Self Employment Experiment: Month 8 Update

Back in April I left my full time job, and for the past 8 months I’ve been trying self employment. My main goal with this transition was to start living a part-time lifestyle that I am more comfortable with, to get away from the restrictions of office life, while still covering my expenses and *maybe* earning enough to still save some cash in investments every year. My thinking is, if I am able to cover expenses with my variable income for the next 5-10 years, the nest egg I have saved into retirement accounts will be given the chance to grow substantially. Meanwhile, I will be building a life that I enjoy, doing work that I choose, and only working as much as I need or want.

If I had to summarize how it’s going so far, I’d say everything is going really well. There have been challenges balancing work with other endeavors, including the planning and travel time that go into living in our RV full-time, but overall it’s pretty stress-free. I find myself dedicating more time than I thought I might to work, but opportunities have been pretty consistent, and I have been metaphorically making hay while the sun shines. For the past few month my SO has been at work all day M-F, so I’ve been filling my days with work when it’s available. The flexibility has also allowed me to enjoy travel, sleeping in on random weekdays, spending lots of time walking the dog, enjoying afternoon naps, grocery shopping at off-peak times, cooking dinner every night, and more.

The absolute coolest factor about running my business so far is that I have done almost no outreach or advertising. All of my work over the past 8 months came to me organically from people I know and referrals from my professional “network.” I am incredibly proud of and humbled by the fact that people have been consistently reaching out to me to see if I am available. If there is any one piece of advise I have for others who hope to eventually make the transition to self employment, it’s to curate those connections to other people in your intended industry. The network I have built over the past 10 years meeting competitors, colleagues, and collaborators in my industry has been invaluable (and this is coming from an introvert with social anxiety). I also have the amazing luxury that if these work opportunities dry up and things start to look sparse, I can start to do some targeted outreach, or spend more time on my own potentially lucrative projects.

You might be wondering about actual numbers… if I do some back-of-the-envelope math, since leaving my job I think I’ve earned enough to cover about 85% of my expenses. I am having a really challenging time trying to estimate my tax situation this year, but I think that number also includes all taxes due for the year. I believe that 85% coverage is pretty good for my first 8 months of work, especially considering that our expenses have been higher than average in the past few months (we’re staying in the D.C. area, at an expensive campground). There’s also the fact that a number of my first months were quite slow (I was focused on getting out of our house and on the road, and the business was new), and the past few months have really started to pick up.

I don’t want this post to come across as a total brag – so I should elaborate a bit more on the challenges as well. I have struggled pretty badly with procrastination – which I think is rooted in a fear of failure. I also have a bit of imposter syndrome – who am I to put myself out there as an expert consultant?! But I am finding resources to push through these mental blocks, and really forcing myself to make a legitimate effort here. I truly need income and something to keep me busy, so I don’t really have an alternative. Also, people seem happy with my work and continue to hire me, so I must be doing something right.

I have also been going through what I can only describe as an extended “decompression” phase; leaving the world of working full-time for the man can really screw with your motivations, emotions, and sense of purpose. That fog is starting to lift, and some of my motivation to do more creative projects is creeping back. I am definitely excited for the possibilities in the future – and I know working for myself is a key factor in maintaining the freedom that I am enjoying so much.

Despite the challenges, I am making things work, and this experiment is constantly evolving. I know now, more than ever, that I don’t know what the next year holds, but I am pretty confident that I won’t be quitting my new flexible gig any time soon.

Posted in Gap Year Experiment