My Worst Self-Employed Nightmare Just Came True

You may have noticed by now that this post is being published later than usual…

I’m sorry for that but it’s because I have some bad news: I got a job again…at the same major bank that I just left a couple months ago. After a 2 month “break,” today was my first day back. I’ve gone from unemployed to underemployed…I sure am moving up in the world!

Here are some things that I would have done differently if given the chance. Hopefully you can learn something from my experiences and incorporate them into your escape plan.

  • I would have had a better plan. I knew what I didn’t want to do (be a teller,) but I didn’t know what I wanted to do instead. I almost did an internship “because it would look good on a resume” but that was basically the only reason why I thought it would be a good idea. Instead, I would have focused on pursuing something that makes me happy that could eventually provide me with enough income to support my fiancée and I.
  • I would have said no to the internship sooner. I decided to decline the internship only 2 days before it was supposed to start but I got a gut feeling that it just wasn’t for me a couple of weeks before. I tried to put up a front and “suck it up” because that’s what I thought I was “supposed” to do. This was the dumbest thing I could have done. I wasn’t being honest with myself and with my fiancée who has supported me through thick and thin. I was transitioning from a job that made me miserable to an internship that probably would have made me miserable. I should have listened to my gut because it would have saved me from lots of headaches.
  • I would have had a couple back-up plans. My mindset was basically internship or nothing. When I quit my job, the internship was the only option that I gave myself. I put all I had into the internship but looking back, I should have had a few ideas I could explore just in case the internship didn’t work out. You know that over-used quote, “don’t put all your eggs in one basket?” Well that’s what I did and it bit me in the ass.
  • I would have gotten to work sooner. Because I didn’t have any back-up plans, I didn’t know what to do. So I did nothing. I wasted a good week or so just playing video games all day. It wasn’t until about a month into my unemployment that I got “serious” and decided that I wanted to spend time writing this blog. Maybe I wouldn’t have had to have gotten a job so soon if I didn’t waste so much time?
  • I would have spent less time feeling sorry for myself. I used to have an agreement with myself: if something bad happens, you have the rest of the day to feel sorry about yourself but come morning, you have to stop and you just have to move on. I didn’t do this so I didn’t realize the awesome opportunity I had in front of me with my new found “free” time. I didn’t get anywhere feeling sorry for myself. Life goes on, the bills won’t wait for you to get your shit together.
  • I would have more money saved up. My fiancée and I had enough money saved up to cover our expenses minus her paychecks for about 6 months. Unfortunately, that didn’t account for anything extra like fun activities and getting a dog. But shit happens. We realized that we didn’t want to put our lives on hold. We decided to “just go with it” and be happy. We didn’t focus on the finances as much as we used to and that made things easier. If I were to do it all over again, I’d have at least 9 months of expenses saved up plus some sort of percentage extra for unplanned expenses/emergencies.

So yeah, I’m pretty bummed that I’m in the current position that I’m in, but it makes me even hungrier to become self-employed. Just like anything, I can look at me getting a job as a blessing or a curse. It’ll be an even bigger challenge now to reach self-employment but if you can learn something from my mishaps and if I can overcome being miserable just for a paycheck, you can too.

I didn’t take the opportunity of all the time I had to get shit done and now I’ll do anything to get it back. It’s a hard lesson that I’m starting to learn. Stay tuned to see how this works out for me.


  1. I’ve contemplated leaving my job MANY times. It normally plays out like this: I decide I cannot live working trapped in a cubicle, I tell my wife that I’m going to quit and work on motorcycles full time and sell motorcycle related apparel. On those last 2 weeks of work I’d start working on motorcycles more and more to transition into that life when I’m no longer putting in time at my day job. The fear of me quitting my day job sets in the first day I’m no longer going to get a paycheck in 2 weeks. I’ve spent days off at my friend’s vintage motorcycle repair shop and it’s not quite how you’d imagine it to be. You’d think you’d get 8 hours of paid work in on any given day but it’s easy to forget the trips to the parts store, traffic, grabbing food, the people that show up to talk shop for 2 hours or more, the friends that arrive early with a 6 pack. Before you tap out for the day you realize you only billed 2-3 hours. FEAR!! REALITY!! It sucks. So I write this from my cubicle hoping I can one day jump ship. Best of luck to you, bud!


    • Thanks man! Yeah we found out the same thing with our motorcycle shop. It especially sucks when you need a certain part and spend an entire afternoon searching for it and it turns out its overseas so you have to wait 2-3 weeks for it to arrive. It’s unfortunately one of those things that you don’t think about/realize until you actually make the leap!


  2. Hey Marc, I’m wondering why you are so focused on being self employed? You seem like a pretty sharp guy with a lot of energy, so I’m sure you can do it if you want. But why do you want to be an entrepreneur?


    • This is a fair question. I’ll follow up with a full blog post sometime but it basically comes down to the freedom; if I control the way I spend my time, I control my life. I decide my schedule, and ultimately how successful I am. I don’t want to have to deal with corporate bullshit, waking up way too early, dealing with unruly customers, following the rules, etc. I hope that helps!


      • This is kind of what I expected which is why I asked. I’m kind of in a middle space between working for the man and being self employed (I’m a contract worker, in other words freelance), so I might be able to give you some perspective here.

        While technically true, I can decide when I want to work, what projects to take, my fee and don’t have to put up with corporate bullshit, it really doesn’t boil down to as much freedom as it sounds. In practice, what happens is that most self employed people I know make less money, work more, and have no idea what things will be like next week or next month. If anything, either route you go, I think you’ll be dealing with many of the same issues. In the end, even if you are your own boss, there’s always someone you answer to, whether it’s clients, customers, vendors, regulators…

        Case in point, I still have to show up at my client’s office most of the time. When I work from home, I end up getting a late start because it’s distracting at home, and I end up playing catchup for the rest of the day, usually working later than I would when I’m working onsite. When I’m at the client’s office and the computer network goes down it takes everybody twice as long to get things done, the client understands, but when that happens at home, they wonder why things took longer than I promised. And then I have to explain – which feels a lot to me like making excuses instead of delivering what I promised.

        Another thing is predictability. If I had a corporate job, I would be able to plan vacations a lot easier. I would know that I have 3 weeks of (paid!!) vacation and sick days on top and could schedule them months in advance. In my case, it’s Friday afternoon and I don’t even know where I’m working next week. Yesterday I didn’t even know if I was working, but luckily I have two companies who want me, so all I have to do is manage that situation without disappointing anybody (booking is a whole other stressful thing). But sometimes I end up having a week or two off without so much as a few hours’ notice. Not too easy to go on fun trips on a few hours notice. When I do plan trips, the cost of the trip is usually a lot less than the cost of the time I could be booking if I just kept working, so I don’t go on too many trips.

        Luckily, I am not fully self employed like a few of my friends. The friends I have who own their own companies end up never being able to leave ‘work at work’ because it follows them everywhere. To a man, the people I know end up doing things like taking client calls from chairlifts on ski vacations and rescheduling international trips around a clients’ whim.

        Of course all of this is sometimes worth it, otherwise they wouldn’t do it. But if I often think about the paths not taken and how things would be different had I followed another path. Often I come to the conclusion that it’s a wash. Certainly there are things that are better but other not so great aspects things that balance things out. If I cold take a corporate job in the field I’m in now, I wouldn’t dismiss it out of hand.

        I don’t want to talk out out of becoming an entrepreneur, but it seems you’ve gone all-in on a few dreams (your motorcycle business and college) and you ended somewhat disillusioned about it afterwards. I think you might want to talk to as many entrepreneurs as you can about how free they really feel to keep your expectations realistic.

        And one more thing. Everybody that I know who became self employed didn’t have a goal to be self employed. Rather, they became entrepreneurs because that was the route they had to take in order to follow their passion. So reasons for being self employed like ‘make my own hours’ have always seemed a little suspect to me. But like I’ve said, you seem pretty driven, so I’m sure you can pull it off if you stick with it. But I just wanted to help manage your expectations so you find yourself in a good place once you you get there.



      • Thanks for an honest response to how it really is. Very valid points to consider…and lots of things that you don’t realize or think about until you actually “make the leap.”

        Lots of people try to make entrepreneurship seem like this glamorous thing that it really isn’t. They don’t focus on things like all hard work, long hours, unpredictability, failures, etc.

        I’ve “grinded” away with the motorcycle shop so I know how “unglamorous” and shitty it can be. I remember working literally 80 hour weeks just putting listings on eBay. It was so monotonous and boring but looking back, I enjoyed that kind of thing better than I do working at a bank at times.

        I was a bit younger when I was “all in” with the motorcycle business so things like benefits, retirement, insurance, etc didn’t concern me but it is definitely something that people should consider when decided to make the “jump.” It’s something that I’m learning is becoming more and more important to me.

        When you are in business you basically become your business. It is always on your mind and you can’t just go on vacation. If you don’t work, you don’t eat. It’s a gift and a curse.

        You’re right; when it comes down to it, it’s basically a wash. Some things are better being self-employed and some things are better working more of a “traditional” job whatever that may be.

        I guess what I’m trying to do and portray with the blog is to open others up to the idea that there are more options out there than going the traditional corporate job route. I was in the position that I finally graduated and had the experience so I thought I’d easily land a “better” job. That wasn’t the case so I became disillusioned and I tried to find out a different way.

        I’m older and a bit wiser and to many of the points that you’ve brought up, I can’t be as risky as I was previously. Hell, I lived at my parents house and they took care of the bills. I had a cushy life but now I have a mortgage, fiance, etc so thank you for really making me think about things.

        I’ve recently had an “aha” moment and started working full-time at the bank in the same position that I was previously in. This way I have the “predictable” income and don’t have to rely as much on being self employed starting out. Starting a business is REALLY difficult so the pressure and stress is already there so add the pressure when you try to turn it into your only source of income “overnight” and it’s a recipe for disaster. Maybe I won’t be “self employed” for a couple of years or maybe never, but I’m in it for the long haul and feel like I owe it to myself and people who come across the blog to give it a genuine shot….to show them how difficult it really is but that it could potentially be sooo worth it.

        Again, thank you for writing your response. It was a lot of good food for thought and I’m better off for it.

        You have an interesting story and it would be awesome to do a “tell your story” feature on you so my readers and I can gain knowledge and insight from someone whose currently trying to make the leap to self employment.

        Let me know what you think. Cheers


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