Self-employed cabin fever

Josh Sherman
7 min read

I was somewhat skeptical that it would happen to me, be after over a year of working for myself and by myself, it finally started to take it’s toll. I had an office so that I would have a place to go during the day to feel like I was “doing something” but that wasn’t enough to keep me excited in the long run. The fact is, working by yourself can be stagnating and I missed the collaborative fireworks that only occur when you work with other people.

I proceeded to work for / by myself for another 6 months after I hit the “wall” before biting the bullet and finding something to occupy me during the day. When it was time to look for a “job” I was fortunate enough to be looking for the right gig and not just something to cover the bills. Unfortunately I found the wrong job in the process and had to deal with quitting after only being on the job for a few weeks. I regret nothing of what transpired, even though it’s not very becoming of me.

Last week I started a new job and am pleased to announce that I am very happy with the situation. Every job has it’s hiccups and this is no exception but the fact remains that I am back to working with talented individuals and am on a development team consisting of two other people so I’m not a one man wrecking crew as I have been in the past. That doesn’t mean that I won’t be attempting to kick more ass than everyone else, it just means that if I have an off day productivity doesn’t slump to zero. I’ve been Atlas before and it’s not ideal for anyone.

Being in an office every day working 9 to 5 has been a culture shock, mostly because I’ve never actually stuck to coming into the office at/before 9am before. In the past I’ve come and gone as I saw fit but am giving it an honest effort this time. I don’t actually believe in the stringent 9 to 5 mentality because development is a creative endeavor and should be approached when you are in the right mindset to absolutely kill it and be your most productive. Sadly, too many people take advantage of working from home and it ends up spoiling opportunities for others. At the end of the day they probably weren’t the right people to hire anyway, but that’s another post all together.

Even though it’s only been a week, I’ve had the opportunity to knock out some code and even got to attend the [most likely] final Front-end Design Conference. If nothing else, this is the first job I’ve had that was willing to foot the bill on conferences without batting an eye at it or trying to figure out how to recoup the time spent out of the office.

Enough about the new gig and more about the cabin fever that set in after being stuck in a silo for the last year and a half, I refer to it as “Silo-itis”. For the first 12 months everything was great because I was catching on a backlog of tasks, some of which were over a year old already. Once that catch up was done and I saw all the gains from doing so, I started to get bored.

I didn’t really have anyone to bounce ideas off of with the exception of the occasional lunch with Justin Davis (which I am greatly appreciative of). I even tried co-working down at the Tampa Bay WaVE Co-working Space to see if that would spark some creativity and/or enthusiasm. Sadly I found the area to be pretty stagnant as it seemed to be mostly a collection of either wantrepreneurs or people with day jobs that were remote and allowed them to co-work with the wantrepreneurs and/or freelancers that held themselves in the same high regard.

To me, it was very much a “we’re the cool kids” type of clique environment. It seemed that some of the companies had some funding but few were what I would consider groundbreaking or revolutionary. The “accelerator” program didn’t seem to have any milestone system in place so the startups that were there didn’t appear to be make many/any gains as there was no pressure of failure. The lack of milestones / goals in an accelerator program could easily be it’s own post that perhaps I’ll touch in the future.

Just a little insight, I actually still have a hard time considering myself to be an entrepreneur because I haven’t built a company that sustains employees. I’ve been fortunate that I have built a passive revenue stream that supports my lifestyle, but it’s not a company, not yet. I felt like most of the occupants wore the “entrepreneur” label on their sleeve regardless of their successes or failures. Perhaps it’s just a “dress for the job you want” approach but the reality is, I want to hang out and interact with people that are doing shit, not people that are talking about it.

So co-working didn’t do it for me. I didn’t bother to explore any other spaces because the WaVE space was close enough for me to bike to which was a big selling point as we went down to one vehicle for a while as this whole “working for myself” timeline played itself out. I would like to think that other co-working spots wouldn’t carry as much of the wantrepreneur-spirit as the would-be accelerator does. I could be mistaken though.

I know a lot of my peers felt that working for myself would mean working all the time, but the reality is I lost my edge with working all of the time because I was able to focus so much of my time on my own projects. I lost that drive to work all night because I was already ahead and wasn’t in the process of trying to get ahead. I got stagnant. I got bored. I wanted to quit my job but I was my boss!

I think this happened not because there wasn’t enough work to do or even because I had grown complacent in life. I think the issue was that I had no one to bounce ideas off of and no one to bounce ideas off of me. We’re social creatures and need those interactions to drive innovation. I didn’t have that and it got boring as hell.

All that being said, a week into this new gig and I’m starting to find my passion again. I’m working at night and trying to squeeze every second out of the day to be productive. I suppose that I thrive on knowing I only have a limited about of time to put into things, mortality and such if you want to get all morbid about it.

Some of my peers think I’m fucking crazy for going back to a day job considering what I’ve built for myself. I know just as many peers that thought I was crazy for leaving the stability of a day job as well. I’ve been blessed with the ability to generate a passive revenue stream and feel like taking advantage of my youth by working a day job again is just icing on the cake. Nobody knows what the future holds, may as well exploit the system while you can, especially if you find that it’s inspiring your other efforts.

I know at least a few people that have worked for themselves only to go back to having a stable day job. Comment below if you’ve been there, I’d love to hear about it!

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About Josh

Husband. Father. Pug dad. Musician. Founder of Holiday API, Head of Engineering and Emoji Specialist at Mailshake, and author of the best damn Lorem Ipsum Library for PHP.

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