Working For Fun. 8 Lessons Learned After Financial Independence.

What’s it like working for fun? Coming in to work because you choose to, not because you have to? Is it really all it’s cracked up to be, and most of all – is it possible? Here are my lessons learned about working for fun after early retirement. 

But first… A little backstory. 

Readers of this blog already know this, but here’s the TL;DR of my FIRE life:

  • I reached financial independence by investing in real estate and index funds.
  • I chose to still work part-time because it’s the best side hustle ever.
  • I was asked to temporarily work full time about 6 months ago and I went for it because… 
  1. Having extra money seemed like a good idea. 
  2. It gave me something to do in the winter during the pandemic. 
  3. I wanted to stretch my skills in tech and management. 

Read more about:
Choosing the best trading platform and how to invest.
My Real Estate Portfolio. What it really takes to retire from rentals after 8 years of experience.
Why the best side-hustle is the job you have now.
Surprise! I’m back to working full time.

Yes, I recognize that working for fun is an enviable position, and not everyone gets a chance to do what I do. I get it. But whatever… Where else will you find an opinion piece about someone working for fun? I wanted to show the comparison of how working full-time is different from having a part-time job and how to make the most of it. 

Overall, I have to admit that I miss my part-time work life, but this full-time gig has opened up some interesting avenues for me. 

Working for Fun. 5 Things I Really Enjoyed:

1. Having More Spending Money. 

I’m not an early retiree because I have crazy dough coming in from my investments. I’m an early retiree because I’m really good at living within my means and being frugal – and I have enough money coming from my investments for the lifestyle I want. 

That said, constantly questioning “is it really worth it?” can eventually drain your adventure-bucket when you want to try something new and you’re not sure how it will pan out. So it’s kind of cool to not have to think about it. Last month I bought a new computer – something I probably wouldn’t have done before unless my old one broke. 

I also splurge on virtual assistants for some of my web tasks. That was already a must-have for me, but now I’m more liberal with what I have them do. 

I’m still frugal, but having extra spending money means not wasting brain space on what I consider “worth it.” It gives me that much more brain space to think about other things. 

Read more about:
Living Stingy – why everyone does frugal living wrong
Why FIRE is not about money – it’s about TIME

2. Not Caring About Getting Fired. 

I remember that feeling of not wanting to “rock the boat.” That feeling sucked, and that nagging fear of getting fired for doing the wrong thing was all too real. 

On the flip side, the feeling I have now – not fearing getting fired – is incredible. I can speak my mind and I get to tell people off all the time (in a nice way.) If there’s something you believe in, you can take a stand in a stronger way than ever before. 

There was an opportunity for my company that the exec team didn’t want to bother with because they’d have to pay hundreds of thousands of dollars upfront and wouldn’t see the bright side of the deal for two years. I believed in it. So I told my boss’s boss he was out of his mind. And what happened next? They took my advice about the deal and asked me to work full-time with some upgrades. 

Would I have done that if I feared getting fired? Would I have done that if my finances weren’t where they are now? I doubt it. But I’m working for fun. I know it sounds unfair, but everything’s unfair when you compare yourself to financially independent people. Jobs are no different. 

3. The Drive. 

I’m not talking about my commute. I’m talking about fully committing to something. 

When you work part-time you’re only giving your job part of your brain. In many ways that’s nice, but you don’t have as much skin in the game when it comes to stretching for your goals. 

On the one hand, it’s kind of nice to be able to shrug it off when things aren’t going well. It reduces your overall stress in life when you don’t have super high expectations. Sleep is easy. Prioritizing is easy. You have time for the important but non-urgent life stuff like exercise (and blogging.) 

However, I realized that it’s good to have something to push you. Even if you’re pushing yourself for a product launch that 99% of the world won’t know about. The very nature of corporations is that they’re very good at pushing you (more on that later) but sometimes you need that to avoid drifting away. It’s good to be proud of your accomplishments and it really feels like working for fun. 

Read more about:
10 ways to spend your time to become ULTRA successful

4. New opportunities. 

Here’s something I didn’t expect. When you’re fully in the world of working, work opportunities open up. I’m not even interested in a new job, and I had a dozen headhunters in my inbox last I checked. 

I actually just interviewed for a job in Germany. Why? Just because it might be a fun adventure for my family. It’d be a huge risk if I was worried about my professional future looking forward, but I’m not. I’m working for fun. 

In fact, I remember reading about a similar situation by another finance blogger (Financial Samurai) thinking about working for a startup. Back then I thought he was nuts but now I get it. It’s cool to try new things just for the fun of it. Once you’re really committed to your field, job opportunities just pop up. New countries, new companies, new roles. Everything! It really is working for fun. 

5. Guaranteed Success. 

Surprisingly, this is the biggest factor on my list. 

When you have your own self-driven projects, like a startup, a blog, or whatever else, your success is not guaranteed. And even if you think that’s bullcrap, then at least we can agree that WHEN you’ll succeed is not guaranteed. 

You can put in your blood sweat and tears, you can be passionate, you can be driven, but if no one wants to buy your rock painting kits, you’re out of luck. 

Sidenote, my kids just got a rock painting kit as a gift, and WTF? Is this a business lifehack? It’s just rocks and paint! 

When you’re part of a team your contribution matters. You can feel good about your work regardless of the output. Like, if you’re a programmer and you design an elegant piece of code that solves, I don’t know, world hunger but the project falls apart – you still get to feel good about your work and you still get paid. It’s kind of a good feeling. 

3 Pain Points of Working Full Time Again. 

1. Corporations Really Do Know How to Take a Lot. 

Every corporation I’ve ever worked for has pushed their employees to the limit. After all, more work out of each employee = more profit. I thought I could avoid this because I don’t care about getting fired, but you kind of get swept up in the hustle. 

When all your coworkers are putting in 110%, then you do too. I worked until midnight last night. I guess those PSAs about peer pressure were all true, I just didn’t know they applied to working for fun. 

I’m putting in more hours than I expected to, and to be honest… I’m not a fan of this new arrangement. 

2. It’s Easy to Lose Sight of Your Life Goals. 

I haven’t had a real workout in 2 months and whenever I hear my neighbor’s barbells hit the concrete in his garage I die a little on the inside. 

Sports, hobbies, fun, exercise… They’re all secondary now. To be fair, I have a family with small kids and I always give them my all. But other than that, work generally takes precedence. People depend on me, and if they need something – I want to be there for them. 

When I worked part-time, scheduling in the rest of life was very easy. But my goals have been slipping further and further down my priority list and it’s getting under my skin. Now I question if working for fun was the right call. 

3. I’m Too Normal. 

Working part-time made me a unicorn. (Or kind of like a consultant.) I showed up once or twice a week, cleared some bottlenecks or solved some problems, coached my team on how to proceed, and went about my merry way. I didn’t have to get bogged down by the tasks, the email chains, and all that annoying work stuff

Now is different. I have no excuses and I can’t unload my schedule. Purchaser can’t figure out how Excel works? Circuit boards can’t clear customs? Fire alarms aren’t up to code anymore? That’s my problem now. 

What Would I Recommend? 

So overall working for fun is good. But working for fun part time is better. 

Oh well. Soon I’ll transition back to my part-timeness and will say that I’ve done it twice! And I’ll take you on that FIREescape journey of working for fun and not for the money if you want to join in. 

So What’s Mr. FIREescape Going to Do? 

You’re reading this in real time and for now, I want to see how this plays out. 

When it comes to working for fun full time, the benefits don’t outweigh the costs for me. Yes, the extra cash is nice, but the novelty wears off. And yes, I get to push myself, but that gets annoying when your family has to wait up for you to have dinner. 

I might take advantage of the new opportunities that are presenting themselves, like a new role, a new company, or even a new country just for the adventure of it. Maybe even join a startup team like Financial Samurai because it has a baked-in end date (i.e. IPO payout,) or take 100% of my payment in options just because I can. 

But mostly, I’m looking forward to getting back to my early retirement lifestyle of working part time, being with my family, and running this blog.


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