9 Lessons From A Year Of Self-Employment


This past September marked my first official year where I was steadily self-employed  -  pop champagne! I have done this little song and dance of entrepreneurship since 2011. I would go out on my own - freak out, get a "REAL job" - be distracted and absorbed in my new line of duty- get hopelessly depressed (feeling like I coped out) - jump back in to the self-employment arena feeling undefeatable - then crash and burn - repeat.

It’s was exhausting but I have finally got it to stick. Here are just a few of my learning’s this last year. 

Choose your sh*t sandwich

Because we all have to do it. When I read this on this blog I found on Facebook ions ago, It came with this SAGE advice: "Everything involves sacrifice. Everything includes some sort of cost. Nothing is pleasurable or uplifting all of the time. So the question becomes: what struggle or sacrifice are you willing to tolerate?"The shit sandwich is just inevitable and you have to choose what is worth it. Personally, I HATE that I have to do accounting and taxes, and I HATE that there is no guaranteed income every two weeks (who wouldn't) because it means I can’t be lazy. It was SO much easier arriving somewhere at 8:00 am and leaving by 4:00 pm and getting a nice little cash flow every two weeks. Trust me, I would rather curl up on a couch with some tea, watch a movie and let the clients come rolling in on their own, but it won’t happen. Mundane everyday jobs are kooshy like that, but I would rather hustle than play small and feel safe now. The good far outweighs the bad. This leads me to…

You're going to have really bad days

Like really bad, but I won’t feel sorry for you (I know, ouch) because it comes with the territory and it's essential in your learning to stand on your own. You are going to want to cry out of frustration, binge eat ice-cream and chocolate, you are going to feel vulnerable, afraid, unworthy, overwhelmed with everything you have to do, hate every deadline that creeps up on you, get annoyed with people who want free stuff all of the time, feel like crap from the mistakes you have made, etc. They are going to happen but I can promise you that you will be so much stronger and smarter afterwards and these days really make the amazing days that much better.

Lean on others

With the bad days you are going to need a strong support system behind you. Whether it is family, your partner, your best friend and other like-minded business people going through the same ups and downs. You need to lean and share what you are going through in order to work through it or you might spontaneously combust and start applying for jobs on indeed. (Been there, done that, got the cover letters to prove it.) 

Stop being a drama queen

This one makes me laugh because this whole year I have realized how much of a drama queen I could be, just give me a golden globe already. What I mean by this is that you are going to blow things totally out of proportion when it comes to your comfort zone. That thing you really want is actually not that hard, you are just making it harder in  your own mind, belieeeveee me. If it freaks you out, there is a good chance you need to do it and once its over you will realize how ridiculous you were dreading it for so many years.

Do what you love, but ask yourself WHY?

 I think this is my biggest pet peeve with all the business coaching out there, they are always brandishing the slogan “Do What You Love” but doing what you love is maybe a third of it and I think that's why people get lost. I love a lot of things and I am good at a lot of things (design, writing, illustrating, crafty things, etc) but I don’t want to go in to business with all of them. You have to choose one that you are really naturally good at (you can usually tell what it is because people will ask you to do it a lot or ask for guidance in that field) and then ask yourself WHY you are going to pursue it. There needs to be a bigger reason at play. You need your very own mission statement.  “Because I am good at it” won’t last. It has to be something you want to share with other people because you know it will change their lives, you need THAT kind of passion! You will get bored or you will hate doing it for other people unless you are intending something bigger than just merely doing it. You feel me? Example: I love web design, but I don’t really want to do web design for other people. It would totally kill the pleasure of it for me because I have no bigger plans other than... I like making pretty things. I could write a whole blog post about this, maybe I will in the future, but for now go buy this book: Start With Why by Simon Sinek.

Heck Yes.

I love Danielle La Porte. This one is the key component I use every single day for when I take on a project or client. If it isn't a “heck yes, I am so excited about this,” than I will not do it. This helps you protect what you love and it will protect you from spinning the wheels on doing too much. Please keep in mind there is a difference between FEAR and DISINTEREST when it comes to this gem. FEAR is a good thing to work towards, DISINTEREST is a silent killer of joy. I killed my love for photography a few years ago when I did a project that took me 8 months to complete taking photos of something I actually didn't really like. I stopped taking photos for 2 years after that and the spark was gone, all for a paycheck that wasn't worth squandering my love for photography. Choose wisely obi-one, choose wisely.

You don't have to wear all of the hats

It isn't a secret, entrepreneurs wear a lot of different hats in business; president, creative director, marketing manager, director of sales, social media strategist, administrator, janitor, web designer, photographer, design specialist, accountant, techy, etc.  The thing is… you don’t have to do it all and I don’t recommend on doing it all unless you really really want to. The more hats you wear, the likelihood the longer your business will take to lift off and flourish because there is only one of you instead of like…five. Invest in people you want to work with and who will make you grow. If you don’t know how to use Photoshop and illustrator to make a logo, please please hire someone who is trying to take off like you and collaborate! If you have no idea how to build a social media platform or brand, then consult with someone or take workshops. It’s true what they say, you have to spend money to make money and going local is pretty special because you will meet new people in your area who are doing big things like yourself. Yay, new friends!

Screw your strengths

Focus on your weaknesses, for now. Don’t waste your energy on focusing only on the things you are already great at, even though it makes you feel so gosh darn good. Spend time on choosing things that you have no idea how to do, take on personal projects, set goals, and track your income, save receipts no matter how much you hate doing it. 


Escape your house

Or you will go CRAZY! Most of us work out of our homes which come with its own distractions and frustrations of being home owners. Get out as much as you can, meet other people in your field, work from a coffee shop, and go for walks when you feel like you hit a dead end. Don't ignore the dog, you will feel guilty for it later and please ignore the laundry, you're just procrastinating. 

Thank you to my incredibly handsome partner in crime, Landon, for being a constant source of inspiration (you are so talented,) support, and handled my crying, self-doubt, and anger towards your clothing shopping sprees (because I couldn't do it too hah). You handled every moment with grace, patience, and sincere love. You have put up with a lot this past year and I love you so much, you really do make me a better person and I aspire to be as patient and giving as you. 

Thank you to my bestie Samantha for being my co-entrepreneur for listening to every set back and moments of pure fear you helped me step away from the ledge and made me realize that somedays it sucks but we still get to do whatever we want (like go to indigo and drink coffee) most of the time and that's pretty awesome. haha!

Thank you Ella, my pup, for bringing me down to earth and being a constant source of love, joy, and hilarity. You are so goofy and you remind me to stop taking life so seriously. 

Also thank you to my mother who has been an inspiration to me since she took the self-employment plunge even as a single income mother with two children. You were fearless when you could have been safe. That really set me on the path that I am today.