
This time of year is typically when the winter blues start to hit me.
I’ve got too much to be grateful for to complain, but the slog of winter doesn’t bring me a ton of joy. Some incredibly real and awful events happened to a friend of mine this past week.
Time to show some strength for him and his family. The struggle of life smacks us right upside the head, and often when we least expect it.
In this post I’ll share what it’s like to be stuck at the retirement crossroads, and the struggle to regain focus on what truly matters.
Retire or Not Retire? The Retirement Crossroads Are Here
There continue to be layoffs and major reorgs going on at work. I don’t know most days how “secure” I am in my position.
That’s pretty ironic after I’ve written about surviving the cubicle jungle. Sometimes it just doesn’t matter how savvy you think you are.
We can only control so much.
The thing is, I’m not down about that. I’ll always maintain that the most important aspects of the FIRE journey are two-fold: One is getting your financial house in order. Be prepared in case your job is suddenly at risk or some emergency pops up. The second important aspect is mastering mindfulness. Know where your true priorities lie, to avoid regrets later on. Simple stuff, right?
75 Days Until I Do What Again?
Decisions, decisions! Not that I’m driving my wife nuts with my early retirement indecisiveness of late, but I’m at the proverbial crossroads now. Like an Upper Midwest winter, I grow less tolerant of workplace baloney even as I get better at learning how to manage it. New boss, new direction, and more “storming and norming”.
But again I’m fortunate. I haven’t been given notice (yet) of my job being eliminated.
It’s quite tempting to want to call it a day come mid-March and put cubicle life behind me. Except … I feel like I’d be running from a challenge and ignoring growth opportunities. Set aside a few of the bad eggs at work and generally, our office spaces surround us with the same mix of people we’re friends and neighbors.
Some jobs call on us to improve how we interact with others while we improve the bottom line. Yeah, most of it is total bull$h*t, but there’s a sliver of value to that dynamic. Good thing, not all workplaces are the same. We can hop from one cubicle lily pad to another, and another, until we’ve found (or created) the Team (capital T) that works for us.
If I just up and leave, what will I do next? I could see myself enjoying a two-month sabbatical. I’d focus on writing new blog posts and catching up on some rental maintenance work. Eventually, I’d start to miss being surrounded by a bunch of people I barely know, don’t know at all, or know too well and can’t stand (i.e., the office).
Early Retirement Irons in the FIRE
Being the consummate overthinking, overanalyzing planner, I’m probing each fork in the road. There could be another job in an entirely new setting around the corner. Odds are I might just stay put but find a different department with familiar faces, assuming they’d take me.
Thing is, I don’t think I can stomach walking away just yet. Not for fear of lost social interactions. Not for fear of lost pay and benefits. But for fear of lost pride.
Maybe this is the lesson: wait too long to retire early and you start to take work personally. You’ve become conditioned to that life behind bars. It’s as if everyone around you is working towards that same Boy Scout badge, and you’ve got to get yours too. FOMO from cubicle life??? To retire or not retire becomes an understandable condition.
I give a lot of credit to all I’ve read about who have retired early and managed to avoid cold feet or regret. Granted, the big shots in our FIRE landscape have created meaningful substitutes for co-workers through creating a FIRE community. They’ve replaced cubicle work with projects that keep their minds engaged and lives enriched.
And that lesson my friends is obvious: there is no giving up work or value creation and social bonding when you retire early. Not if you give a crap.
Now, I am a bit envious of the early retirees who’ve hung it up and managed to avoid taking up new projects or establishing new social networks. They’re the naturally introverted set and gravitate to solitude, they’ve found their path and it works amazingly well for them.
I thought I was among the introverted crowd for a good chunk of my adolescence. But when you find yourself alone as I did one summer during college and you start to malfunction due to a lack of people around you, you realize right quick how important people are. Even the borderline annoying ones.
(So give your more annoying cube mates some knuckles today in appreciation for their simply being there, fighting the iffy fight with you!)
Side Hustle Adventures
The break-in at Rental A created a whirlwind of work for yours truly. I’ll come clean here and now and remind you that being a landlord is not always a passive exercise. Sure, you can go months on end without a peep, but when an emergency like a burglary happens, you need to be ready.
The frugal mister that I am, I opted to replace an entire entry door, in the frame, by myself. It took some patience and bravery, having never done this before. But thanks to YouTube, and a contractor who was willing to walk me through a few steps over the phone, gratis, I got the job done.
See, we’re all capable of more than what we realize. Circumstances sometimes force us to find that out about ourselves. Other times we boldly take the initiative. In this case, I put in a couple of days of work (one for popping in the door, another for getting the trim back up) and avoided spending over $2,000 for someone else to do the job for me.

I’m also hyped up these days about going even more vegan than before. Having watched The Game Changers on Netflix, I’ve got a new appreciation for why plant-based diets are incredibly superior. I won’t give up the occasional filet mignon. I’m not fully turned to the Dark Side just yet…
Mrs. Cubert and I also screened That Sugar Film on Amazon PRIME recently and wow – another huge eye-opener about the damage sugar can do (no, all calories are NOT equal!) The scary part is how that crap, in all its forms, is hidden in just about every processed food on the shelf. If you’re a Mountain Dew drinker, my heart goes out to your dentist…
Still learning how to live my best life, while shuffling about at the crossroads of my corporate journey. Life is beautiful!
Join the Legion of Cubicle Doom!
Sign up to have new posts and special updates sent directly to your inbox.
You can do it! I had my own set of cold feet, driven by life uncertainty and some big financial rewards for making it eight extra months.
Personally those last eight months came at a big cost and I’m unsure if it was worth it. Burnout is real. I was good at my job, sometimes passionate about my job, and enjoyed the people I worked around, but it was still a means to and end. Now that I’m six plus months out from leaving, I realize that work came at the expense of everything else. Family, hobbies, friends, travel. I’ve had fleeting moments about going back, but those quickly vanish when I think about a loss of the freedom I have today.
Pulling the plug is hard. Its giving up something you’ve known for half of your life and almost your own adult life. I understand.
Maybe you can manuver a layoff and let them make the decision for you. Best of luck
Hey Robert! Thanks for stopping by and for sharing your words of encouragement. This is a good shot in the arm for me. Curious, how have you been able to replace the day to day relationships and social cohorts in your post-cubicle life?
a layoff doesn’t sound like the worst thing in your situation, cubert, but i’m not in your shoes. i know my large company generally offers a nice severance package to longer tenured pawns.
my cross country coach in college gave us a summer reading list back in the late 80’s. it included a book called “sugar blues” which was probably ahead of its time. sounds about like a similar concept to your movie. good luck with your decision.
That’s a great point, Freddy. I’m going to swallow my pride if something happens. More likely, I’ll find a new path and drag out this thing. Regardless, I’m going to make the best of the journey and consider this “dilemma” a true blessing. Most don’t get to fret over these kind of options!
Super honest post—as usual., good stuff. as a guy in his mid 50’s with a C-level job I understand the difficulty in walking away. In this society, so much of how we think about ourselves is predicated on what we do.. I’ve been trying to separate what I do from the idea of who I am—not easy. I gave notice (not public yet) to the powers that be in our Corp that I’m leaving.. and was enticed to stay for an extra 5 months by a six figure retention bonus—two months in it feels like I should have just walked..
Thank you, Sir!
I appreciate your honesty about the cost of lingering on longer than you wanted to. The dollars are nice, but the time is something you can never get back.
In my company I refer to myself as a free agent with a 1 year contract. We have layoffs every July so when you make it through that, you feel as though you’re good for another year. I only have 6 more of those to go through before my own timetable to leave hits.
Hey Rex – Wow. That’s no way to live, man. Every single year, to have to go through that gauntlet? Reductions in force definitely happen and happen often at large companies, but you can’t retain talent if you’ve always got teams on edge. I wonder what the prospects are like for your company based on this approach?
Sounds like our workplaces are pretty similar, Cubert. The amount of layoffs and the pace of change is truly ridiculous at my office right now. Hard to see the wisdom in a lot of these decisions.
We’re very close to pulling the trigger but think we have at least one more year in us, if only to pad the accounts, save up a college fund for 2nd, yet-to-be-created baby, and enjoy that paid parental leave, if nothing else. But sometime early next year…
That said, I, like you, contemplate both options. My wife likes her new job and we both may stay on because as much as I don’t love the job some days, it’s by far the best one I’ve had and overall, is particularly good for a j-o-b. The should I stay or should I go now syndrome is strong.
Hey, my brother! Indeed, eerily similar… I hope you’re keeping your head down through your situation. That sounds nerve-wracking as all get-out to me.
One more year isn’t bad at all. Especially if it’s in your 40s or even early 50s. So many will struggle to walk away in their 60s the way we spend and the way our society values health care and safety nets…
I’m with you all the way — very few FIRE peeps come back to the cubicle, but for some reason, those of us near the goal line struggle with this bizarre cold-feet syndrome.
I worked longer than I needed to because they were throwing money at me and it felt great to be getting 150% more income than I had been used to. But I did leave and haven’t missed it a single day. My limited consulting and my significant volunteer jobs keep me busy enough. Since I left I’ve turned down an additional 300% increase over my best year to go back, when I said no to what used to be six years of compensation for a single year’s work I knew I was at peace with retiring.
Hi Steve! Your story is pretty unique. Tough to walk away when they keep clasping those golden chains onto you. The key thing is you had some outlets that gave a solid “plan B” — something if I had, would make this current situation easier to manage.
I am going through this right now. It’s tough,very tough, much much harder than I thought it would be. However, today I told my immediate coworker that April 16th will be my last day and, I will notify our boss on Friday. I stewed about this decision for weeks, and intellectually knew what I should do, but it was very hard emotionally to do it.
Last night I was out walking to get a little exercise and think, when the “Universe” spoke to me and said: “I opened the door, but you have to walk through it”
Let the next part of the journey begin….
Hi Bill! Thanks for sharing this. It’s very encouraging for me to read of other’s boldness and bravery, especially when mine is nowhere to be found!
I am sure your next leg of the journey will be a rich one. Do keep us posted!
Great article Cubert. I am also suffering from cold-feet-itis. I absolutely agree that continuing to deliver purpose and value is super fun with the added benefit of padding the Stash. One negative personal trait I’ve noticed more recently is I seem to lose patience quickly on the low value job requirements. I don’t want to leave a legacy as the old angry guy. Thanks again for sharing. As always, these communities are great for helping each other down the road to FIRE.
Hey there, Dap! Cold-feel-itis. Love it!
I think I can relate to your feeling of losing patience. There isn’t any benefit to bringing negativity into the office with you. That’s for sure. Glad you found this helpful and for sure, we can share notes on how we’re finding our respective routes to off-ramps.
Stepping away from the job, it’s tough. So tough. I’ve been thinking about it since the past 10 months. Was so ready to do it last September but hung around for another 4 months. Resigned with a flourish 10 days ago! It is so liberating – walking away from it knowing that you could have gone on for OMY but decided to step away anyway, on your terms.
What I’ve found out quickly, and I anticipated this, is that I need something. Anything. Which I suppose is true for most people. I’ve actually started to teach in public school part time. Finding this very rewarding. I will have to write a post on this sometime.
Bottom line, just do it 🙂
Wow! Congrats, NWA! That’s what I’m supposed to do in about 60 days. Well, we’ll see. To your point, it’s the day after that scares me. Your venture into part-time teaching sounds super rewarding – great idea!
Love this post so much. I can only imagine how you’re feeling, but I understand feeling the winter blues and being introspective about all of life’s prospects.
I also thought I was extremely introverted, but lately I’ve found that I am a mix. I want to be with my closest friend group all the time, but leave me out of the big crowds. I don’t need any of that. I think believing we are one way can be damaging to our mental health though, as I’ve slowly found that out the hard way. We should go where our desires take us sometimes.
I’m sure as the seasons change again, you’ll find some clarity. Sometimes there is “the straw that broke the camel’s back” right around the corner that can make a decision easy when it seemed impossible just months ago.
Wishing you all the best in 2020, and I look forward to reading more posts if you find time!
Thank you, Liz! I really appreciate your thoughtful comment.
Clarity is what I could use most right about now. I’m banking on a few things over the next month or so that’ll be incredibly informative as to which path I take. There is one straw just about ready to land!
And thanks for the motivation to write more. I needed that!
All it took was a new VP boss. I gave 5 months notice, staying through the “heavy season” which, except for improving our cash flow, wasn’t necessary. I left for good last October after 30 years.
Not that there weren’t some serious highlights in my career but as you and others have stated, it wasn’t worth the time anymore. Was it a scary decision? Yep. But here’s the bottom line: I’ve never felt more at peace than I have these past few months. My days are physically active and social enough to appease my mildly extroverted personality. Good luck with your decision!
I’m grateful we were (are) frugal.
Hi Knox! Thanks for sharing your experience. I’m truly benefiting from the examples of others who’ve made the leap already. Take care – and stay tuned!