What I Learned in My First Two Months of Self-Employment

The Good, The Bad, and the Reality


It's been two months since I moved from running by business as a freelance side hustle to working on my own full-time from home. And while the experience is fresh in my mind, I want to share some of the things I've discovered in the first nine weeks working on my own. Because although things are (spoiler alert) going well, it's hasn't been without its hiccups, and (spoiler #2), the majority of those hiccups have been created by my own brain.

We hear a lot of of stories of business owners reflecting back on their careers once they've achieved great success. But how often do we hear stories from the trenches, when everything is new and raw, reflections are fresh, and future success is not a given?

We don't get enough of an inside look at what those early days are like from those going through it. Those days when your brain hasn't acclimated to the fact that you don't need to drive to your old job anymore, that you are the head (and entirety) of your management structure, and that you don't have to check in with anyone to take a break. Those days when networking takes on a whole new importance, when the solitary hours in a home office challenge even the most introverted, and when our heads spin with all of the choices there are to make.

I also want to remember these early days for myself.

I've wanted to work for myself for many years, probably longer than I give myself credit for. From my childhood dream of being a horse trainer to my playwriting aspirations in college, none of my dream jobs involved working for a traditional employer. But when you leave school and need to pay your grownup bills (including that glorious student debt), finding a job-job feels imperative. So I transitioned to the business side of the theater world, where I ultimately worked for a decade. In the end, those jobs weren't sustainable; they consumed my energy and demanded days, nights, and weekends. Taking a vacation was an annual challenge. More than ever, I dreamed of finding a way to support myself through self-employment. I explored a lot of ideas, but I guess it wasn't my time yet.

A year and a half ago, when I couldn't maintain the theater lifestyle anymore, I was hired as the director of a coworking space. In order to take that job, however, I needed to make up some lost income. So I started to freelance in social media and digital content work. Very slowly at first -- for 11 months, I was just doing social media management and blogging support for my partner's business. But then, after taking an online business school program last spring, I made a real commitment to this work in order to support other business owners and nonprofit causes. I started to put that message out into the world -- through my website and social media, but also through serendipitous networking and through preexisting relationships -- and I brought on a couple more clients, until I had about 20 hours of ongoing freelance work per week on the side of my Monday-Friday day job.

I went out on my own much later than I would have liked to, but much sooner than I expected to. After several months of juggling multiple clients and my day job, along with weathering some short-term physical health issues, I knew I had to concentrate my energy in one direction. I felt I had made enough of a start with my business that if I committed to that path full-time I would have a good chance of building it up to where I needed.

December 29th was the last day as a W-2 employee. After the New Year's weekend, my partner went off to his office and I sat down at my desk at home and got to work. From there on out, everything depended on my hard work, vision, bravery, and, overarchingly, downright stubbornness to succeed.

Overall, these first two months have gone well, with new clients and prospects, and new volunteer activities that allow me to give back to my community in a way that puts my skills to use.

But January and February weren't without their bumps. Especially January. Turns out that transitioning from traditional employment to self-employment is a weird adjustment. Go figure!

Here are a few observations that might help you in your path. Or, if you've already been down this road, they'll be mighty familiar.


When you freelance on the side, it's easy to keep your work and your services simple and streamlined. You only have so many hours in the week to get the work done, so there's only so much you can offer.

But once more of your hours are freed up for your own business, you have to decide how you want to fill them. Do you want to find more clients and offer them the same set of services until you're booked up? Or do you want to branch into other offerings and revenue streams?

This question hit me hard in the first month on my own. Once my business became my day job, it raised all sorts of questions and made me think about the directions in which I could potentially grow the enterprise. Even though I was only weeks into self-employment, I felt so much self-imposed pressure to make those decisions at that point, lest I grow in the "wrong" direction from the start. That pressure really got to me, and it threatened to distract me from what I needed to be doing at that moment.

A combination of time, conversations with other business owners, and some honest podcast episodes helped me realize that there is no need to rush these decisions. I've been able to relax into those "what more do I want to do?" thoughts with more of a sense of curiosity and grace. That question is as important to me as ever, but I've found some spaciousness within it. 

There will never be an "ultimate" incarnation of your business. Instead, give yourself time and space to grow and develop your work as a natural extension of your own evolution.


This one I was not expecting! I imagined that when I was no longer beholden to an employer's schedule, a rushed commute, and all of the other schedule-ly expectations of traditional employment, I would feel gleeful about it on a daily basis.

What I wasn't prepared for was how long it would take to break the psychological hold that a 9-to-5 schedule had on my brain, and to figure out how to develop a schedule that made sense for my new lifestyle. Rather than necessarily choosing to continue to work a 9-to-5 schedule because it made the most sense, I often feel as if I should maintain that schedule because that's what my brain tells me is a sign of productivity and professionalism.

Although I had been looking forward to having the flexibility to go on mid-day errands, schedule a doctor's appointment at any hour, or just go for a spontaneous afternoon walk, I found that doing those things brought up feelings of guilt, as if I was doing something wrong. You're shirking your responsibilities, Alison! Don't you have more important things to do? When in fact I was getting my work done, just not on a traditional schedule. The freedom with my schedule was exactly what I wanted, it just felt so foreign.

This one's getting easier as the weeks go by and my past life as an employee becomes more distant. But I think it'll still be some time before I can truly sink into enjoying the flexibility of my days without feeling guilty about it or wondering who's judging me for it.


The flip side of having a flexible schedule is that work can bleed into all hours of the day, including weekends. It's likely that your business is going to be on your mind to some degree all the time. Since that can't be avoided, it's important to at least draw boundaries around when and how much you're actively working in your business. If you don't, you're on a quick road to burnout. Not to mention the damage it can do to your relationships.

One of my boundaries is keeping email push notifications off on my phone so that I'm not distracted by work emails in my downtime. Luckily my line of work is generally not full of emergencies and my clients know how to get to me by text or phone if something urgent comes up. I also set boundaries around my energy levels. I'll take a break and come back to my work rather than pushing through exhaustion or brain fog. The results are always better when I rest or reset. 

What boundaries would help give you some breathing room in your business?


This sounds self-explanatory, but it's a crucial point. The more time you spend actively doing client work or physically creating products, manning the counter at your store, or running to the post office to ship orders, the less time you have to market your business, do your budgeting and accounting, and plan your next steps.

If you're someone who likes variety or knows from the start that you want to grow your business well beyond its initial offerings, you'll need to factor in this overhead time. Factor it into your schedule, and factor it into your pricing. You have to be able to make a living for yourself and manage the admin and R&D in a realistic number of hours.

I haven't come up with an ideal "in vs. on" balance yet, so for now it's more about priorities. I would like to be doing more of my own content creation, working on new product development, and practicing new skills. But currently my priorities are with my client work and creating a solid base. I can expand from there.


Slather this lesson across your life. Because unless you're a sociopath with unwavering self-confidence, you're going to encounter a lot of uncomfortable emotions in your self-employment journey, especially at the times when you really have to put yourself out there. And you have to put yourself out there a lot at the beginning.

Whether doubt creeps in when you wonder if anyone will actually pay for your services, or your nerves flare up when you have to pitch a prospective client, challenging feelings will never be far away. They may lie dormant during boom times, but even then questions of "Will this last? Is this too good to be true? How quickly could everything come crashing down?" may begin tickling your brain.

We all have doubts and fears. The good and bad news is, that's normal. That's our primitive brain trying to protect us from the big, scary, risky ideas we have for our lives. But those feelings don't have to be in control. A lot of times, they don't make sense when we look at them critically. So please, look at them critically. Ask, "What's the worst that could happen?" Is it so bad, in the grand scheme of life? Then picture the far side of the situation that worries you. Imagine how good it will feel to have that terrifying pitch behind you, how freeing it will be to finally launch the project you've been anxiously tinkering with for too many months.

As I've grappled with my own fears and doubts, I've gained perspective by recognizing them, identifying their deeper roots, and pushing through them one instance at a time. All I can say is, be scared and do it anyway. Have doubts, but let that voice that says, "What if it works out?" be louder.


I could go on and on.  Self-employment comes with no shortage of lessons, and after two months I'm sure this is just the tip of the iceberg. But if you asked me if I would trade it for the supposed comforts of a "normal" job, I'd say "no way" without hesitation. This is something I've wanted for a long time, and I'm not surprised that there are challenges, even if I'm sometimes surprised by what they are. Despite those hurdles, the future feels open to how I shape it, in a way that it never has before.

I know I'm not alone in these experiences. So now it's your turn:

If you're on a self-employment journey, do these lessons resonate with you? What's the most surprising or striking thing that you learned when you went into business for yourself?

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