If you took a poll in this space, the personal finance/FIRE/retirement/investing/frugality space about what kind of job is the best kind to have, I think I could predict the results. Near the top would be entrepreneurship, which would include owning your own business, free lancing, rental real estate, blogging, YouTube personality, influencer, etc. Near the bottom would be corporate 9 to 5 cubicle dwelling drone. Makes sense doesn’t it? What thoughts fill your dreams when it comes to ideal work? Autonomy, control of your time, purpose, a share of the profits instead of a pittance doled out by a heartless megacorp. How could you ever become the next Bill Gates, Elon Musk or Steve Jobs working in a cubicle doing soul sucking drudge work? But out on your own, making your own rules? The sky is the limit!
I truly get that concept, even though I worked for over thirty years for the same large corporation. But I also have had the privilege of having close friends who owned their own businesses, some quite successful. These weren’t just passing acquaintances but people I’ve been real with, ran marathons with, gone on road trips with and lived life with. So I do have an opinion informed by years of dialogue and observation, about the two ends of the employment scale. An opinion based on actual life experiences and conversations.
When it comes to the corporate 9 to 5, I know it well. For over three decades, starting as summer intern and ending up as the head Fred, you could say I’ve seen it all. I’ve seen some of my peers who languished in that world, they literally dreaded work and lived for the weekend. They had topped out early in their career and were just treading water until they could retire and start living. To me they had sad lives. They were poster children for what is wrong with the rat race. But there were others, ones who had great starts and made it up to middle management, then either from lack of talent or the skewed perception of senior management, just did not have what it takes to keep moving up in the organization. They were making good six figure paychecks but they also were working crazy long hours, were always on call and the constant stress of a demanding job with no future rewards in sight was beating them down. Most of them made it to retirement but sadly some of those did not live to enjoy a long life of leisure and purpose. Whether their early demise was the legacy of work frustration and stress is impossible to know. But I’ve had one widow look me in the eye and tell me my former employer killed her husband.
And then there was another path for a smaller number of fortunate people. I was one of those. Those annoying types that look forward to going into work on Monday mornings because it is one of their most exciting and fulfilling hobbies. Yes, that was me. And I can explain what made work such a kick. I was a nerdy brainy kid in school, and smart teachers and parents guided me toward a career that rewarded those traits, chemical engineering. In college I found I had a knack for understanding how the different disciplines of engineering fit together to solve real world problems. But it was the work world that lit my fuse and unlocked my potential. I had always been intensely competitive but had never had an arena to compete in that suited my talents, until I found it in the work world where I was competing with other young engineers. I had finally found my game, and I loved it! I was given raises, promotions and accolades and just kept moving up the ladder until my pay and responsibilities exceeded my most wishful dreams.
So from my experience the corporate life was not a great one for many but could be incredible for a few. But what about the life of an entrepreneur? Most of my career wasn’t spent in the internet age. I had no experience with my friends being internet influencers or YouTube personalities. They were not life coaches or online marketers. My entrepreneurial friends were people who ran brick and mortar service businesses The three that came to mind were Tom, Chip and Bill, three friends who took the path of running their own companies.
Tom has a trucking business, and it’s a pretty significant operation. He has a lot of employees, truck drivers, office clerical, dispatchers, bookkeepers and maintenance personnel. He operates in multiple cities. He probably has several million invested in tractors and trailers, buildings and equipment. He lives in a very nice house, and like me, his kids are mostly grown and gone. What I’m really trying to compare here is not our actual jobs but the quality of our lives and how our work impacts that. Tom is in total control of his business, he answers to nobody, no boss and no board of directors. He should be stress free, right? I’ve spent a lot of time with Tom, he’s a warm and caring person, a devoted father and has a net worth similar to mine. So he’s wealthy, healthy and in total control of his life. Surely that is way better than being a corporate 9 to 5 indentured servant, right? But no, I don’t think it is. While I always expressed joy in relation to how I felt about my job, Tom usually expresses some level of anxiety. While I was always assured I’d get my six figure compensation no matter how our company performed Tom was always worried about how to keep his company profitable in a very complex world full of risk. He still is even though he’s reached the age I retired. If my company failed or fell out of love with me I could get another job and a raise inside a week. If Tom’s business fails it takes most of his financial stability with it. In fact Tom has been actively trying to sell his operation for years and has not been successful. His kids have no interest in working with him or taking the business over and his competitors would rather see him go under than take over his fleet. And finally while I was able to walk off into an enjoyable and fulfilling retirement on my sixtieth birthday Tom has no exit strategy at all unless he can find someone to buy him out. In short I would never trade my corporate career for Tom’s entrepreneurial one.
Another friend is named Chip. He started up his own service business that serves both residential and commercial customers. He ran it for twenty-five years and then sold it to a national chain for what sounded like a large amount at the time. But for most of the time I’ve known him he owned and ran the business. Chip never seemed to worry as much as Tom but he still felt the constant pressure of competition while running the business. Unlike trucking, the barrier to entry for Chip’s business is fairly low so there were a lot of solo owner/operator competitors driving the price down for his services. Also there was competition from a household name national brand that has a near monopoly nationwide. He did find an exit strategy but now, as an early retired guy who needs a little more money, he doesn’t have an easy way to find good paying part time work. His expertise as a small business owner operator is not very marketable. As a former corporate guy, by comparison, I’ve been able to earn close to $100K every year for the five years I’ve been retired, only working about 8 hours a week. He is currently working nearly forty hours a week in retirement to supplement his investment income. While he successfully executed his exit strategy he came out with less than he feels he now needs. Personally I see his stress level as much higher than mine and much of it has to do with his former life as a small business owner.
Finally there is Bill. Bill worked for others in a couple of jobs but he knew early on he wanted to be his own boss. So he got into a variety of construction and outdoor service industries and later took on commercial and rental real estate. I’d guess Bill is worth at least five times what I am…or maybe he’s on the verge of being broke? Its not clear because Bill has reinvested every cent he has made over the last thirty years and has also used debt to fuel his expansion into new ventures. He is an incredibly hard worker and maybe the kindest guy I’ve ever known. Personally I’m pretty sure he’ll die with the most money but is that really the best measure of success? I would guess he works sixty to seventy hours a week. I think he enjoys it but he also feels the pressure of having a dozen balls in the air at the same time and he also has nobody to take over from him if he ever wants an exit path. While he has equipment and employees, a large part of the value is what is between Bill’s ears and in his stout heart. He’s younger than me, he won’t start thinking about retirement for another 15 years, but when that happens it may be complicated for him. I think when Bill hits 60 he will face a crisis of sorts as he tries to find an exit strategy. My guess is he may just work until he dies. I do think he enjoys work, but it has consumed most of the hours in his life. I would not trade with him.
So what is the conclusion I draw from my career and those of my corporate peers versus my entrepreneurial friends? There isn’t one. I certainly think my path was more fun than that of Tom and Chip’s and at least as interesting and entertaining as Bill’s. But my career was also more fun than that of most of my coworkers’ jobs. I found meaning and purpose in my working career and still do in retirement. I can’t say that was true for most of my corporate teammates or for my entrepreneurial friends. I do think my exit strategy was painless and let me walk away with a seven figure 401K, sizable taxable investments and lots of consulting options. The exit strategy for my business owner friends was and is a high risk venture with no assurance that when they cash out they will have enough. In the corporate world my billion dollar facilities did not have any of my money tied up in them. It was the shareholders who invested the money, I was just paid well to run things. For my three buddies it was all on them. My biggest risk, as long as I kept things legal and compliant, was having to interview for another job if I got fired. Their biggest risk is losing everything and the public embarrassment that goes with it. I don’t say that because there is any shame in failing but because losing a small business you’ve built over decades of sweat and tears has to be incredibly painful compared to simply changing corporate employers.
One measure of life is how the risks you take compare to the rewards you earn. The corporate life has much less risk but caps the rewards you can earn, for most. The entrepreneurial life has no inherent caps but has a staggering failure rate. And cruelly, while early failures don’t cost you much, failing after twenty or more years of building a sizable business has huge downsides both financially and emotionally. I knew I had a skill set that would make me financially comfortable regardless of who I went to work for. That is never guaranteed for entrepreneurs. I never cared about amassing great wealth, just about having enough. There is no regret in me for the safer path I took. I wonder what my friends would say if I put that question to them today?
What about you? Are you planning on playing it safe or taking the risk of entrepreneurship?
Is it even statistically possible to be happy in the corporate world, or was I just an outlier?
Are the risks of having brick and mortar businesses with expensive equipment and employees greater than new economy entrepreneurs face with digital, low capital investment solo businesses?
hi steve. i’m happy having gone the secure employee route. i never made much money but always had jobs rather than a career. i think i picked the wrong company for the past 15 years as my personality type doesn’t typically move up here. like your friends at work some have done well here and some are more frustrated. honestly, if i had landed in the job here i’ve been doing the past 3 i would report it as an overall good experience. i’m about to write a post about what causes a capable and competent person like me cease to care about the company. i show up showered and ready and on time but the “above and beyond” ship has sailed. i hope it doesn’t go down on my permanent record.
i have a friend who is the main principle in his law firm. the exit part is becoming troublesome for him in his 60’s and it isn’t because of money.
My last couple of years at work were not nearly as entertaining as those before. I think I needed that to push me into retirement. I kind of had that same kind of loss of drive at the end of my 9 to 5 career. I sometimes wonder if I’m missing something because I’m not all fired up about any goals right now, I’m just enjoying life.
Steve – an excellent synopsis of the different career paths. In my experience, attitude plays a great role. One method I used to get me over career disappointments is the old saying “it’s not the cards you are dealt but how you played them.” I then looked at the blessings I had and that put the situation in perspective.
Look forward to your next post and have a great weekend.
Oh, I’m living now in Denver for a couple of years so if you are in the area, let me know.
Semper FI,
Luis
That’s a great place to live Luis, I have been there many times. I used to ski a lot, not as much now but we still love hiking in the mountains. Attitude is so important, you nailed it, happiness is not all choice but it has a lot of choice and attitude in it.
I love this quote “One measure of life is how the risks you take compare to the rewards you earn.” We took a risk and ran our own company. The rewards were high, but the workload was tough. I don’t think the weight of owning a company gets talked about enough. It’s a whole lot easier to work for someone else. When you work for an employer you work one job. When you work for yourself you act as HR, legal, and so many other departments all at once. We had a handful of employees and at times it was utterly exhausting.
I don’t think anyone who hasn’t run their own business understands the enormous pressure of being responsible for everything. I only have caught a little of that by seeing the stress and pressure my business owning friends were under. I admire people like you OFG, you really are the backbone of this country. But I also think when you pick a path it should play to your strengths and minimize the competition you face. For a lot of people that turns out to be entrepreneurship, but as a chemical engineer it made more sense for me to work at a megacorp. There are plenty of downsides to the corporate world but they are well known by everyone. Those faced by business owners are too often glossed over.
I’m another successful 9-5 ‘er who got rich from it. But unlike you I reached a saturation point in my mid 40’s where I couldn’t take the bureaucracy anymore. Sounds like you were able to keep engaged in a meaningful way in your job until the end. My job also provided me lots of interesting challenges and fun for much/most of my career, but then it took a hard left into meaningless crap work that I had no interest in doing and was frankly overpaid for. I’m still part time and back to doing slightly more meaningful work, but the seed was sown.
Lastly, I also realized how unhealthy working in an office setting for 40-50 hours a week is. It’s bearable when you’re in your 20’s and 30’s, but as age sets in the detrimental health effects add up and pile on. My health is too important, I won’t let anything compromise it, not for money or anything. Great post.
Dave, it is interesting that I lasted as long as I did. I think it was because there was a detour that hit me in my forties when I became a lobbyist for my owner’s companies. I did that for seven years and it was like starting my career over, except I kept my better than average pay. I was always a show dog at heart and being on TV and YouTube and testifying before Congress were pretty big ego hits for me. Plus spending a ton of time in DC on a lavish expense account was kind of fun for a normally frugal to cheap guy. It felt like a guilty pleasure to wine and dine at a level I’d never pay for myself. Then after that seven years we were bought out by another megacorp and I was put back in charge of everything and given a big boost in compensation. That kept me engaged and excited for a couple of years, then I hit that “meaningless crap” phase. I think it was the two shifts in my career that came out of nowhere that kept me in the game longer than I would have otherwise made it.
This was a great compare and contrast, you captured the weight of being the person in charge well.
One thing I have learned over the years is that businesses based on repeatable systems are saleable as a going concern. Those based largely on networks or cult of personality tend to be less so.
Those networks create a defensive moat, that are difficult to replicate, helping keep competitors at bay while running the business. That same moat becomes the prison walls keeping to owner locked in when it comes time to sell.
Many business owner egos can’t cope with the yielding of control required to automate themselves out of the way, which in turn means it is very difficult for anyone else to viably buy and then run their business after they have gone.
Those are very interesting points Indeedably, I thought about that when I was writing, how some businesses can be sold easily, like my friend Chip’s. While others could be sold off piecemeal like Bill’s and some, like Tom’s might or might not be saleable. The old model of handing down a company to one or more of your kids is not a given anymore either. Your daughter or son might not want to work the farm, or run the trucking company whereas in the past that was almost a lock. I also wondered if every small business founder should be planning their exit from the very start to avoid finding themselves trapped inside that moat later.
Great post, Steve. I was a generally happy employee for several decades until I moved states a few years ago. Then I had to start my own company, but with the huge built-in advantage of initially having a client at the start: my former employer. That client was supposed to be a short-term thing, but it’d ended up being open-ended. So I’ve been very lucky, including by picking up some other work here and there, and experienced both sides of the employee/business owner roles. But I’ve consciously not put myself in a position in which my self-employment gig is a critical pillar holding up me and The Family. One, because I know how stressful that can be, as you so well related in this post. And two, because although my current income is lower than in my last years as an employee, it and the flexibility I have is good. Putting in the extra time and effort to get more work but lose flexibility on my free time frankly isn’t worth it to me. And scaling it up is of precisely no interest to me. I liked being an employee, and would happily go back to being one. In fact, it’s likely that I’ll go do so, in another field, and keep my business (essentially a consulting business) open so that I can have a ready-made, viable side hustle.
FFTP, that’s quite similar to the path I took except I didn’t take it until I retired at sixty, but I immediately began consulting for a couple of company associations that included my former employer. I only do it about eight hours a week but it has paid all our retirement expenses and let our investments grow untouched for the last five years. I had set it up during my career as a plan C, but my plan B flopped so it came in super handy. I could scale it up possibly but at this point in my life more money doesn’t interest me as much as time flexibility, that sounds like the way you feel as well. I never really became a business though, I’m just a contractor legally. And I agree, there isn’t much stress associated with doing something if you know you could get by without it. Thanks for reading and commenting, I always feel like my commenters actually know more about the topics I cover than I do! I really feel a kinship to your path because of the similarities.
I liked this article a lot Steveark – good job. There is a lot to unpack here.
First, I agree with you on the romanticization of entrepreneurship. People don’t realize how demanding it is and how dangerous it can be if there isn’t a clear exit plan. Although still a difficult route, I do believe technology has made it easier if you go the digital route since you don’t need the upfront capital for online businesses.
Second, regarding your work experience, I want to believe that you are not an outlier. But as you know from my personal experience, it seems like you are, at least to me (maybe this is a generational thing). If you take most of my undergrad peers from a state school – the majority are unhappy in corporate America as you would assume. However, more surprising, if you look at my MBA class full of Alphas, you get the same result. I’d say about 90% of my peers when I talk to them, can’t wait to get out of the corporate life and say it is killing them. Of course you have the 10% that are now CFOs and Presidents and love the game. Is the failure of happiness just all of our faults? I don’t know… maybe. But my gut is telling me that more and more people are struggling to find fulfillment and happiness in the corporate environment.
That being said, all of my experience is in Los Angeles, which is over populated, very cut throat and a consumption wonderland. So maybe in Arkansas or less intense areas, more corporate employees are happier? At least, I hope this is the case.
I think I enjoyed my career because it was a stark transition from my early life. I had a great family but I wasn’t a cool kid in high school or college. I so wanted to be that high school quarterback with the cheerleader girlfriend, and not a brainy nerd. But in business I suddenly was a fast mover, the corporate version of the QB. Popular, praised, rewarded. That was steroids for my ego. I began to see myself as a winner and I loved how that felt, I never expected to be a leader yet there I was. I think I loved work because it greatly exceeded my low expectations. Probably that’s the outlier thing, I expected little but got a lot while most expected more and got less. If that makes any sense.
I feel like entrepreneurship runs through my blood since a lot of my family members are small business owners. But I’m still working a corporate job and have done so since graduation from college 20 years ago.
There were definitely a lot of ups and downs with my corporate job. There were years when I wanted to walk away. But I think I am in a comfortable place right now and have no immediate plans to quit.
I do hope that within 10 years, I can walk away from my corporate job and start a business of my own so that I can satisfy that entrepreneur calling ever since I was a younger lad.
SOM, you definitely should do that! Reinventing yourself is like adding years to your life I think. I keep thinking I should do more than my little consulting gig but haven’t pondered that out yet. Any idea what kind of business?
I really enjoyed the comparisons here and I generally agree with them, but I also feel offended by lines such as: “But there were others, ones who had great starts and made it up to middle management, then either from lack of talent or the skewed perception of senior management, just did not have what it takes to keep moving up in the organization.” When I read that line, it seemed like the tone was one of looking down on others. This is offensive to people that take more circuitous routes due to family obligations or any other myriad of issues.
I get that, and I think you are right. I was labeling groups to make a point but the fact is every single person I worked with had their own story. Some sacrificed career goals to be more engaged parents, some found their main focus outside of work. Some wanted to just pay the bills while they planned an entrepreneurial life. I sensed a problem with that part of the post but I was in a hurry to publish and went ahead with it. Thanks, that’s something I need to put more care into.
When I was a lad fresh out of engineering school I was fortunate enough to get a dream job at the employer I fantasized working for since I got to ride in my first classic Corvette. Life was good, I worked my tail off taking on any project they would give me. I learned a ton and was promoted quickly. After year 3 I was at the maximum “level” that I could be promoted to without being a manager and having direct reports. I was told to my face that I was the most qualified hardest working employee but because of quotas for different genders and ethnicity that I shouldn’t count on receiving one of the positions I had earned through hard work for at least 5 years. I was really taken back and confused that my ideal employer maybe wasn’t all it was cracked up to be. Later that same week sitting in a cubicle with one of my mentors having lunch and chatting he said to me “only 17 more years and I can retire”…he was about my age right now and I knew right then and there that a 9-5 corporate job would not be my path in life.
Within a month I had an offer to join a small group buying a tool and die business for less money but my ability to earn and build wealth would fall solely on me. Fast forward through the years of hard work, I was able to build a successful business and retire at 43 with an 8 figure net worth. Six years later because I am an expert in my former field I’m able to have a part time consulting gig that will throw off close to $1M next year alone. So yep, I definitely recommend to young people starting out that if they want to create real wealth in their lives not to choose the path of the corporate world. There is absolutely nothing wrong with it but my friends from college who stayed now have another decade of being chained to a job where as my wife and I are free to travel the world and get busy living.
Not every entrepreneur is able to successfully navigate an exit, but then not every corporate exec makes it to the big bucks either.
Wow, you’ve really killed it! I think you’d have ended up with a high net worth in the corporate world because you are you. But not at 43 and not your kind of wealth. There is little question that the biggest wealth goes to the risk takers, but the question is what is the failure rate, I think it is very high. Congrats, you are the foundation of this economy and I admire people who accomplish what you have, it just wasn’t the path I was geared for.
I really liked this. It gives some interesting perspective to the business-owner glorification that I got out of The Millionaire Next Door.
Owning a business, at least a brick-and-mortar type, seems particularly scary now. Even a well-run and profitable business can suddenly be in deep trouble if it finds itself (or its primary customers) on its governor’s “non-essential” list, whether during another COVID spike or whatever future pandemic is out there. Employees, even those who get furloughed or laid off, don’t stand to lose nearly that much. (Although being an employee with no emergency fund would be pretty scary.)
At the same time, my 9-to-5 office job is now completely work-from-home, with increased autonomy and flexibility, which is what I’ve always wanted it to be. It was the commute, in-office time, and bureaucracy that made me hate my job, not the work itself. Of course, not all jobs are conducive to this. But for those that are, the 9-to-5 suddenly feels like a complete no-brainer. There’s no way in hell I would give this up to go start a business that could have to shut down a few months later through no fault of my own. Unless I was already rich and just doing it as a fun hobby.
It’s unfortunate because entrepreneurship is so incredibly important. I have massive respect for people who take on all the risks and obligations you discussed, but I’m afraid we may see even less of it going forward.
I couldn’t agree more, maybe it had something to do with risk taking in general? I never thought the odds were in my favor to have a business, it was risky even before covid and the digital attack on retail, but now much more so as you aptly point out. Funny though, I’ve skied on terrain where a singe fall would likely injure, possibly kill me. That didn’t bother me, it was an incredible high. But in business I had no desire to live on the edge. To me business was about logic and the odds of winning, having fun, however, that was all about adrenaline.
Your internet car post is closet for comments so I’m posting here. Congrats on a great deal. Never heard of Vroom and went to check out the Toyota RAV4 2020 with built in Android Auto and all its latest safety features. You wrote “2 weeks” turn around. Please clarify. What was the time frame between the time you wired the money and the actual date of receiving car?
It was the time between wiring the money and receiving the car. It’s a little unsettling, I didn’t hear a thing for weight or nine days, then I got a call from the delivery truck driver. He was a little vague on the exact time, kind of like a four hour window. But it worked out great, I still love the car, haven’t found a single blemish or defect that wasn’t clearly identified on their website. Vroom did great for me. Good luck, D.O.G.!
Thank you so much for the clarification. Much appreciated. Two weeks is super fast to arrange for transport and delivery after receiving funds. I’m impressed.
I think all our most of their cars so it of Houston, and that’s only 5 hours away from my location. That might have sped things up.
“Personally I’m pretty sure he’ll die with the most money but is that really the best measure of success?”
I’m going to go with “no” on that one. 🙂
Steve, I appreciate you sharing your perspective in this post of your three buddies. While I’m a good bit younger, I think we could share some similar stories in comparisons.
The difference is that I’d be coming at it from the opposite perspective: analyzing my closest friends who have stuck to (arguably successful) typical career tracks. Fortune 500 corporate consel, government and enterprise software sales at the C level, etc. Heck, the other half of TicTocLife — Jenni, well, Dr. Jenni — is a pharmacist that used to be the manager for her whole branch.
I’m the entrepreneur.
The funny thing is that I’d describe their experiences as being rather difficult even though they’ve found success in the form of money and some notoriety in their respective industries. Still, they’ve missed huge amounts of time away from their family, raising kids, and are occassionally stressed about meeting quotas or crunch times. Occassionally, there’s a larger shakeup within their group that sends shockwaves of job description changes through no fault of their own merit (or without much control).
I left my career track (DC based, digital strategy) back in 2012. I haven’t worked more than perhaps 1,100 or 1,200 hours in a single year since–and I’ve made much more money than I ever did, then. There were (when I wasn’t semiretired) moments of stress: working out a new contract for a project, negotiating–that sort of a thing. But overall, I’m dramatically less stressed and prone to anxiety than I used to be.
Perhaps most importantly, I can just say “no”.
Thanks for the thought provoking post!
Chris, I think you are doing it right. But not many of my generation of irrelevant boomers can seem to figure out how to slow down and smell the roses. I do have some friends who are doctors that cut their hours back to half time, but the guys that run other businesses with employees working for them have not. I was lucky because I had no commute and because I was crazy fast at work and didn’t put in the long hours most of my peers did. I was blessed that I could work much less but still produce more results. I think it might have aggravated some of my superiors that I didn’t live at the plant but in the end they mostly cared about results and I also was pretty stealthy about how much I worked, I think they thought I worked more than I did!