6 things I’ve learned being my own boss for 2 years

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From the age of 5, I was always certain on the career path I’d follow: I was going to be a writer. I feel lucky that I’ve never doubted my passion and that my hustle has led to a rewarding profession that’s taken me all over the world. What my kindergarten self couldn’t have predicted is how vastly the market would change by the time I earned a journalism degree. While I once dreamt of being an editor-in-chief of a magazine, my aspirations quickly changed as content became more digitized. Fast forward to the end of my 20s, and I made the choice to quit the comfort of a full-time job — and become my own boss.

To make myself comfortable with this big ‘ole leap of faith, I had a solid year of savings to depend on, just in case it all crumbled. It didn’t — and I actually bring home more bacon today than I ever did being gainfully employed.

However, I wasn’t schooled in the ins-and-outs of running a business. I definitely wasn’t prepared for taking on the hat of accountant and manager, too. Even if you’re a small team of one, there is a major learning curve that comes with being your own boss. Here, my important lessons that could make your path to entrepreneurial success easier:

You have to be flexible

I’ll never forget when my mom visited me while I was living in Peru for a month. We were taking a bus to the train station in Cusco, and I logged on to my computer to send a quick email and submit a story. The road was incredibly bumpy, I had a cold coffee in my hand, and somehow I managed to finish the work. Amazed, my mom asked me “How do you do that?” My answer was clear: practice.

Many people decide to go out on their own in search of freedom, autonomy and the permission to actually do the things they love — and excel in. For me, the ability to travel and still build my bylines was alluring, so I had to be flexible to make the digital nomad lifestyle work. This sometimes meant working strange hours in Asia, taking super-late calls in Europe, or even figuring out how to work from strange places.

Not every freelancer will choose to jet-set, but no matter where you are, there will be hiccups, client demands, and other issues that come up unexpectedly. How you handle these situations can break – or make! – your company.

You have to set boundaries

Truth be told, I never feel super comfortable going on vacation. I’m always anxious about my email, wondering if an editor wants another story from me — or an ASAP revision. I wonder if my SEO clients are asking questions I’m not answering — or if my OOO is working.

For the first year of being on my own, I checked my email all-day and all-night — almost obsessively. I never wanted to drop anything or leave something hanging. But in the process of ‘staying on top of things’ — I was wearing myself out. I couldn’t enjoy dinners with my friends or a movie night with my boyfriend. I decided to test what would happen if I just went away for a weekend, and if for a full week, I didn’t check my email once I closed my laptop for the day.

To my surprise — and delight — my hustle didn’t come crashing down. In fact, nothing changed. Now, I allow myself to take vacations and once I’m done with work for the day — I’m actually done. No more email checking, no more calls, just time to recharge and prepare for the day ahead.

You have to invest in your weaknesses

For me, finances have always been a major learning curve. While I’m an excellent saver — taxes were a totally new ballgame for me as a freelancer. And figuring out how to set up a 401K all by my bad self? Not in my wheelhouse.

After a year of fumbling and not having any true strategy set up, I decided to take a course in business to double-down on the numbers that I needed to be more comfortable with. Though journalism, and writing in any form, come easy to me, these classes did not. Regardless though, I committed to the process and I’m not afraid to ask for help when I need it.

I also outsourced my taxes by hiring an accountant, a lawyer to draft contracts and an assistant to handle research. This makes a big difference in my day-to-day, my bottom line and most importantly, my stress levels.

You have to take the good with the inevitable bad

There are times when I’m able to knock the proposal out of the park and sign a lucrative contract. And then there are times when I completely miss the mark. Some months, I’m booked solid with work — and the next, I’m pitching like crazy. Being your own boss means rolling with the ebbs and flows of business, most of which you can’t predict.

As a type-A overachiever who likes to organize and plan everything, breathing through the low periods has been one of the most difficult and life-changing experiences for me. Through positive self-talk, lots of patience and a budget, I can calm my nerves and settle my anxiety as I wait for the storm to pass and the clouds to break.

You have to be your own strongest advocate

Not only with clients — but with yourself. Especially as a freelancer, many people will try to swindle to save on hiring talent. It took me a while to stand up for my rates, ask for what I was worth and demand it. But once I did, I saw a big shift in my confidence. Not only did clients agree to these rates, but I grew more comfortable saying ‘no’ and negotiating. While that’s definitely part of the process, so is advocating for your own work.

To remain productive and manage a big career, I have to stand up for my time. This means getting to sleep at a decent hour, waking up ready to work and capitalizing on my most productive periods. No boss will hover over me to meet deadlines — that’s purely up to my discretion and motivation.

You can never stop hustling

If you make it, they will come. Sure — but if you just get ‘em there, you still have to take care of them. What few realize about starting their own company or being a solopreneur is that the hustle only gets harder. Because you are fully responsible for your everything, maintaining relationships, networking, staying on task all become that much more important.

I savor the hard work and often thrive off of it, but does it get tiring? Sure. The benefits always outweigh the alternative of a 9-to-5 job — and most of all, I’m happier.