The Move From Side Hustle to Full Time Career

I never planned on being a calligrapher. I was going to be in fashion and throughout school, university & the early part of my career I was hell-bent on that goal. I worked in fashion retail to get my foot in the door; studied Fashion & Textile Design with Journalism (just in case I decided to work in fashion magazines); launched, showcased and had my own fashion label stocked in boutiques and later worked in fashion buying. I poured my heart into making it happen because there was no alternative, no back up & no second option. And then I came to the shocking realization that I didn’t love the fashion industry, or not the reality of it anyway.

Two years into my fashion-buying career I was positioned in the direction I’d envisioned my life going, but unexpectedly, felt at odds with it. What started out as a smattering of “bad days”, turned into longer periods of unhappiness & disillusionment and by the end of the three years, I was crying every night after work. I poured myself into my work but felt little reward and satisfaction. Those years stripped me of more than my dream; my sense of self-worth was broken.

It took a trip to China to spin me into action. No longer was my dissatisfaction with my job about me, but about the greater global impact my role was having on the environment, and on society. I had a particularly bad day, on which my parents said something along the lines of “Quit tomorrow, we’re not sure why you haven’t already”.

I quit weeks later, with the vague intention of working for a Not-for-profit to give back to the world.

Throughout this period, I was saved by my side hustle. I’d always loved scribbling and throughout some of the hardest periods in the office, I loved going to the flower markets and gifting posies with handwritten notes for colleagues having a tough week. One of my colleagues was an Instagram fashion blogger and threw the idea out there that I should share my writing on Instagram, as a trend for typography seemed to be emerging. I didn’t even know what Instagram was.

To say I’m impetuous would be an understatement. So it will come as no surprise that I had @theblacklinebylauren running by the end of that week.

Coming up with the name was strangely straightforward — I wasn’t thinking of it as a brand or a business so I knew I just had to come up with something catchy. I went for a run, came home with an idea — which was great in my head until I pitched it to my parents and realised it sounded racist — and with a bit of rewording came up with ‘the black line by lauren’. I decided to run ‘theblackline’ together because I liked how it looked. The irony being that the name fits what I do better now than it did back then; as it mimics the way my lines, ideas, thoughts and business vision roll out in one ceaseless flow of black ink.

My first artworks were shameful (and if you don’t believe me…scroll down to the bottom of my feed where they remain as a reminder to everyone that you don’t have to be perfect to begin). I was however, very proud of them at the time! But I was spurred forward by writing quotes or ideas that I needed to hear to get out of the rut I was in. I’d read books by leaders that I looked up to and re-phrase them into five-year-old language to help the wisdom resonate with me.

Over the 9 months that I worked both my full-time job and my side hustle, I began to feel a gradual shift. I fell out of love with my full-time job & “lifelong dream” whilst finding increasing creative fulfillment, direction and love for theblackline. I was starting to get calligraphy jobs from people I didn’t know and I was finding myself very willing to work on theblackline until 11pm — midnight after long, mentally draining days at the office. Then China happened, and ended it all.

From the day I resigned, I was applying for NGO jobs. I wanted to work with the Thankyou Group, A21 Campaign or Compassion. I wanted to change the world and empower the disempowered. I wrote about it on theblackline but I never once envisioned that theblackline could be the medium through which I would work; because after all, in my head, calligraphy was a side-hustle not a full-time job. When anyone at work asked me what I was going to do, I’d say, “Oh I’ll do theblackline for a couple of months to tie me over while I get a real job”

In hindsight, the writing was on the wall. I’d gradually watched this creative project intended to save me turn into small jobs for friends & family to logos & artworks for strangers; I was fine-tuning the mechanics & processes of the business without recognizing it as one.

Though I fell into making my interest my career accidentally, there are a few things I learnt in the process that anyone contemplating doing the same might want to consider.

Moonlighting is a comfortable way of discovering how deep your love is for your side hustle and how viable it is as a moneymaker. It allowed my love for calligraphy to develop into something long lasting rather than all-consuming; I learnt to draw energy or joy from my love of marketing, management, entertaining, flowers, teaching & public speaking through days or periods when the last thing I wanted to do was calligraphy. (And yes, this happens when you make your interest your career — what once seemed cutting edge and exciting can begin to feel mundane or stale when you’re getting similar jobs and you’ve got to continuously find ways to innovate to avoid becoming stagnant!)

Moonlighting also taught me ways of making income from my interest. My full-time job was driven by profit; I was able to apply many observations of what worked and didn’t work in a larger company to my own smaller business. I was learning what to do and what not to do on a daily basis and it was revolutionizing the way I was doing things in my side hustle as it developed from a creative project to a small business.

For many, I think moonlighting may even prove to be a great position to permanently stay in. If you’re risk adverse and find that the balance of two jobs keeps you sane and both drive each other onwards & upwards then by all means, continue in it!

I think it’s also important to know yourself and what you want to achieve from making your interest a full time career. ‘Doing what you love’ is such a vague statement and I don’t believe its limited to making your interest a full time job. For some, it might mean positioning yourself within an established business in a role that includes things that you love to do. For others it might mean having multiple jobs that offset one another or for the less risk adverse, making your interest a full time job and accepting that the trade off is taking on board duties you might not love so much.

In my case, I’d already had a small amount of experience with running my own business and knew I thrived in a high risk, high adrenaline scenario. I knew I loved creating beautiful things, marketing, strategy & planning, managing teams, event planning, developing & maintaining relationships and knew I was going to need help in the area of finances, accounting and technology. I knew from dissatisfaction in my previous role that I had to be contributing positively to the world and wanted to work alongside NGO’s. I also wanted to work in the luxury market (remnant of my fashion dreams!) I knew why I was trading up financial security to make my interest my main squeeze and went on to develop work with both luxury & charitable organizations whilst incorporating all the things I loved doing in my role whilst outsourcing anything I struggled with.

I believe this exercise can also help you recognize other opportunities — if like me, you’re motivated by dissatisfaction in your current role to turn your interest into a career, you may find that doing the above exercise helps you recognize that your skills can be applied to many industries and don’t necessarily have to poured into your interest. For example, with my list of strengths and weaknesses, I could just have easily gone into PR & Communications, Event Planning, and Marketing etc. with some additional study. And who knows, I may still head down that path!

Lastly, I’d recommend developing a trustworthy team around you before you leap. What you’re contemplating will seem like madness to some and those are the last voices you want to have around you when you’re battling self-doubt. You cannot be too careful about who you let speak into your world; and before you take any leap you’re going to want to make sure that the team around you can support you but also offer constructive criticism and advice when needed. My business would never have happened if not for the environment from which I leaped. I had an extremely small vision because I was broken when I began. But my family, church leaders and friends saw more in me at that time than I saw in myself or my dream. Some led by example — taking the leap before me and allowing me to see how they made the transition. Others, were there when I needed encouragement, and reminded me of the wins along the way. Or, when I needed them to, they questioned my motivation for doing things / whether the market needed what I was developing and suggested alternatives; and with the vast range of experience amongst them this often opened me up to opportunities I’d never considered before. An honest, trustworthy & varied sounding board will quickly tell you if your dream needs some serious tweaking before you dive off the edge.

Whatever you decide to do, if you’re dissatisfied in your current role, take some form of action. Weigh up your strengths and weaknesses and assess what else they could be applied to. Find an interest that will offset the gaps in your current job or try making revenue from your current interest and see how that changes your relationship with it. Discuss the successes and failures with your crew and seek advice from those who’ve gone before you.

And if all lights are pointing to a leap off the deep end, know that whatever happens, life isn’t linear.