Is going freelance all it’s cracked up to be? I’m still not sure.
On weighing the cases for and against full-time work, watching my bank account dwindle in real time, and knowing I could be doing more (but wondering if I should)
It’s 2:59 pm on any given weekday. The time of day when I look back and see what I’ve gotten done (usually one or two meals, a workout, some client work, maybe dealing with unloading the dishwasher or starting a load of laundry, maybe even some creative stuff), and also the time when I look ahead and think about what final tasks I can squeeze out of the last two hours of the day.
I don’t have a full 40-hour week, in terms of work, but I feel like I currently have enough work that I can’t dedicate a full day to sending out article pitches or going to the beach on a random Wednesday without planning for it first. I can’t have a full day to write or edit videos or podcast episodes. The things that don’t generate revenue fit between the paid work I have, which is what I wanted and what I expected, but that makes it harder to get done.
At 2:59 pm on any given weekday, I see an empty newsletter draft or a recorded podcast episode that needs editing. And then I look to my left, notice laundry that needs folding or a weekend bag that needs unpacking, and I shift to do that.
I’ve done enough Big Brain stuff today, I say. I’ll try again tomorrow.
Tomorrow comes, I do the stuff that pays me, and the stuff that doesn’t pay me gets harder and harder to prioritize, day after day. The creativity doesn’t spark, the stuff I swore I’d have time to do if I could just get rid of the pesky full-time job doesn’t fit into the time I seem to have, and my priorities are out of whack.
And on top of that, while I’m technically breaking even (making enough money to cover my expenses), I’m still dipping into savings for taxes1 and to buy, well, anything that isn’t an expense. I also have to hustle, find clients, and continuously think about what’s next. Think about money, think about longevity, think about staying relevant.
Before I can help it, I’m singing the words of the great Sharpay Evans:
This is not what I want
this is not what I planned
and I just gotta say
I do not understand…
But then I remember that this is still what I want, at least for the time being.
I think, at least.
No, I know.
I look at the state of AI and the job market, and I very much know it’s not a job market I want to be a part of now, but I can’t help but wonder if going back to steady paid work makes sense sooner rather than later.
I get flashes of the next Great Depression as we get closer and closer to the 100-year mark since the last one. Surely, we’re due for another2? Surely, I should be saving for the inevitable collapse of all things we know and love?
But then I snap back to reality3. Surely, I’m catastrophizing and am being an extremist? Right4?
Surely.
I think about being in a full-time job and having neither the time nor the energy to care about much else. I remember the dread that would not only come on Sundays, but each night before I went to sleep (and so I procrastinated sleep). I remember the skipped workouts, the laundry I could never catch up on, the looming fear of a layoff, due to my own history with layoffs.
I remember signing my full-time offer letter and then realizing I made a mistake two weeks later. I remember thinking it’ll get better after the holidays. I remember crying at my desk5 20 minutes into being back at work after the holidays.
I think, well, this is better than that.
I think, well, if I’m not creating, I might as well be collecting a larger paycheck and the health insurance to match.
But I know there is no comparison. I know the goal, at this point, is to not ever work for someone else.
For where I am in my life, this still feels like the right decision. It still feels dumb, but it’s at least right. I’m still figuring it out, and I think I get frustrated more than anything else that I can’t see clearly.
I remind myself I don’t start working until 10. That I often run or lift weights before I sit down at my computer. That the laundry is the most ‘caught up’ it has ever been, even when there is always laundry to do or fold.
At first that reminder is a sigh of relief. Look at the time I do have, I can breathe.
But then I see all of the places I’m not optimizing, not doing everything I want. I look at the influencers posting about their 5-9s after (or before) their 9-5s. I don’t have a 5-9 or a 9-5 and I still can’t optimize like they can.
I wonder if I’m doing enough. Actually, I know I could be doing more. I promised myself I’d write weekly, I’d get podcast episodes up every two weeks to the day, that I’d reach out to one person on LinkedIn per week. Mondays would be the days I’d glance at the Fractional Job board and Thursdays would be the days I’d look at the The Freelance Writing Network to find additional work to pad my résumé (and my bank account). But the truth is I’ve only done that on two Mondays and one Thursday since April. I send proposals but forget to follow up, and they go nowhere. I have not sent one cold DM on LinkedIn since I quit my job in March.
I told myself I needed to take time to figure it out, but how much time is too much time? How much longer can I tell myself I’ll send the message or update the website?
Perhaps I’m not built for this, perhaps freelance isn’t all it’s cracked up to be, and perhaps society is about to crumble and I really wish I still had that year’s worth of savings.
But then I snap back to reality6. I still believe this was the right move, despite all of that, and I’m willing to spend some more time to learn the answer to these questions.
I think back to 2:59 pm, not on a random weekday but today, when I opened a blank document and just started writing. And how 40 minutes later, at 3:39 pm, I’d written 1,181 words7. So I guess it is all possible, I just think it’s taking me longer than I expected to find my rhythm as someone who is self-employed.
I wonder if I’m over-complicating things (as I tend to do), and if I still just need to be patient, put my best foot forward, and see what comes out, day after day.
my taxes are not my business right now. bad financial advice, but good for my mental health in the present moment.
À la Spanish Flu x COVID…
ope, there goes gravity
...right?!?
I work from home, so thankfully, no audience.
ope, there goes gravity
and then, 35 minutes after that, after some edits and zhuzhing, we’re sitting at a pretty 1,236 (this footnote included).




