very thankful that I no longer need to work so hard.

I wish I’d had the courage to express my feelings.

Me being me, this one warrants a whole post unto itself. But I’ll be brief in the moment. Suffice it to say, I don’t usually shy away from my feelings. One of my favorite things about my FIRE journey is that I now feel the freedom to share more openly about it. Don’t be mistaken – I still hold back at times, as my Two Sides of FI show partner is correct in reminding me. But through this blog and our YouTube channel, I’ve become more comfortable with openly sharing my feelings (to an increasingly larger audience!). That’s been really good for me and I hope that it helps others as well. At times, I admit that all my corporate training still wins out, and I choose my words more carefully than I should, muting the emotions underlying the point I’m making. But i’m improving and I feel strongly that having the freedom that FIRE has provided is helping – in all things, not just in content creation. And I’m really happy about that.

I wish I had stayed in touch with my friends.

Generally speaking, I think I’ve done a good job with avoiding this regret. I’m a pretty nostalgic person and enjoying keeping in touch with friends made through the years. That said, leaving the workplace and my prior and subsequent moves have created physical distance between me and my friends. True, I now have the time to travel more frequently to see them. Since leaving the workplace, I have taken several opportunities to visit out of state friends, which wouldn’t have happened were I still working. And this has been hugely positive for me. Not having a work calendar and a vacation days allotment is so freeing.

On the other hand, as we’ve discussed on the YouTube channel, FIRE does have a way of creating distractions if not challenges to friendships. Not everyone sees the validity in this path and may have difficulty talking about it. Honestly, it’s hard when you don’t feel comfortable discussing something so important to you with close friends because of how they react to it. I’ve certainly not worked through this yet but it is something I think about a lot. I do need to write more about this, if nothing else. I’ve got more to process here, and it’s important. This is one area in which FIRE path folks need to be prepared. I want to remain close to my friends irrespective of my path, assuming they’re willing.

I wish that I had let myself be happier.

We can’t control everything in life. Misfortunes and hardships may come at any time. That said, it is often spoken that we choose how we react to these things. I will freely admit I did not always choose happiness. While working, I often let many things get to me, compete for my time, and challenge my wellbeing. Like many, the ever-present cellphone became a real difficulty for me. The text messages and emails from customers and colleagues were never ending, and I found these impossible to ignore. This certainly affected my mood at times as my family will attest. Naturally I could have done more to deal with this, and I’m surely not saying FIRE is the only solution! But electing to follow this path has been an important part of me deliberately choosing happiness over stress.

The important point to make here is that I am very happy and I am increasingly choosing to be so via this path. I know how fortunate I am to have achieved what I have, and I remind myself of that often. I am truly grateful that my wife and I get to choose our path forward from here. Are our options limitless? No. We don’t have a Fort Knox-like stash of gold to fund an insanely lavish lifestyle. But we do have the freedom to live well without the requirement to work – and that’s huge! We are in good health, are relatively young, and have many options available to us. It is now on us to create the life we wish to live from here on out, for the remaining years we are vertical on this planet. It is overwhelming in some respects but we absolutely look forward to the challenge of determining what to do to maintain and grow our happiness in our life together!


Will I have regrets as my life nears its end? I have no idea. Like most people, there are things that I wish had happened differently; that I had made better choices or avoided hurting others by my actions or via neglect. I am far from perfect and I can’t change that. I do know one thing: I think it highly unlikely that I’ll regret my decision to follow a FIRE path. I wish you life devoid of regrets and full of happiness. Mahalo. ?

image credit: Photo by Brett Jordan on Unsplash

The profoundly important value of finding community

By nature, we humans are drawn to tribalism and community – that is, we like to gather in groups around shared interests. I’m not even an amateur sociologist so I’ll leave it at that. But I doubt anyone reading this will disagree with my statement. Some associations are incredibly close, such as those with our families, partners, and our closest friends. Others are rather casual and fun – fans supporting the same sports team and enjoying each other’s company, even if only briefly at a bar or a stadium. Most of the groups in which we find ourselves are somewhere on the spectrum between those two extremes.

When it comes to financial independence, retire early (FIRE), it can be difficult to find people with whom you can talk with full disclosure. The ideals of this path are rather foreign to some, and often merely suggesting your interest in FIRE to somebody can be met with confusion, derision, or even complete disgust. My YouTube show partner, Eric, and I have talked about this in several episodes on our channel (here, here, and here). Of course your spouse or partner is an active participant in the journey so they are a valued confidant. And perhaps you’re lucky enough to have a good friend on the journey like I do – these days, but I didn’t earlier on. But many people don’t have any of these. Where to turn?

The internet can be a positive place for discourse…right?

As one who’s been online since the early days of what we now collectively term as the internet, I’m the last person to claim that it’s a wondrous land of only positive interactions. But it’s also difficult to argue with the fact that there are topical communities of all kinds, across a breadth of platforms, where one can find like-minded folks. Groups of people with similar interests congregate in forums, in groups on Reddit or Facebook, on chat rooms + servers, in the comments sections of blogs and YouTube videos, and the list goes on. There’s certainly no shortage of options. But what is actually useful?

I think all of the above have their place. FIRE-themed blogs and YouTube channels tend to be very high quality content, since many creators not only have first-hand experience, but also generally take the time to research and perhaps even reference their content. So even from a purely informational source, there’s plenty of value. I would assert that similarly themed forums and groups are also pretty useful, while being less formal in nature. But the bar to content creation is much lower in these platforms, so you get the benefit of a diversity of experiences and a much higher volume of materials to take in. This can also lead to signal to noise issues, of course.

All of the above forms of content creation generally have a social aspect to them as well, in the form of comment sections and otherwise providing an ability to reply and engage with others using the resources in question. The quality of experience here differs by the specific group or forum, as well as based on what the topic is. Trolls can of course raise their heads anywhere, though there is often moderation in place to manage this. There’s also the challenge of those lesser informed or simply who have an axe to grind to disrupt otherwise productive discourse. There are good reasons why some people say “never read the comments” – though of course doing so means potentially missing out on really valuable – and personal exchange.

Enter Discord, and the benefits of live community engagement

I extensively used (and still do to a lesser degree) all of the above resources on my path to FIRE. In fact, I discovered that FIRE “was a thing” via the very same, after years of saving towards early retirement before realizing others had similar goals and a framework to get there! But once I achieved financial independence and left my career at 47, I found I was craving something more. When I posted on those forums I sometimes received appreciative responses from those earlier on their journeys, but it wasn’t very engaging. The experience was often rather one-way. But one day I stumbled across a Reddit post about a Discord server dedicated to FIRE (What is Discord? for more info). I’d used this chat service in an app coding class before, and my teen sure used it a lot to talk with her friends. But how would it be useful to me now? I was certainly intrigued!

It turns out it’s been really great for me in several ways. First and foremost, this community is filled with a diverse group of several hundred people, all of whom have one very important thing in common: they’re all on a FIRE journey. Some are still in the early exploratory stages, while a few are out the other side, post-RE. Most are very actively working towards achieving FI. That makes it a really safe space to talk openly about a topic that can be challenging to discuss with others not on the path. Some of these people haven’t yet shared their aspirations with close friends or families, yet here they can talk openly – and completely anonymously if that’s their preference. Importantly, it’s also an incredibly supportive and largely very thoughtful group of people.

I particularly appreciate that there’s a broad range of ages represented among participants, as well as a diversity of geographic locations. Admittedly, there aren’t too many 40-somethings on the server – yet (Discord being much more popular with younger people) but I was happy to see another “old guy” online yesterday. There’s also a much broader gender diversity than I typically find among the other resources I listed above. Not to put too fine a point on it, but nearly all of the most popular FIRE-themed blogs and YouTube channels are led by men, and those are largely white Americans in their late 30s to mid-40s. That’s definitely not the case on this server, which is hugely beneficial in my opinion. I learn so much by engaging with a more diverse group of people (hint: diversity and inclusion has real value).

Where I find value in participating

One thing I truly appreciate is the open exchange on the server. Because the platform allows one to be as anonymous as they like, information is shared with a huge degree of freedom. Many on this server share their full financial pictures, their goals, as well as their successes and challenges along the way. This is so valuable for others on the path who may have had no good reference points prior to joining the server. I sure wish I had so much data available, along with an ability to ask questions in real time when I was much earlier in my own journey! It’s impossible to overstate the value of that in providing education and actionable information to help you develop and refine your own FIRE plans.

Due to the channel infrastructure used on Discord (configurable by server) it’s also super easy to focus on (or ignore) topics that are (or not) of interest to you. Cryptocurrency not your thing? Mute that channel or don’t spend time there. Want to ask questions about your portfolio? Head on over to #investing and see what people think about your asset allocation. There are also wholly social channels to talk about hobbies, cooking, or travel – just to name a few. It’s pretty handy to have a “one stop shop” all under one roof and some use it more socially than others – it’s a personal preference. You can also DM with people.

I’d be remiss if I didn’t point out the incredibly valuable feedback I’ve gotten from our server’s community on my own content creation. I know that whenever I share an article or a new video, I’m going to hear from at least a few of the folks I interact with most often. And their input is so helpful to me – and I probably don’t thank them enough (thank you!). True, comments on the blog and on YouTube come with increasing regularity, and those are also useful (thank you, too!). But there’s just something different about getting input from people you know a bit better – and understand their viewpoints more. I’m honestly so thankful for their willingness to help me improve my content.

Go find your people!

I believe we all need to find community, and also that it can take a variety of forms. For those on the FIRE path or who are interested in learning more about it, you have many options at your disposal. Personally, I still consume content from all of the different sources listed in this post. Of late, I’m certainly finding some of the most value in this FIRE Discord server. If it sounds like something you’d like to check out, this link is your personal invite! It’s a free service and (sadly) I get no kickbacks for referring you. I’m just happy to share a great resource! If you do stop by, please be sure to say hi to me when I’m on:

PS – I’ll take this post as a reminder that I really need to make a good Resources page for this blog so I can share all my favorite blogs, subreddits, etc. with you!

image source: Photo by Hannah Busing on Unsplash