Everyone has a unique first step into their entrepreneurial or freelance adventure. Personally, while I always knew I wasn’t cut out for the 9-5 office job, I never believed I’d actually make the leap and start my own business.

If anything, I had a lot of… mindset blocks from my childhood that really colored my perspective on a freelance lifestyle. I also had a pretty bad self-esteem issue that made the idea of putting myself “out there” literally left me with knots in my chest.

But I guess that’s the funny thing about life…

Everything (including yourself) can change in an instant.

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How I became a freelance mom

Quite frankly, it was wholly unexpected.

When I got pregnant, I’d been working for a company for 6 years (my 6 year anniversary was that December). While I was very unhappy at my job (I loved my coworkers to death, I just wasn’t doing fulfilling work and had no idea how to change that), I never intended on being a stay-at-home mom.

Nothing wrong with it, I just really love working, so it wasn’t for me.

But after finding out that my j.o.b was NOT going to be flexible about me needing a 2-day-per-week remote working schedule in order to not have to put Jake (my son) in daycare, my reality turned into a tornado.

Again, nothing wrong with daycare, it just wasn’t the most financially or emotionally equitable decision for my family situation.

So I went into a pretty tough headspace. I felt defeated and trapped. I even felt betrayed.

When one door closes

I quickly realized that bathing in those negative feelings was NOT going to solve my problem, and if it’s one thing my anxiety is really good at… it’s compelling me to try and resolve “problems” as quickly as possible.

But I really didn’t know what to do until, one day at random, one of my dearest coworker-friend’s made a suggestion (or rather, emphatically encouraged me and lovingly but firmly verbally drop-kicked me out of my comfort zone… you know who you are.)

My friend said to me: “Why don’t your try going on UpWork and get copywriting jobs? You’re good at writing

Now, at this point, I’d only heard of the term: copyright, so I initially thought she suggested I do some form of legal writing, and I was like “HELL NO, there’s no way I’ll be able to do that!

But she told me to do some research, so I did… and discovered a whole new world.

$5

After some research and just enough desperation to outweigh my poor self-esteem and fear of failure, I decided to try my hand at scoring a writing gig. If, for no other reason, than to prove to myself that I was shit and could abandon all hope of ever having a career in writing (which was a lifelong dream)

I created an UpWorks account (this is not me saying one way or the other whether UpWork is good or bad, this was just how I started), and sent a proposal for a 1500 word blog post for $5.

But you know what… that was the most important and validating $5 I ever made. Not only did I win the proposal, but I spent hours crafting that blog, submitted it, and received super positive feedback… INCLUDING a testimonial!

I couldn’t believe it… but that was my first step into a whole new world I never knew I could be a part of. I realized how much I loved writing copy (I always loved creative writing), and the idea that I COULD make something out of it was eye-opening.

So I kept applying to little jobs on UpWork, won proposals, and even scored a long-term client from them!

Friends and Family

I got my first website copy projects from friends and family, and each one was fun, stressful, and massively educational. I learned so much, and it was wonderful to see that my work made others happy- especially others who were running their own businesses.

So for the last 3 months of my pregnancy, I hauled ass on client work, submitting UpWork proposals, and building a website full of portfolio pieces that I mostly made up on the fly.

New Mom and New Freelance Business Cocktail

After my son was born, it was only a couple of weeks before I started finding writing work again. Quite frankly, I loved it, and it was a “me thing”, which is super important during postpartum when you’re feeling out of place and like a stranger in your own body.

One day I looked at my husband, and I said:

I’m setting a deadline for myself. if I can make a consistent income by the time my Maternity Leave ends, I’ll become a full-fledged copywriter. If I can’t, then I’ll figure out how to get another day job.

My husband was supportive either way, but this was a REALLY important goal for me because:

  • It would really show me if building my own writing career from scratch was possible
  • I’d have the ability to RUN a writing business WHILE taking care of a baby full-time
  • And it would mean I’d never have to shove myself into boxes I didn’t fit in again

So I used the rest of my maternity leave to learn how to be a mom, and learn how to be a freelance copywriter.

And when my countdown hit 0, I had found 3 fairly-stable retainer clients, as well as one-off side-projects. I’d done it. I’d met my goal, and even if I wasn’t making a lot of money… I knew I COULD.

My Freelancing Life

From there I continued to revise and rejuvenate my website, work on copy projects, network, and make wonderful connections.

It’s been an incredible journey doing something I NEVER imagined myself doing, but I am SO GRATEFUL. And I know that I have a lot of privilege that made this leap much more feasible (and I’ll never forget that).

I love what I do, and that’s not something I ever thought I’d be able to say.

I’m so grateful I can show my son that you CAN build a life and business that fulfills you, and you can do so in a responsible way.

I leave you with this

All I ask is that you never forget you have incredible skills and passion that CAN build something. It can be so easy to think “we’re not good enough”, but I promise you are. Nurture what makes you feel whole, and believe in yourself. You don’t have to fit into someone else’s box to make a living… and you deserve a happy life that aligns with your goals.

If you feel like a fish out of water… then many you ARE.

Maybe you’re a fish trying to climb a tree, instead of letting go of your fear and falling back into the ocean where you can swim freely and be your most true and beautiful self. (Talking about all these fish reminds me of the Rainbow Fish, anyone else remembers that book?)

While I may not be the most “woo woo” person, as they say… I do believe in listening to your gut, moving with intention, and I refuse to believe that trying to follow your dreams is selfish, unrealistic, or immature.

It isn’t.

You deserve to feel happy and fulfilled, and I just want you to know that I believe in you, and that I’m rooting for you.

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