Freelancing vs. Full Time Jobbing

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January is a tough month for freelancers, at least, specifically, for me. I feel like a sandwich in a panini press: thin on the inside, financially, but feeling the pressure externally. I'm not sure that's a great metaphor but it's still dark out as I write this and I haven't finished my first cup of coffee.  

A friend of mine, who used to work for herself, was asked recently to come onboard a company for a full time job. Freelancers often dream about having a major retainer, to guarantee income and to reduce the amount of marketing time--this is the uber-retainer. She was anxious about returning to the working world, and it made me ponder whether I would return to the 9-5 world for the right opportunity. Here are the pros and cons of each situation, from my perspective thus far:

Pros of working for myself:

  • No commute. I used to drive as much as an hour each way to work. I didn't think this would be a big deal but it really affected my mood and how I approached (literally) my job. My back hurt from all the sitting, I would get ragey if a car was stalled on Lake Shore Drive (done purposefully to bother ME!), by the winter glare reflecting off the road into my eyes, by the windshield fluid running out due to February road salt. I had a garage parking spot which is ostensibly convenient but I actually missed my old bus ride, where I could see people and zone out. Going directly from house, to office, and back felt like I was in a hamster tube. Getting that time back to myself was huge. I still feel a sense of "Boy, I'm glad that's not me," when I hear that traffic on LSD is a disaster, and it's been nearly 5 years since I last had a commute.  
  • No meetings. Did I realize how much I hated meetings until I stopped having to go to them? I'm not sure. All I can say is, damn, I love not going to meetings.  
  • Time to exercise every day.  I used to leave the house before 7 so I could work out at LA Fitness before heading into the office, showering and getting dressed in the locker room, arriving to work sort of clean yet also sweaty from the shower and blow drying my hair. If I forgot a sports bra or a regular bra or my running shoes, then everything was a waste. Now, after the kids are dropped off, I either work out in the basement while watching something like  RuPaul's Drag Race  or  America's Next Top Model,  with no shoes or socks or even sometimes a shirt on (I would never do this at L.A. Fitness), or I go for a run around my neighborhood or down to the lake. I shower and start the day on my own pace. This is as much of my routine now as eating or brushing my teeth and I would have a hard time surrenduring that.  
  • A healthier relationship with food. When I worked at an office, food was a distraction/reward. People brought in  pÄ…czki for Fat Tuesday, food towers for Christmas, catered lunch for meetings and I either ate it or obsessed over how I was not eating it. At home, I don't snack or eat the same way and if I need a distraction I have  plenty. I still love food and am always thinking at least one meal ahead, but I no longer drift around, looking for something unhealthy to scam or worrying over whether I should skip the healthy lunch I brought in and go eat out.  
  • Being my own boss.  I'm a pretty good boss I think. I gave myself permission, for instance, last week to see  Little Women  on a Friday afternoon with my mom. When I think of the liberty of working for myself, nothing encapsulates it more than seeing a movie during the day.  
  • Morning time with the kids. This is funny because on the ground, after many years, this doesn't feel like 'fun' per se--the daily yelling to get your shoes and coat on, the breakfast dishes left on the counter, but at the same time, if you have to choose, morning little kids are better than tired out end-of-day kids. I missed seeing my children in the morning when I used to leave before they'd wake up.
  • Time to do housework and errands. I don't have to cram these into my lunch hour like I used to, or on the weekends. However, this is a double-edged sword (see below).
  • More money. So far. I have actually out-earned what I made at my dayjob and aside from a dip one year, have earned more year after year. This does not come part and parcel with freelancing, though, but it has been validating.
  • Going to Trader Joe's during school hours. You know what I'm talking about. #tinyshoppingcarts
  • Bigger, wilder projects: Last year I turned on my paid subscription newsletter. I helped a cannabis company file their Illinois license. I wrote and submitted a book proposal. I started selling my pitch packet. I haaaaate taking on new projects because they make me so anxious and yet I always say yes and I never regret it. These were the kinds of things I was relieved to have a reason to turn down when I worked full time.  
  • Taking less shit. I fired my first client a few years ago because, being a full timer in the market place, I now know my value. I think if I were part-time freelancing the way I did when I had a dayjob, I'd be more grateful, say yes to unreasonable requests or bad pay more, let the scope of projects creep more without complaining.  

The cons:

  • Irregular income and out of pocket insurance.  This is so stressful, even with the various safety net privileges we have in place (I.E. parents who could help us out if we needed it.) I currently have over $17,000 in invoices due to me. Can you imagine if your full time employer was holding onto that much money? It was also a lot less painful to have my insurance money taken out of my paycheck, plus, my last two employers were major universities and they have primo insurance. I haven't been to see a GP in a few years because after paying $hitloads for things like my kids' teeth cleanings, I'm like, I feel healthy. Maybe they will take my blood at my gynecologist's office, where I am the only patient, I suspect, who does not speak Ukrainian. Plus, when I had jury duty last year, I did not get time off from that, and wouldn't either if I had to take medical or bereavement leave.  
  • It's never enough. This is how I feel right now. In order to combat the January dry spells, all the freelance publications and networks I subscribe to are offering various pitching and marketing challenges. These have worked well for me in the past but for whatever reason, this year they're not reacting well with my mindset. I feel guilty for not doing more, resentful of people who brag about their successes, and helpless, because I get the impression that I could be earning so much more money if I just put my mind to it. Meanwhile this mental setting has obliterated all the pros I listed above. Instead of of focusing on how great it is that I spend more time with my mom, or working out, or my kids, I often feel like I'm not using my time well and am not as serious as I should be.  
  • It's lonely. I'm working on this more in 2020, actively making plans with colleague/friends to get out of the house. I'm a weird combination of introvert/extrovert (I mean, aren't we all?) On the one hand, I get to stay home all day in my cozy house and not deal with people. Yet whenever I go downtown or ride the bus or El, I marvel at all the faces, all the lives right in front of me. I didn't realize how much I crave seeing faces aside from the people I live with or the people at school dropoff.  
  • Being my own boss.  Yes, I put this above as a pro, too. While I like not having performance evaluations or being told I have to track my time, sometimes life is just easier when someone tells you what to do. It's a little terrifying sometimes to know that if I wanted to I could just go crawl into bed and watch TV all day if I wanted to.  
  • I miss work clothes? I used to have cute work clothes and paired my shoes and my bag and and jewelry with my outfits. I don't miss the higher dry cleaning bills and the piles of clothes from changing in and out every day. But there is a whole community of people who only see me in exercise clothes or jeans and express surprise if they see me in a dress or something fitted. I used to look like that all the time. There is, of course, the school of thought that I could just dress for work every day even if I'm at home, but I'm not gonna do that.  
  • Cooking or not cooking. Weirdly I used to prioritize making family dinner more when I worked outside the office, because I felt bad for not being home and thought I needed to do it. I maybe cook a family meal now 3 times a week, if that (last night my husband gave the kids nuked frozen pancakes for dinner; nobody was sad.) It takes time to plan meals, go shopping, prep, cook, wash, and I rarely prioritize that now. I suspect I expose my kids to fewer new foods than other parents do, and we rely a lot on premade meals or repetitive stuff like chili or pasta. My cooking skills and joy have definitely atrophied over time.  
  • Being on-call for the kids/home (see above).  I know parents who work outside the home feel guilty about not being able to pick up their sick kids right away, or can't attend as many school functions or pitching in with community stuff. However it's hard to put up guardrails around work time and family/home time. When I had a direct manager, I could say "My kid is sick; I'm going home" and everyone knew I was out for the day. When you work for yourself you work for many bosses (including yourself) and you can't tell them all that you're off for the day. The same thing happens with school stuff: I know I will never regret chaperoning or helping with a class party, but it's hard not to think of the work I  could  be doing during those times. I got roped into our school fundraiser this year again and while I was complaining about overload, another freelancer said "You can say no. You are in control." I suppose that's the case but to what end? My time is more valuable than other parents'? I am fine with not being helpful? (I do think after this year I'll ask for a year or two off, though.) Similarly, I have to decide every day: am I okay with living in a messy-ass house? Can I wait to take care of my chores until the day is done when I'm tired? Do I want to deal with going to the Verizon store on a weekend when it will be packet, or do I take time out of the workday on a Tuesday?  

The equation of being a full time freelancer is a very complicated one and it's really easy to get sucked into various measures of what is or isn't success. A few days ago I was really ground down, rather than inspired, by everyone's big work plans for 2020, feeling like I'd never be able to dive in like everybody else, unwilling or unable to set concrete goals and a path to them (my goals are usually more like ("Last year was good; let's hope next year's is also good, maybe even a little bit better.") Writing this all out helped me see the bigger picture. Weirdly, the thing I realized I feel most grateful for right now, this second, is not my freedom, my ambition, my financial success or my famiy time, but my ability to exercise every day. So now I'm going to go for a run.