What I learned in my first 3 months of business


In September of last year I decided to become self-employed.

Prior to this point, I had been operating as a freelancer, offering graphic design, website design, and marketing services. I would work during the day as part of an inhouse marketing department and then come home, eat some food, and tackle my growing freelance clientele. From what I read, most people who do what I do start out with the ultimate goal of one day being able to work for themselves. This wasn’t what I aimed for though…

Admittedly so, I didn’t always plan on running my own design studio. Working as a graphic designer, website designer, and marketing coordinator for me was the thing I did while I searched for my dream job. It paid for my expenses during university (where I was studying nutrition and food science), it was the thing I fell back on when I realized I wasn’t happy with my education, and it passed the time while I soul searched for the thing I wanted to make as a career.

It wasn’t until a few years into my search for a “dream job” that I was hit by the realization that I had grown to love what I was doing. It allowed me to work in multiple industries, it gave me geographic freedom, and it required both creativity and logic. I had been so focused on finding a different career, that I wasn’t aware the one I was already doing checked off a lot of my requirements.

It was only when I consciously acknowledged that I was happy doing the work I was doing that the idea of being self-employed came up. And when it did, I couldn’t get it out of my head. If you have transitioned from being employed to self-employed (by choice), you probably know what I’m talking about. There was this curiosity of what it would be like to be my own boss, run my own show, and choose the work I wanted to do. I wasn’t completely naïve: I grew up in an entrepreneurial family and I knew the hardships that being a business owner can hold. But perhaps my upbringing was the reason for the feeling. I just knew I had to try it.

So I did what I felt was necessary to move into self-employment: I sold my house, cut my expenses in half, and asked my employer if they wanted to become a client (which they agreed too). In hindsight and compared to a lot of other people’s transition into owning their own business, mine was easy. But as it was happening, it was terrifying. All of a sudden I had 40 hours of my week to fill up with client work, which meant for the first time ever, advertising my services and seeking out clients (I had been living off of referrals at this point).

Even though I have only been in operation full-time for 3 months, it feels like a lifetime. And while the road has been relatively smooth, here are a few things I learned very quickly:

  • Meetings will kill your productivity – I felt like the first month of my business was spent in meetings (with current and potential clients). While I acknowledge the benefit of well-planned meetings, it’s top of my mind for 2018 to limit my meeting availability each week.

  • Working from home is tough and awesome – One day I will feel completely distracted by everything around me (“When is the last time I watered that plant?” or “It’s fine if I just watch one episode of Friends…”) and the next day, I am bursting with gratitude of not having to get out of my pajamas or comb my hair. I’ve tried working out of coffee shops but I like to people watch and that didn’t go over well. For 2018 I am going to seek out workspace rentals that I can use on days I know I need to get out of the home office.

  • Collecting payment is awkward – I don’t know if this is something I will ever feel comfortable doing, but I will say it has gotten easier the more I’ve done it. I also really appreciate my invoicing system that allows me to send email reminders first so that an awkward phone call is my last option (check out Freshbooks if you are looking for an affordable online invoicing software).

  • Setting boundaries is important – I’m sure every freelancer out there has had a client who consistently expects more and more from them. Whether they want you to start attending staff trainings or be on call 24/7, lines can become blurred very quickly and before you know it, you feel like an employee again. Boundaries are important. They have allowed me to stay (partially) sane while working with a handful of clients all at once. Unless I think it’s imperative to the work I will be performing, I don’t offer to attend staff meetings or trainings. At night, I put my cellphone on silent and I’m even looking into the possibility of setting business hours, where I am unreachable (except for emergencies, but lets be honest, I’m not a heart surgeon) during the evenings and (fingers-crossed) weekends.

  • Contracts are important – I haven’t had an issue yet but it’s easy to see why it’s important to have a written document of expectations that both parties agree to. I didn’t see this when I was first starting because most of my clients were literally friends and family. But when I started talking to people I had never met before, it eases the mind to have contracts in place that protect both people if something comes up.

Perhaps the biggest lesson of the last three months has been the importance of consistently reminding myself why I’m doing this. It’s easy to forget the purpose behind being self-employed when you are dealing with a client who is late paying their bill or you feel like you are forced to wear 5 different hats or you can’t go to sleep at night because your brain is on fire with so many thoughts/worries/ideas. It’s easy to long for health care benefits, RRSP matching, and paid lunches. Being an employee has its perks and I can see why a lot of people never move into self-employment during their careers.

For whatever reason, when I was feeling the most insecure about being self-employed, something good would happen. I would get an order for a pre-made logo, I would land an awesome website design project, or an existing client would send me a email, thanking me for the work I’ve done. And during those moments, it always felt like something bigger than me was sending little signs that I was still on the right path.

And just like I love to surround myself with motivational quotes, I also found that writing down my ultimate reasons for being self-employed and referring back to it when things started feeling tough, helped immensely in keeping my motivation up (although sometimes, the only thing that helped was a big glass of wine!).

If you are self-employed and running your own business, how do you set yourself up for success? What do you find yourself doing when times get tough? What is one thing you would tell someone who is considering going out on their own?