What I learned in my first 6 months as a full-time freelancer

It’s officially been over 6 months since I shifted my side hustle to my main hustle and made the deep dive into the world of full-time freelancing.

And wow, have I learned a lot.

I think many people (past me included) really romanticize the idea of freelancing. Waking up whenever you want, managing your own time, mid-day pilates classes, and an overall freedom to build your own career.

And sure, those are all perks. But that really doesn’t paint the entire picture of what being a full-time freelancer looks like.

Here’s what I’ve learned:

1. Freedom can be hard to handle

A lot of people look at the freedom of freelancing as one of the major benefits. And don’t get me wrong, it is. I love being able to actively custom-build my own career and pivot whenever I feel compelled to.

But this has a tricky side to it, too.

I’ve constantly been faced with the following dilemma: I can literally do anything that I want to do, so how do I choose?

This has led to multiple existential crises. Which of my strengths do I want to lean into more? What kind of new client work do I want to focus on getting? Do I want to work on expanding my services, or do I want to balance my time with creating new productivity products?

All of these questions rest solely on my shoulders.

And as exciting as this can be, it can roll up into a big ball of overwhelm sometimes.

2. Schedules shouldn’t go out the window

Sleeping in to start your day at 11 am every day, or scheduling lots of mid-day activities feels great… until you find yourself working til late at night every night or on weekends. Or worse, you haven’t worked hard enough to generate the amount of work you need to pay the bills.

When you’re managing your own time, discipline is your lifeline.

This doesn’t mean you need to hold yourself to a strict 9-5, 5 days per week, 8 hours per day schedule. But some kind of consistency is crucial. Although I let myself sleep in some days when I’m just not feeling it and know that I can crank it out the rest of the week, I don’t make it the norm. I have regular working hours that I hold myself accountable to 80% of the time.

But schedules and boundaries go the other way, too.

Since, as a freelancer, your earning potential is essentially limitless, it can be really enticing to work long hours and give yourself no days off. This is one of the easiest ways to inch your way towards burnout. Trust me, I’ve experienced this.

So, although some amount of tough elbow grease and a handful of long days are necessary to build my business, I have learned to put some boundaries in place. I limit the number of days that I work past 5 or 6 pm, and I try to be pretty strict about keeping my weekends open the majority of the time.

3. Efficiency and prioritization are everything

I’m someone who is naturally very self-managing, so I was surprised when I struggled a bit with task management over these last 6 months as a freshly full-time freelancer.

If you’re at a 9-5, it can be easier to tackle things as they pop up. Same with if you’re a side hustler. But as a freelancer, you’re juggling a lot.

I’m doing client work, accounting stuff, internal marketing, client communication, and a whole slew of other things.

So going off a simple checklist that I run through every day isn’t cutting it anymore. I have to be a lot more strategic about when and where I spend my time while I’m working. Or else I risk things not getting done, working longer hours than I should, sacrificing the quality of my work, or some combination of the three.

At the beginning of every week, I lay out all of the tasks that I have on the horizon, including business tasks and client tasks. And I assign each task to a certain day, leaving a few hours of flexibility every day for the random tasks that will inevitably pop up.

But I need to be realistic when I do this. Do I think it’s reasonable to expect myself to write for 8 hours straight in one day? Absolutely not. So I break up any creative focus-intense tasks across multiple days. So instead of trying to write 3 pieces of content in a single day, I just plan ahead to write those across 3 days instead.

And I always think of whether I can break those tasks down into smaller, less intense tasks. For example, I’m a lot more likely to be able to crank out a blog outline at the end of a long day than I am to actually start writing. So maybe I’ll slot my outline in for the day before I write that piece to give myself a head start without trying to run on E, creatively. I love having these less intense tasks, or admin tasks, on hand to fill in when I need what I like to refer to as “active recovery” work between intense sessions.

Another thing to mention here is prioritization. Like I said, I previously tackled things as they came. I can’t shake it with that strategy now. So when something new lands in my lap, my default isn’t to drop everything and start working on it. I decide how urgent it really is, compared to everything else, and then slot it in where appropriate.

(If you can’t tell from this section, your task management system is EVERYTHING. My Notion system is the foundation of my entire creative operations process now)

4. It tests your confidence, but it can also build it

When you’re a 9-5er, you have some amount of separation between your perception of yourself and the success of the company. Because it’s a team effort, you don’t take down times as personally.

But when you’re a freelancer, building your whole business on your own back, the pressure is real. So it can be easy to trick yourself into thinking that you, as a whole, are failing when your business is going through a rough time.

But the flip side also exists. When you’re having a great week, getting lots of good feedback and generating lots of new business, you feel on top of the world.

Overall, my confidence has felt so tied to the success of my freelancing. And although there is a lot of potential upside here, I’ve had to put in some guardrails to protect myself.

It’s been really important to allow myself to disconnect mentally often. On the tough days or weeks, instead of wallowing in self-pity or going into panic problem resolution mode, I force myself to get out. I get in a good workout, I meet up with friends, I lean into a hobby. Reminding myself that I am bigger than my career helps me keep it in perspective that losses in some areas don’t diminish wins in other areas.

5. You’re constantly going to doubt if you made the right choice being a full-time freelancer

I can’t even tell you how many times I’ve panic-applied to full-time jobs in my down time. Only to panic even more when I get interview requests and realize that I don’t actually want the job.

Being a freelancer takes thick skin and grit. It takes patience. It takes organization. Creativity. It’s truly not for the weak. And doubt will get to even the strongest, most confident freelancers. At least, that’s been my experience and that of many of the other freelancers I’ve talked to.

So how do you resolve this? I think it’s just to allow yourself to be flexible and to remain honest with yourself. Do a gut check in these moments of doubt and determine whether it’s a temporary blip or a growing feeling of things not being right.

And the good news is that you don’t have to be married to any decision. If it’s not feeling right, there’s nothing telling you that you can’t get a full-time job if you want. And there’s nothing telling you that you can’t switch up the way that you’re approaching getting business.

I definitely have felt the pressure (mentally and financially) to have it all figured out at every moment and to lean into my inner gIrL bOsS (okay I’m sorry lmao). But just telling myself that I have the freedom to change my mind if I want to has given me an intense amount of peace.