26 Things I Learned in My First Year of Self Employment as a Full Time Blogger

Photo by Madeleine Laforest

In mid-March 2018, I left my incredible job as a book buyer at Indigo in pursuit of the entrepreneurial life. Initially, I had an online shop called Handled with Care. It was an e-commerce site selling allergy-friendly products at affordable prices. Ultimately I decided to close the shop after a few months as the low margin rendered it unsustainable. A few months later I had sold off as much of the remaining inventory as possible and closed up shop. Despite the financial loss I didn’t feel I had failed; I had learned so so much from that project and it brought me much closer to many members of the food allergy and celiac community. I took a bit of a break in December, taking time to focus on cleaning up my blog, reimagining my approach to content, and of course taking care of my health issues. In January I went hard on blogging, pitching, and setting up my career as a freelance writer and recipe developer.

So why did I leave that sweet 9 - 5 to begin with? It’s kind of crazy, considering it was a dream job for this bookworm (working on custom publishing, buying books, and regular travel), but I always felt I had one foot out the door. I have wanted to focus on my career as a food creative since I was a kid, and my husband and family had been urging me to make the switch for the last few years. It felt good to know that I had their support. At the time I was all about that side hustle life, working long hours at my job and then coming home to blogging, working on my book, planning our wedding, and managing our vacation rental. It doesn’t feel good to only put part of your ambition into a bunch of different things; it feels like you aren’t giving anything your all. On our honeymoon in early April I was suddenly struck by the feeling that I couldn’t go back to the lifestyle I had created. I was always busy, tired, and to be honest not earning enough in any one pursuit to make it worth it. I knew that by the end of our honeymoon I had to decide what to give up, and it was my job. In case you’re wondering, yes I did get a couple speculative questions about whether I was becoming a “stay at home wife” because of the timing. But I didn’t have time for the negativity - I was on to new things.

It’s now been just over a year since the day I quit, and I’m in a reflective mood. So let’s look back together.

These were the most important things I learned…

1.There is no perfect time to quit - you will always be leaving something unfinished

Month after month I kept telling myself that I had to see this project or that project through to the end in order to feel good about leaving. When you are emotionally invested in your work, it’s difficult to envision yourself not being there to see it through. The reality is that the “perfect time” doesn’t really exist. You will likely always be leaving something unfinished. I did ensure that I chose a quieter time of year to leave. In my industry, September - December is the real crunch time and I would not have felt good about picking up and leaving at that point. The spring was a good time to make my exit. To ease the transition, recommend someone to take your place, leave a contacts list for your successor, or make a process document to pass on to your team.

2. You probably won’t snap into a routine right away

The first day of self employment felt like a dream sequence. I thought I knew what my new routine would look like, but instead it was unpredictable. When I woke up, what work I started on first, how much I exercised or went outside, how often I engaged with others. Everything was in a constant state of flux. I even spent a few months at different shared workspaces to see what fit (turns out they weren’t the right fit for me, but they are very valuable to some). I now have some semblance of a routine, but have also embraced the fact that every day is different and doesn’t need to conform to a particular pattern or schedule.

3. It takes time to find your footing

Not working in an office or traditional setting took time to get used to. I got my first job at the age of 12 and have worked at least one job at a time since then, at times working multiple jobs during school. I had been in the corporate world for 7+ years. Being on my own was a sudden and drastic change, and it took some time to find my footing. Be patient with yourself as you find your path. When I start my day now, I know what I need to do for my clients and for myself; it’s a good feeling.

4. My whole wardrobe, and style identity, changed

My closet full of carefully selected tailored pants, black and white blouses, and minimalist dresses suddenly did not fit my lifestyle. I had been a dedicated proponent of the capsule wardrobe; never having to think long on what to wear in the morning, always feeling well dressed, and with the right balance of professional consistency and uniqueness. The day after I left my job, I felt like I had nothing to wear. My life had shifted, and so had the requirements of my attire. Wearing office clothes to the grocery store felt inappropriate. Over time I found my new style identity. During the days I need things that I can move around easily in, that are basic, and that can be covered in flour without issue. I have a selection of robes and lounge pants for at-home work, athleisure for errands, and more visually interesting clothes and occasion-wear for everything else. I take more liberties with my style, and have embraced colour for the first time in over a decade (but cream linen, black, and ecru remain my favorites). I’m still very choosy about what I buy and take forever to select that perfect piece, but the items I welcome into my wardrobe are a total 180 from last year.

5. Learn to lean on yourself

In my old day job, our team was accustomed to getting consensus on things before they were approved. What about this new subject matter? This artist? This signage? A lot of decisions were made as a team, or approved by a senior level person, or consulted on by others. There were existing workflow processes. It was an entrepreneurial environment but one where our work was closely knit. When you go free range, this changes. You won’t have a team to consult with or a senior person who can advise based on their experience. You may ask friends and family for their opinions on things, but quickly realize that not all feedback is meaningful because not everyone shares your point of view or expertise. Learn to lean on yourself to make the best decisions. You only require your own approval.

6. Your family won’t “get” what you do

If you’re like me, you may have a diverse array of clients with projects that vary in scope and expertise. You may not have one job title anymore, so don’t expect anyone to really “get” what you do. I remember telling my dad to download Instagram so he could see what I do, for the most part. Months later I asked my parents if they looked at my Instagram and they said yes they had looked that day he set up the account. Well, I made them look at it again! They didn’t realize it wasn’t a static page. Not everyone will get it, and they don’t have to, so don’t begrudge them for it. It felt good to know that my parents are so proud of me without even knowing exactly what I do.

7. 1 step back, 2 steps forward

You may experience a temporary loss of financial autonomy. When I left my job, I took a big pay cut. But I proceeded anyways because I knew that I could recover that income through my other endeavors, and that the potential for growth and development was bigger. On paper it may be an interim loss of income, but in real life it felt like a loss of autonomy. We live in a consumer culture, and I felt I had less sovereignty or freedom once I was spending money and not earning it. While I did take on a bigger support role at home (waking up earlier with my husband, making us breakfast, keeping the house in order), I wasn’t taken advantage of by those around me, the knowledge of which strengthened my personal relationships.

8. The guilt.

For the first few months I felt a sense of guilt. Guilt that I left such a great and unique job, guilt that I took a big pay cut, guilt that I got to be in the comfort of my home while others were at work, guilt that I didn’t succeed right away, guilt that my health took a turn. I kept worrying that I’d wake up and it was all a dream. It was only after talking about it with others that I realized the feeling is not uncommon.

9. You’re no longer in demand in the same way

At your job you’re usually the expert at something. Or you’re the new learner of something. Your colleagues may identify you as the person who is so knowledgeable about blank, and they come to you for assistance. Your coworkers count on you to be a a team player, and you have to own your projects and tasks. Your boss has expectations of you. If you don’t show up or don’t pull your weight it will have repercussions for others. However, when you work for yourself, no one really has any expectations except that you earn money in whatever way you choose to get it. No one asks for a status update, no one knows if you won or lost a contract, no one needs you to work as a team. This feeling can be empowering if you look at it with the right lens. Maybe you’re the expert at something new, for a new audience or team. You’ve become your own boss so you should have expectations of yourself. You should give yourself status reports and reflect on your performance. You should hold yourself accountable.

10. People have more respect for you for making tough but necessary decisions as opposed to saying everything is fine when it’s not

When I closed my online shop, I knew it was the right decision without a doubt. But that didn’t mean I wasn’t a little embarrassed about it. To my surprise, friends and family seemed to respect me more for having made a tough, smart decision than if I had continued to run the shop at a loss.

11. I can’t wait to start work in the morning

No longer do I snooze my alarm a million times until there are just barely enough minutes left for me to brush my teeth, throw my makeup on, and grab some items from my capsule wardrobe. I was a chronic always-a-bit-late person. Now I wake up early and begin working while I drink my coffee and eat my breakfast - which means I often start work at 7:30 am. I don’t like to waste any time and I’m excited about the day ahead. That’s how I know I have pursued my passion!

12. If a pasta dish does not have a red sauce, people will call it pasta salad and there’s nothing you can do about it.

The moral - people often miss the point. They scroll quickly and make assumptions. Not every person who interacted with your post will read the whole caption. I’m the subject of many assumptions - that I’m vegan, that I have celiac disease, that I’m intolerant to foods or that my allergies are not severe, that my allergies can be “cured” through a garden variety of “therapies” (someone once told me my allergy, an autoimmune disease, could be cured through specific yoga poses. I’m not kidding.). Once you publish content you have no control over how people will interact with it or respond to it. You might post about your anxiety disorder and someone will comment that your hair looks pretty. Don’t take it personally, this is just part of blogging. Not everyone knows how to respond to a serious post, or cares what type of pasta is behind the lens. If an assumption is made about my health or person, I may choose to correct it, but otherwise that’s just life.

13. Freelancing is not a straight line - you will take on a diverse portfolio of work

Currently, I work with several food companies to generate content and recipes, I consult for a children’s charity, and I am promoting my book. I’ve also written for an online home and design magazine, among other things. Despite having a central focus, diverse opportunities may come your way and draw from a different area of your expertise and experience. It’s one of the things I love most about this job!

14. Streamline

You only have so much time and can only put so much of yourself into each of your endeavors. Overextending yourself can happen quicker than you can say RSVP. Narrowing my focus and cutting out the excess has allowed me to immerse myself in things I really care about (see above), and to get more out of those things. I’m not nearly as busy as I used to be, my schedule is not packed, and I’m loving it. It has allowed me more time to finesse and perfect my creative work. I feel I’m now getting more out of committing to less.

15. You might not relate to your friend’s and family’s work woes anymore

That doesn’t mean I’ve stopped listening though. Everyone’s woes are valid as they pertain to each of our own lives, so they should not be trivialized. But I do find it difficult to relate at times. A friend or family member may be telling me about an issue with their annoying colleague, while I’m thinking about how I’ve had to chase accounts for my pay cheques. Working for yourself doesn’t mean you get to escape politics entirely, but maybe that you are exposed to politics in a different way.

16. I’m selective about which events I attend

It seems there is always a media/blogger event happening in Toronto, and it might feel like you’re missing out if you don’t attend. Product launches, blogger events, entrepreneur events, networking events, etc. These can be useful for networking or advice, or just for socializing (meeting online friends in real life), but you don’t have to go to every single thing. I’ve become a lot more particular about what I attend. Does this appeal to my readers (and if so, how/will I choose to share it on social?)? In what way will it enhance my career or education? Is it a valuable use of my time and money? Do the speakers appeal to me? Is the location accessible for me? For example, I’ve shifted my focus to events within the food and food allergy community over the last year.

17. I hear the phrases “hey guys” and “so I’m just going to walk you through…” at least 100 times a day on Instagram. Let’s please find new things to say.

Please. I beg you.

18. Scoring contracts on your own is extremely rewarding

There’s nothing like the feeling of putting together a pitch and a media kit, targeting specific companies, and signing that contract when they want to work with you. It feels incredible. As a writer, I am used to rejection; it’s a big part of the job. So when you land a deal, especially one you coveted, it feels incredible.

19. When all else fails, toss out some oozing chocolate food porn

Some days the algorithm screws you. Some days your content just doesn’t stick. There’s a fine balance between sharing new concepts, your take on trends, and the tried and true classics. Sometimes you miss your mark. If you never miss it, that means you probably aren’t tossing enough out there to see what sticks. But when you do miss, know that you can always play around with what you know works. Like oozing chocolate. People love to see melted chocolate on their feed.

20. Your content doesn’t always have to be groundbreaking, but it should be authentic

Not every recipe (or outfit, or design, or whatever your creative medium is) has to be something that no one has ever thought of before. You can share a picture or a review of an existing recipe so long as you credit it, or you can just go for it and make your own version of a classic dish. What matters is that it’s authentic to who you are! With social media that needs to be updated so frequently, it’s not always possible to share a groundbreaking revelation every day if you’re a one person show. People will be happy to hear from you!

21. Being a lone wolf works in my favor

It’s a big jump to go from an office environment to working at home alone. It can be a little quiet at times, but overall I really enjoy it. When I need people contact I go outside. You get to work within your own parameters and schedule. I think one of the reasons that I didn’t click with shared workspaces is that I prefer to be by myself. Being a lone wolf, or an extroverted introvert, is certainly suited to my lifestyle.

22. Say no to lunch

A few years ago I read this Manrepeller interview with Stephanie Danler where she explained that she has to “say no to lunch” in order to get work done. It stuck with me, and as though it was foreshadowed by the infinite wisdom of MR, I found myself in the same situation last year. When you are self employed people sometimes assume that you have nothing to do, or that you lay in your undies on the couch all day watching reruns and eating leftovers. And while I do prefer to eat my leftovers on the couch in my skivvies, it is not what I do all day. Lunch quickly turns into shopping, coffee quickly turns into lunch, all of these things can turn into “just dropping something off” or doing an errand for so-and-so. You have shit to do. Be selective about lunches.

23. You are stronger and more resilient than you think, both mentally and physically

I used to feel so frail all the time. A year ago, I thought I was averse to exercising. I hated driving because I thought I was bad at it. There were a lot of things that I thought I wasn’t good enough at or strong enough for. That is, until I decided to change my attitude and to have no patience for people who don’t uplift. Turns out I can do a lot more than I ever gave myself credit for, and I don’t need help nearly as much as I used to think I did. I shed a shell that I didn’t even know I was wearing, and it was empowering.

24. There’s a difference between “over-curating” your feed, and curating for what is a good fit

As a blogger you are offered a lot of things “for free”. Mainly, product samples, guest posts, and tickets to industry events and launches. In the beginning, it’s exciting and you want to say yes to everything because they are all new opportunities. But your feed can quickly become an ad page if you aren’t careful, and no one wants to follow that. The reason I only do paid work is because I am very choosy about who I work with, and I put my all into every recipe, photo, and piece of content I generate. This is curation, in a good way. It’s meaningful content that’s real, authentic, valuable, and something I care about and feel my readers would benefit from. What I don’t curate is my life. I post about anxiety, difficulties of living with food allergy, photos on my stories when I’m not feeling thin or hot, videos of myself in my robe without any makeup on, videos of myself struggling to walk home after a barre class. Over-curating is when you strip your real life from your posts and present a distorted and fake version of yourself. “Curate” doesn’t have to be a dirty word, so long as you do it in a way that is authentic and meaningful.

25. It was an unforeseen “Eat Pray Love” year

My year of change, growth, and self-discovery. I returned to my roots in ways I could not have imagined; to the things that made me happiest for as long as I could remember. I cooked all day, I ate with family and friends, I cooked for family and friends. I started entertaining for fun again. I looked through my old handwritten cookbooks and food photos from 20 years ago. I watched home videos and old cartoons. I reconnected with people in my community. I spent time with my books, with myself, at the cottage, with my parents, at the market, outside the homes my grandparents and parents grew up in. I shed a lot, and grew a ton. It was my Eat, Pray, Love year.

26. Oh yeah, trolls.

Once you get used to reading troll comments, you become desensitized to it pretty quickly. Whenever I have an article published in a popular publication the trolls can’t wait to comment about how people with allergies don’t deserve equal rights or that it’s not a real disability. These things are harsh, but they are meaningless trash talk. Don’t let the trolls get to you! Instead I take it as a sign that the post had a significant enough readership that I wasn’t just preaching to the choir, and that it was thought provoking enough to garner commentary and ruffle some feathers.

If you liked this post, check out my video about A Week in My Life as a Freelance Creator