Do I Want My Boss’s Job?

*This post may contain affiliate links. Please see my disclosures.

Spending the last seven months away has given me time to reflect on my career: What did I like? What didn’t I enjoy? When did the next rug of the ladder go from a consuming desire to something I’m not interested in? When did financial independence and retiring early come into my mind? The biggest question I’ve thought about though is at what point did I give up my goal of corporate advancement and no longer wanted my boss’s job?

How It Started:

My career destination started to unfold in my second year of college. I took one semester of programming along with being “IT Support” for my hallway and decided that path wasn’t for me. I developed an interest in money in my teenage years, mainly because my immediate family had none while extended family seemed to be better off. The stock market was also in the news constantly. I entered undergraduate in 2000 so I heard about the climb and was watching the fall. Online stock brokerages and day trading became all the rage. This led me over to the business school and I declared my new major to be finance.

I really didn’t know what career I wanted out of the degree, but quickly enjoyed learning more about money. Suddenly math came easy to me because dollar signs were added in front of the numbers. My grades also jumped too, going from being a sub 3.0 student to a decent one inside the major. The school had a newly introduced student managed investment portfolio and I jumped into that group and loved researching individual businesses to invest in (and still do). Somewhere along the way I did my first compound interest calculator to remember figuring out how much I’d have to save and what return it would take to become a millionaire by 40. This planted one my of earliest financial goals.

Enter Banking

The summer before my final year of college was coming around and I had a decision to make for the summer job: Do I keep selling computers and cell phones at Staples or do I try to find something closer to finance? My future in laws point out an ad in the hometown paper for a summer bank teller and I apply.

One thing leads to another, I get the job and somehow miraculously don’t get fired as a bank teller. During my time in that entry level job, I meet a couple people along the way they encouraged me to apply for the company’s college program. It was late 2002 and finance jobs were scarce with the recession and layoffs, so I was happy to have an “in”. While I thought it was a step down from being on Wall Street, this would be a good place to start and they made me an offer of employment which I accepted.

The Initial Job

I was sent out as an entry level commercial banker after training: I was officially a money salesman, loaning money to small businesses and entrepreneurs. This also gave me a quick view of the corporate ladder in a fairly flat organization. If I wanted to go higher, it meant running a sales team (and likely run a couple of larger teams), then make it to an Executive Vice President role and run one of the bank divisions inside the company. Then if I excelled in that role with the same company, made the right connections and performed well, sometime between age 40-50 the possibility would open up to get tapped for top management.

Now I had a clear path. Get a job like my boss and run a sales team. I didn’t see a path in the group I was working in and made a move inside the company three years in. A few people in my training class started hitting the goal and I grinded harder. Reorganizations started after 2009 to reduce costs and my timeline started extending out. Less and less of those positions were available and most of the older generation at the company had concentrated their investments company’s stock and had their retirement plans put on hold. People didn’t retire, the company kept consolidating these jobs, and I didn’t see the pathway that was once there. Would this ever happens? What if it doesn’t? Could I do my current job forever?

Enter FIRE:

We were always frugal and saved well, but I fully dove down the FIRE hole in 2013 when I was convinced that first promotion would never happen. I earned good money, but had the humiliating change of losing a great boss and instead now working for someone that was in my same training class. I knew how close my number was to where Mr. Money Mustache was when he retired and then it was a question of when/how would I do it. I still wanted this next job, but was starting to resign myself to it ever happening. “The future is so bright you’ll need sunglasses” I was told. Yet the future never seemed to happen.

The Big Career Break

The opportunity finally came to take a promotion to go run a market. This involved working closer with our Executive VP and getting to prove what I could do. This quickly led to me following him halfway across the country into a turnaround division and I was off and running in an even bigger job. He was outstanding to work for and always committed the time necessary to develop people.

I was enamored for a while, both with the new job and title plus with the aspiration of what my new boss had earned. He and his wife had an expensive home, he played fancy golf courses, and ran in circles with prominent people and attended every black tie event and could be found at most big sporting events. The boss held celebration events for employees and clients at his home, specifically purchased with the layout necessary to do it. It was a prominent role and he was destined for even bigger jobs inside the company.

He taught me much about leadership, motivating people, and running a division. The truth is I loved running my division, especially when I ran it under his guidance. Goals were simple – Deliver performance in the income statement. Do it consistently over a long period of time and be rewarded. I also realized I was working for a master politician inside the company, as he could get what we needed to get our job done while reducing the friction that got in the way of our success.

My fancy office (The company was always cheap on it’s real estate)

So what changed?

I worked closely with this individual for a year and a half and got an inside glimpse at the personal cost. He put an inordinate amount of time into that role to be successful. Business development, internal politics, talent management, the hours all came at a cost. There was no silver spoon in his background, his dad was an enlisted member of the military who turned to farming in retirement. Something always drove him to outwork the people around him as it was a path to success that was working.

He sacrificed ten years at the first two levels then another eight years at the second level on the hope/bet of making it to executive management. The executive management job would come with even more money but more work. I’m sure he was paid well up until this point, but was that how I wanted to spend the rest of my life? Is that a job I could enjoy and find some balance in life even if I didn’t want the next level? Is 50-60 hours of work in the office plus spending most nights and weekends doing other forms of work really worth it? Would I rather be flying all over the country on weekends networking or would I rather spend time with my spouse? I started to ask myself: What is enough?

The boss did ge the big promotion that he worked so hard for and is now top level management in a Fortune 500 company. A two comma salary, private jet privileges, and 70-80+ hours of work with a calendar in 15min increments. The promotion happened to be for a completely different line of business, so he no longer had influence over my career or the careers of many of the others who worked for him. If I wanted to follow, it would likely be a lateral move to run completely different lines of business. I was happy for him but less confident this was the path for me.

New Boss Arrives

With the prior boss’s departure to a higher level, the his replacement showed up and it was pretty evident the new EVP was not the same caliber. He was a nice person, but generally unqualified for the job. My work conditions moved from a supportive, cut through the BS boss to someone who’s most common line was “These things happen in a large company”. Slowly I get exposed to the level of bureaucracy and lack of competency higher up in the company I was previously immune to. I vividly remember calculating my relocation payback, FIRE number, and calculating how much I’d owe plus the restricted stock I would give up.

If I stayed, how long could I tolerate this? If I moved, I’m signing up for a new three year relocation payback and starting all over. Work would be the hardest in the beginning of a new job if I took another relocation. Did I want to lateral into my third job at that level and start over? None of the options seemed overly appealing and money was becoming less of a motivator, so I chose to stay the course. With the newfound view of the internal politics, I was again questioning the career path of my boss’s job being the next step.

The Medical Scare:

My spouse came down with a mysterious headache during working out in late 2016. This got progressively worse for the next three plus months including nearly ten specialists and a handful of emergency room visits with few answers. She would become fully disabled and not able to be upright for more than 15 minutes without crippling pain and neurological issues. We had a potential diagnosis, but saw specialist after specialist and traveled across the country with minimal result.

This put me almost completely out of work from March through the middle of September for this year, dealing with a viscous cycle of hope and despair as a caretaker while concealing this concern to the outside. The company went on, my team went on, and I was able to put my focus where it needed to be. Money also transitioned to being a tool instead of a goal. My mindset moved from frugal to we were going to travel wherever we needed to go and attempt to solve this mystery.

There was no quick and immediate fix as we expected, but we made some progress and recovery started by September. We would get some improvement month by month, then quarter by quarter, but there was no “back to normal”. The new normal was the slow and grinding process of recovery.

Attempting to “Get Back Into Work”

I slowly eased back into work, but there was no “back” like I was expecting. My brain could not focus on the job with the same level of caring I used to have. Eventually decisions made above me by the new boss impacted some of my team and I had turnover. Turnover was normal in this job, but it hurt when it was avoidable. My new EVP unfortunately measured his success based on how long of a Sunday email he could send, not at how well he could build and reward his team. The incompetency above him became more and more apparent as well and getting a job similar to my boss’s job meant working for that incompetency.

Any love for the game I had was now gone. Was it just that my work culture had turned toxic, or was I damaged goods? Even if I had the love for the game, I no longer desired (and my life situation no longer permitted) me to work 60+ hours a week. Life and perspective had changed. Now it was just a waiting game regarding money and recovery. I had two dates to leave in mind, one was June of 2018 and one was March of 2019. There was a nice retention award due in early 2019 that was worth enough to get my attention even if we didn’t need the money.

We elected evaluate our situation in June and decide then. Recovery was still slow, work was flexible with time off necessary for appointments, and we were into our third year of the out of pocket max on our corporate insurance, so we decided to extend our date out for another nine months. The unexpected problem with this plan was the more I worked, the more disenfranchised I got with the job. I no longer loved the game and resented being there instead of working on a bucket list we had talked about. We were financially independent but it became a both a blessing and a burden: Life is short we had experienced scare at age 35 and were still facing the unknown. Would we really even need/want this money anyways? Why am I putting up with this? I don’t want to climb the ladder and I don’t want my boss’s job anymore. It was no longer my goal

The Lateral Move: Officially Giving It Up The Climb

I eventually navigated a lateral move in my final six months within the same area (no relocation payback) to help the time pass. This was primarily to part ways with the corporate politics and meetings related to leadership, but it had a second benefit: It forced me to finally part with the professional identity I knew. I would no longer be introduced as the President of XYZ market for XYZ Bank. I was giving up both the job I wanted for 10+ years and the officially eliminating the opportunity to ever go higher. Once I pulled this lever, any going back would be starting over. This was removing any hope for the boss’s job and a full commitment to removing the defined career path.

The lateral move only helped some, I still didn’t enjoy the last few months of coming into the office when I should have. This was not going to be my future life and I should have enjoyed “resting and vesting.” Unfortunately I was not cut out for playing a real life version of charades for a job I didn’t want. This wasn’t a career I wanted and parting ways with the life I had experienced and known for the last fifteen years was inevitable. It was an odd feeling every day and concluded with the process of turning in my early retirement notice.

So What Do I Think After Seven Months of Reflection?

Removing myself from both full time work and the only company I’ve known has allowed plenty of time to reflect on what I enjoyed and didn’t enjoy. Running a business segment along with leading, coaching, and developing people was fun. I also worked in a line of business where we provided capital to an entrepreneur to grow, occasionally it was fun watching them use those funds to great success. I’ve missed the intellectual challenge of figuring out a business and a potential deal. There was also the occasional ego boost that came along with prominent positions on not for profit boards a corporate budget plus some personal work could help land.

I realized my tolerance for the “other stuff” faded and then became non existent since I no longer had any career goals for work. We had achieved our financial independence goal and money was barely a motivator. It was easier for me to put up with the stuff I didn’t like in the job because “I needed the money” or “this is a means to and end”. I’ve often wondered how much money would it take to motivate me now? Would triple the paycheck be motivating? I doubt it would change our life much. Our old cars are fine, we eat out as much as we want, and travel where we want to. Maybe it would probably take beachfront home & private jet access type money to interest me, but even then I wonder how long would I need to work for that level of wealth and what kind of jerks might I have to deal with in the process?

Even more than not working for the money, I was also no longer working for “the boss’s job”. My identity was now separated from my professional position at this company. The title and influence provided less fulfillment and more burden on my life. The endless meetings, travel requirements, predictability of conversations that wouldn’t result in any meaningful change had worn on me. On top of this there was the unnecessary friction in the business process inside the company that was not going to change. Enough was really enough.

I know my specific company had turned toxic, but I also occasionally think that it was a company issue and not a me issue. Then I talk to friends who work for other companies in that industry and they remind me about the little tasks I may still not be able to tolerate. Could I deal with the reports? The compliance training? Justifying an expense report? This is on top of not being able to go fishing on a Wednesday afternoon because the weather is good? Would I again need to restrict my travels to a vacation schedule and weekends? I don’t think I could find enough joy in a regular job to offset those negatives.

Wrapping Up:

I wanted to share all of this because I’ve had numerous discussions and questions come to me on this issue. Sometimes its about debate of Working One More Year or choosing to take the Slow Route to Financial Independence. Parting ways with your professional identity may not be easy and it certainly wasn’t easy for me. The processional identity can carry with it security, predictability, and influence. Once I got past the desire for my boss’s job and the prominence that came from higher and higher positions, I was able to slowly part ways with my professional identity.

One very different book I recently read that relates to this topic is Chasing Daylight by Gene O’Kelly. (affiliate link – please see disclosures) He was involuntarily removed from his professional identity with the diagnosis of a terminal illness after making it to the top of a Big 4 accounting firm in the mid 2000s. He wrote this memoir after his diagnosis and is a good read for anyone climbing the corporate ladder wanting to find more balance in their life or struggling with leaving their professional identity.

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10 Replies to “Do I Want My Boss’s Job?”

  1. Great post and great question for younger employees to ask themselves. My boss passed away in his forties and that experience reaffirmed our drive to leave full-time work early. The prospect of One More Year doesn’t appeal to me anymore.

    1. That is one way to receive the shock of the shortness of life relative to a career. Was this at a large company at the time? How long did it take for the company to replace him?

  2. Great post, as usual. It’s always good to see discussion in FI blogs on the emotional / psychological impact of RE, not just the numbers side of it (of which there is only so much that can be said).

    I think that I am in the same boat, so it’s interesting to hear about the struggles you have. Like you, I was a hard charger early in my career, and I successfully “climbed the ladder” in my series of MegaCorps. But then, like you, I had some medical things come up (now mostly resolved) that made me see things a lot differently. It’s a struggle for me, like it seemed to be for you. On the one hand, even though I’ve lost a lot of the motivation I have at work, I still have a very high and very well-paid position that I don’t want to pass up. That said, I also have a family that I’d really, really like to spend more time with, especially now that I am above my initial FI number. Right now the struggle for me is how much above “our number” we go before I go and RE. Absolutely want to hang it up and walk away from the BSD at work, just don’t want to walk away from it too early as I doubt I’ll be able to get back to the level I’m at now…

    1. I appreciate your comments. Parting with a professional identity and the money that comes along with it is hard!
      So many voices in the FI space came from software engineering where I see zero issue with this. For me, carrying that professional title was a validation of how hard I worked to get there. The title was earned. There’s no perfect answer, but I think people overestimate how important the identity/money are and underestimate the cost of working longer than they have to. We only get one shot on this earth.

      If you ever do want to go back to work and need that identity, you now have the flexibility to transition your skills into a not for profit role that could be more flexible.

  3. How is your spouse doing now? Hope she is much better.

    I can relate to this story a lot. In my career as well, there were several times when I was being managed by a terrific boss. The truth is – work is incredibly fun when that happens. I worked hard then – but it wasn’t due to a desire to get to the corner office. A slightly different experience in my current job – my boss was incompetent himself but supportive and left me alone. This was also fun as I had free reign of my department and knew how to handle it.

    Unfortunately the truth about the corporate world is that such situations don’t last. Your boss changes, politics intrudes, organizational culture becomes crappier over time.

    Like you – my patience waned with FI. I achieved FI in Feb this year and am currently putting in my notice (it’s 3 months where I work and the days pass so slowly!)

    1. Apologies for missing this reply initially and congratulations on your notice. How did it go over? Organizations change faster than we usually think they can.

      Mrs. Shirts is doing well, there are some lingering issues that may never resolve, but we are fortunate for her to have the health that she has now.

  4. Interesting post. I’m so sorry about your spouse’s disability/medical issues. I can’t imagine the stress you both have been experiencing. I hope the recovery is ongoing.

    I was just talking to two friends last night about how our ambitions have shriveled in recent years. We are all three in lower level management or right on the cusp in different industries (private banking, Pharma, big 4 accounting director) and in our late 30s. Different life phases too – one married 10 years with a 1 year old, me married 5 years no kids, one about to get engaged. And yet we are all realizing we have “enough” at least for the foreseeable future and are leaning out a bit as far as going after that next promotion.

    I could have my boss’s job when he retires in 1-2 years, but I’d have to work a lot harder to get it, do the political maneuvers, etc. Not to mention take on more stress mentoring and training people, hiring, and leading a good team. Dipping my toe in those waters this year has been fun and challenging, but I’m not sure I want the 100% responsibility. We are already saving 40% of gross so raises do not mean anything to us really. But then again I’m young and don’t want to look back at 45 or 55 and kick myself for not going for the the big job that I can certainly handle.

    Thing is, I could stay just a banker indefinitely and make $200K or so and watch my net worth build. Especially if DH does the same (he’s already leading a commercial banking team and is in line for his boss’s job when he retires too running the division in 3 years or so). But as you have experienced, companies change. The dream job today may not look as rosy in a few years. The stress may not be worth it especially if we have kids or encounter medical challenges like you have.

    Anyway, I really appreciate your perspective and look forward to hearing more about how you navigate early retirement. I do think the identity shift thing would be easier for me as a woman, but too much free time can make me a little existentially nuts, and I’d miss the intellectual stimulation too

    1. Thank you for reading through my ramblings! I think a lot of jobs reach this point where the income relative to work involved is really attractive, then the work increases dramatically by taking up another step. If you’re already disciplined financially, then the only reason to do it is for personal satisfaction.

      That decision is different for everyone. I’m happy to struggle a little in finding creative outlets for my brain in exchange for dumping a toxic work environment.

  5. Thank you for sharing such a powerful story. It’s good to read in your responses to other comments that things have improved for Mrs. Shirts.

    I am “the boss” in our organization, and I lost most of my enthusiasm for the work about two years ago, making it very difficult to be as effective as I would otherwise have been. I initiated a new project that will be very good for the organization, but it’s not made me feel any different. Much of my mental energy is now focused on hitting my target FIRE date, which thankfully is only five (or six) months away.

    My biggest concern is for my team. I sincerely respect them for who they are and how they have helped me everyday to be successful in my job. They tell me how I’ve changed the course of their lives, giving them the opportunity to grow and by introducing them to the principals of FIRE.

    The question the lead on my team is now asking is “Do I want my boss’s job?”. The money is good, but is it worth never being able to mentally switch off – I’ve decided it’s not!

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