What I Learned in the First Year of Working For Myself

It took all of a decade to begin working for myself full time. While at the start of my career, it was unbeknownst to me that I inherently wanted to be an entrepreneur, gradually it became clear with the way I would flesh out, develop, and expand a role to wear a multitude of hats. Even in college, I quickly advanced from an intern to an account executive at a boutique PR firm, heading up a team of four with up to 12 clients at a time; all while attending classes full time and completing homework. It wasn’t until I left that position and became an intern at a local publication that I got my first taste of the freelance lifestyle—and, oh, was it glorious. While I wasn’t paid, I worked on my own time and had free access to endless concerts and festivals. I walked up to venues, and people knew to just let me in (with a +1 at that). Truly, there is no greater ego boost for an adolescent than being seen and respected. My first assignment was to cover a hip hop show, where I, naturally, took it a step further and sat down with the artists at dinner for a video interview. I reveled in the freedom of setting my own boundaries and the exhilaration of attending an event, meeting people, and then sitting down on my laptop editing photos and writing until the wee hours for submission the following morning.

That was the beginning. I knew from then on that I wanted to be a freelance writer and creative. This carried over into living in Costa Rica where I contributed to two local publications, but it wasn’t until years later that I would become an established “professional” when I moved to San Francisco, land of startups. Little did I know that, this is where I would bloom into the leader I needed to become, picking up skills from the flourishing crop of businesses all pulsing with drive and vision. In retrospect, it’s unsurprising that this is the environment in which I would flourish. It was a mishmash of experiences pieced together to form the eclectic set of skills that allowed me to work for myself—feeding the state of mind that had always lingered in the shadows, just waiting to be awakened.

There was always something missing from each of my jobs, a few of which I’d believed would be fulfilling in a multitude of forms. And yet I was let down. Eventually, I knew I was reaching my breaking point. I took another job as stepping stone, knowing that it wasn’t right but didn’t want to miss the opportunity. It was fleeting, but remains an outlet I contribute to weekly and maintain a strong relationship with. From there I reached out to the contacts I had made. I’d laid a foundation, which made it all the easier to take the leap. Fast forward to now, and I’m contributing to a handful of major publications, as well as founding this one, and also have clients where I offer social media, content creation, and marketing services. The takeaway?

Don’t be Afraid to Reach Out

All of my clients now are a result of me simply asking. I’d been talking to a friend about starting a creative agency for years before we both had the time and capacity to actually give it a shot. After working on an editorial feature with a brand, I sent a follow up email telling them how much I enjoyed working with them and offered marketing services—an influencer event to be exact. They were far more interested than I’d expected, and in the end were thrilled with the results. That, is how I found my first client. For many of my long term writing gigs, I’d simply sent an email to the editor with writing samples and a handful of pitches. You never know what will happen until you try.

Community is Everything

You’d be surprised at how much just asking your friends will get you. There’s someone, and often more than just a single someone, who knows someone else that is seeking your services. Let it out into the universe and it will come back to you. It’s through my friends and friends of friends that I’ve been able to learn, grown, and expand. These people have been there to offer guidance, step in to participate, and just support me be it as a sounding board or even just as emotional support to normalize my experience. Truly, there is nothing without community.

Take What You Can Get

When establishing a business, it’s difficult to even fathom taking on work for less pay or even none at all, but in the end it’s been worth it for me to be able to reference notable clients in my portfolio. Once potential clients saw the work I’d done for brands they knew, it made it that much easier to get them on board. Afterwards, you can set your rates.

Know Your Worth

It seems to make sense—a more affordable rate = more clients, but consider the time and effort it takes to actually complete the project. This includes meeting with the client, researching, any editing, etc. While some projects may be fairly efficient to handle, it’s not just that time that the client is paying for, but also your years of experience—the classes you took, the jobs you’ve held, similar projects you’ve worked on. Each of these factors should be considered when determining your rate—and don’t forget about taxes. Also, the more clients you take on, the less time you’ll have—that’s when it makes more sense to prioritize those that appreciate you the most. Having a smaller group of clients who pay better, or even just treat you better, is far more valuable than a large range of clients that skimp on cost and stress you out.

Set Your Limits

Respect your boundaries. It’s all too easy to get caught up in the grind, especially when you’re working for yourself doing something you enjoy. Burnout is real. While it’s a wonderful feeling to give yourself entirely to a project and a client you love, it’s inevitable that the quality of work decreases when you’re overwhelmed, as well as quality of life. It took a long time for me to learn to say no. The biggest reason I decided to work for myself was to have a change in lifestyle so that I could find the time for wellness and things and people that I love. I continue to remind myself that if I don’t take advantage of being able to make my own hours and actually enjoy life, I might as well work a full time job where, in addition to the grind, I would also have health benefits and not have to worry about taxes. The idea is to be able to work where I want to—be it from a cafe, in bed in my PJs, or another country—and take time when I need it. While there are always deadlines, it’s understanding the projects you take on and what they will take from you. Always consider the pros and cons. What makes it worth it or not?

Understand Your Needs

I’ve always been more efficient working alone, and find that I am more focused outside of an office. For many that’s not the case, and perhaps a cafe or co-working space is more suited. There are also times where I find that I am able to tune in more easily and feel more inspired. Generally, that’s in the morning and in the evening. Afternoons are slower and so I will often take a break then. If it’s not due immediately, there’s no point in sitting there trying to force myself to work when I can just take a break and pick it back up when I’m in the right state of mind. Know these things about yourself—the places and environments where you work best, what time of day, distractions, if a fitness class midday boosts your ability to focus, etc.

It’s Not As Glamorous As It Seems

While many people assume that my lifestyle is action packed and on-the-go, I honestly am mostly at home in yoga pants on my laptop for hours. Alone. I do have weekly deadlines and often I find that it’s healthier for me to just knock out work efficiently and then find time to get to the gym, go on a long hike with my dog, or meet friends for dinner. Sometimes, it means if I make time for a social event or even down time, a doctor’s appointment, or to run errands, then I’ll need to work afterwards late into the evening. Yes, my job does come with its perks where I go to events and dinners with some very cool people, but generally I’m heads down, powering through. Working for yourself means you play every role. There isn’t anyone there to set structure for you, remind you of upcoming deadlines, or even give you feedback. While I do receive edits and go over deliverables with clients, there is no team to bounce ideas off of. (Enter community). You are your own boss entirely which requires being able to be self-motivated, and have impulse control. That means when everyone has the holiday weekend off, you might still be working. Or if you take a vacation, you won’t entirely unplug. However, for me, it’s worth the trade off of being able to work when, how, and where I want to.