5 Ways Your Life Changes When You Stop Working

Why the infamous ‘millennial quitting’ trend may actually make sense.

Tyler McWilliam
7 min readOct 8, 2018

Today marks the sixth month since I left the work force. Although I have certainly done things since then (least of which finishing a Master’s degree), I have not actually set foot in an office and worked since April. These past six months will never have a place on my resumé — indeed their only legacy will be in its negative space. And while it may seem strange for a 27 year old to just drop out of the races when so many others my age are deep in the thick of making a professional name for themselves, after taking the plunge and living to tell the tale, I don’t think I really regret it. It’s hard to say if leaving the workforce for this long was my intentional choice or the product of circumstance, but life outside of the daily office bubble has definitely come with a few realizations that may not be so obvious for those still in it.

5. Days of the Week Take on Entirely New Meanings

I was never on particularly good terms with Monday; we weren’t outright enemies — in fact Monday could be pretty exciting at times — but it was always inevitable. No matter how I felt or what I wanted to do, Monday was right around the corner, and I needed to abide by its celestial right.

During these six months, I’ve actually come to find that Monday is a pretty solid 24 hour period. In fact, if I had to rank the days of the week, Monday might just come out on top. I’ve been an active stock trader during this period, so my weekly successes and failures weigh completely on my shoulders. If I really wanted to, I could start the week by closing my positions and shutting down my computer — thereby essentially turning Monday off. But I’ve found that over these six months, I’ve met every Monday with a sense of nervous excitement. It’s an opportunity for the unexpected, and a challenge for me to adapt to it. Not only is my relationship with Mondays stronger than ever, I think it may be able to stay that way!

Likewise, Wednesday — trudged through by many with only weekend plans to guide them — has become my bellwether day, a chance to look back at my performance and evaluate the week’s current trajectory, and then create a plan to either sustain my successes or correct my failures. Ironically, for the first time since I lived in the Middle East, Friday has become the most daunting day of the week. It is an unforgiving and objective review of the results of the week. There is no hopeful sugar coating nor shameless flaunting, just a cold figure. Enjoy your weekend, buddy.

Pictured: Me ‘not wanting to talk about’ my performance in the markets last week. A frequent sight.

Weekends, when markets are closed, have actually proven to be quite boring — I usually reserve them for travel days, reading, or calls with friends. They’re not a break from a controlled environment, but rather a big, fat pause button on this grand, self-sustaining, adventure.

4. Time Actually Appreciates in Value

One of the first things I said to myself when I began working full time was “I seem to be here… quite a bit”. I was actually surprised by how my life had completely changed to accommodate massive blocks of working during most days. In fact — my life became more of this strange new job thing than… well, my life.

Achieving personal net worth — an exciting new concept for me — was quickly overshadowed by my free time unexpectedly becoming a far scarcer commodity. After working for a while I did adapt to this and learned how to manage a professional schedule, but still — my time? I was just throwing that stuff around like it was nothing!

“I realize how much of an investment starting a new job will be — and I want to make sure I’m going to love every minute of it!”

I still fail at this, and many times the sun sets far earlier than I had wanted it to, but I realize this, and I better understand the cost of inaction and the value of all this free time. Likewise, I try to dedicate some time every day to look out for new employment opportunities, but now I try to approach job interviews with more questions than the interviewer. I realize how much of an investment starting a new job will be — and I want to make sure I’m going to love every minute of it!

3. Your Bucket List Gets Shattered… and Then Comes Back Stronger

What’s on your bucket list? I can tell you that for mine it was almost exclusively ‘experiences’. I wanted to ride a jet ski in some place or eat some special food, or see some famous thing and, well… those all got checked off quite a bit faster than I expected. When I was a meandering, broke kid in Ohio they certainly seemed to be pretty unobtainable, but once I had the competence, financial means, and time, to start tackling these I knocked them all out one after another. However, contrary to the intended purpose of a bucket list, I did not in fact die after completing the last item*.

*Though at the time I certainly thought I was going to.

It was quite the opposite! Just as quickly as the old items were completed I started to add more, but in contrast these new items were ‘achievements’. Achievements in social leadership, creativity, physical health, and a host of other things that were much more intimidating than the old items. I’m better acquainted with my own shortcomings, and I have a new perspective on the challenge and context required to actually have a shot at completing some of these. Facing the fear and anxiety of living without the security of employment actually helped me realize how much control I can have over who I am, what I do, and how I do it… and it’s made me want the best with all three.

2. Loneliness Becomes an Active Factor

Hey! Here’s a challenge for you — from the time you wake up tomorrow to the time you go to sleep, don’t say a single word to another person! That may sound impossible for most people, but when you work for yourself and travel by yourself, that becomes a very real possibility. And one thing is for certain, no matter how gregarious or introverted you may be — social isolation will drive you utterly crazy.

Day 3 of acute isolation: I have only selfies to keep me company.

It’s easy to take for granted the social benefits of being at work — I certainly did. An office setting isn’t always the best place for friendly chatter, but if you really try, you may discover that everyone at work has a unique perspective and no matter what, there should always be something to talk about. However, when you lose that structure, social contact becomes your own burden to manage. You need to actively allocate time to make sure your days include social interaction in one form or another, and ‘the cashier at the store’ does not count.

1. There’s More to Your Work Than a Paycheck

You go to preschool, and then you go to elementary school, then middle school, high school, university, and then you work, and then you work, and then you work. This is a very clear and established structure, and it’s cliché to reiterate that it’s not the same for everyone. But I think it’s easy to forget that, somewhere between preschool and work, it became your choice to go, your choice to stay, and your choice to leave. By never exercising the third option, it lingers on as the ‘scary option’, a source of fear and anxiety. By confronting it, and not immediately causing your career to go down in flames — you can create a path that may just give you a new sense of perspective.

Pictured: A career going down in flames.

At the end of the day, I do feel like it’s time to get back to work. It’s time to get back to contributing to something that offers opportunities that can have a shot at tackling the new goals these six months have given me. I may have set the bar too low when I was younger or maybe I just got lucky. Yet if I had never left the office and taken the plunge, I never would’ve truly realized or appreciated what I left behind, what I gained, and what the future can hold.

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Tyler McWilliam

I’m a computery guy. I specialize in the business of resilience and dreams.