My Life as a 9-5 er


A high: hanging with the cast of “Dexter”.

A low: getting fired (a lot)

There is a segment of the personal finance community (a pretty big segment, actually), that seems to have a problem with the traditional career path, aka the  “9-5”. They bemoan its limitations, politics, lack of freedom, dependency. These anti-“9-5”ers also complain that one needs to spend 40 years in these odious jobs to achieve even a modicum of financial independence –  thus the need for side hustles, entrepreneurship, or, worse case,  grubby desperation tactics like gumroad Ponzi schemes or affiliate sales.

In their worst moments, the job haters even take a further step back and trash the formal education that is usually a prerequisite to a traditional career. Why spend $50k on a fancy degree when you can just self-teach and get by on drop shipping and flipping  (whatever they are)?

Well, I had a traditional 9-5 job for 20+ years. And yes, everything people complain about, in my experience, is true. But there are many, many positives that I never see mentioned – positives that  I think would be pretty hard to achieve without at least a few years in a professional career. So, for this post, I thought it might be useful to at least share one person’s experience of coming in to the office for over two decades.

Below I’ve listed the very worst, and very best, aspects of my career as a 20+ year corporate drone:


The Lows of my 9-5

Most of the complaints about 9-5 jobs have a ring of truth to them. For example:

  • Politics: the worst part of having a corporate career is the politics. There were so many times that I had to do what was politically expedient vs. what was right for the business. And someone else always wanted my job and my department. I was constantly looking over my shoulder.


  • Instability: I don’t know how many times I was fired or laid off. As a colleague once said about a former employer: “They go through Marketing VPs like I go through Pradas!” and I learned that the hard way. My resume was always updated and I learned to get very good at interviewing.


  • Micromanagement: as an entrepreneur in real estate investment, I screw up a lot. But I chalk it up to learning and I get smarter with each mistake. Most companies don’t look at screw ups that way. Failure is minimized (they think) through close management, limited authority, and second guessing every decision. When it does occur, one’s career can be curtailed very quickly.


  • Stress: all this added up to a lot of stress. In fact, I would not call me life 9-5, as it was more like 8-8 most years. I often needed a drink to unwind just so I could sleep after a particularly tough day. I was high strung and had a short fuse most of the time. Since leaving the 9-5, friends and family say I’ve “changed”. Translation: my 9-5 stress was making me kind of a jerk.



The Highs:

I would like to say that in my 20+ year career, I met some brilliant people, worked on or lead some exciting projects, and had many thrilling accomplishments. And all of that is true. But I also understand that for most people, the baser benefits are more relevant, so I will highlight some of the more the vulgar but delightful lifestyle highs of my 9-5:


  • 5 Star travel: I flew all over the world; I ate at Michelin starred restaurants; I stayed at the Four Seasons, and other hotels of similar quality; I only flew business class; I leveraged my job to get into private clubs and access other places that are normally off limits to tourists. One example: at Comic-Con, my team and I ate at the hottest restaurant in town, in a semi-private room next to the cast of “Dexter”.


  • Fantasy housing: I started out at a beachfront apartment with an ocean view in Santa Monica; then moved on to a house in the hills. It was the cheapest on the block, and small (1600 sf), but it had “city to ocean” views. Neighbors included Jimmy Kimmel, Sandra Bullock and Cameron Diaz. Oh, I also lived at the Chateau Marmont for two months: a feat that I believe would be hard to achieve through affiliate sales.


  • Transport: I only drove great cars; starting with a brand new BMW convertible in my 20s and graduating to my beloved Porsche 911, which I still have.


  • Vanity employers: I worked for several high profile, Fortune 50 companies, several of them brand names in the entertainment industry. And I’ll admit it, I got a high off telling people this when they asked about my vocation. Their eyes never glazed over, they usually wanted to hear about what it was really like. I loved never ever having to fear the question “what do you do?”


  • Early retirement: all this cost me a lot. But the kicker is, I still managed to achieve financial independence relatively early (late 40s). I now only work part time out of passion, and spend the rest of my days building a real estate portfolio. So, my 9-5, even with horrific spending habits, still facilitated a kind of FIRE for me.


Now I understand that there are some people out there that could not care less about any of these so-called “highs”. But I suspect that the number who say so are far greater than the number that actually believe it.

Based on my experience, I would urge everyone to consider a 9-5, or at least a high paying one. There are definitely some truly awful aspects. But it may also let you access some benefits that you’ll like never  taste as a solopreneur, side hustler, or (especially!)  extreme saver.


What were your experiences as a 9-5? Any positives? Tell us in the comments below!

2 replies »

  1. I worked a 9 to 5 for over thirty years, loved it! I loved the free travel(often on private jets), all kinds of complimentary boondoggles ranging from ski trips to tennis tournaments, fantastic free food and drink, knowing senator’s, billionaire’s and CEO’s cell numbers and being on television and in the press. And the compensation was outstanding, enough to retire slightly early and never worry about money again. And there was no risk like running your own business has. And in my case not a single layoff, just raises, bonuses and stock rights. As for the negatives, politics aren’t that bad if you always take the high moral ground and if you are smarter than the people who don’t. It was an awesome path for me, I still think it is for many.

Leave a Reply