Becoming Self-Employed: My 5 Biggest Learnings So Far


My oh my, this has been a long awaited topic on my list to cover. I get questions about self-employment and blogging ALL the time, and I truly love helping out to the best of my ability. I'm in this with the rest of you - If what I've learned can help a few of you take the next steps towards pursuing your dreams, then count me in!

So, here is what I've learned since becoming fully self-employed:

Quitting your job is not the end of the world.

I've left two different jobs without anything lined up - The first time was to travel to Nicaragua for my yoga teacher training. The second time was to work for myself... and here I am. No one should ever fear leaving a job or losing a job. Both happen, and it's more than okay. It might seem scary, but it's really not that big of a deal. You can find a new job if self-employment isn't working out for you.

Expect to work 10x harder.

Yes, you should always give 110% no matter what you do. But let's be real - if you're on your own freelancing, consulting, blogging or all of the above, you're going to hustle a hell of a lot harder, because you're keeping yourself afloat each and every day.

When you work a 9-5 salary job, it's more stable, and you start to get comfortable in your day-to-day. If you decide to leave a steady income and go rogue, you're going to be more of a workaholic than you already are. But guess what - you're going to LOVE it, because you are doing what you are passionate about, and you are working with clients/brands/partners that you choose to work with because you align with them. No one is forcing  you to do anything you don't want to do.

Productivity is more important than ever before. Let technology help you.

If you're a master procrastinator, you'll figure out pretty quickly that waiting until the last minute will only cause you unnecessary stress. Get comfortable using the Google suite (drive, docs, sheets, and calendar), Dropbox, and apps like Trello  and Toggl. I use Google Calendar for all of my meetings (even personal), and I use it to block out time for my daily to-do lists (Example: 9am-10am - Write Blog Post on Self-Employment).

work for yourself - self-employment tips
work for yourself - self-employment tips

Photo by Victoria Jane Photography

You'll become a master at managing your finances.

YES, you will! This is the biggest concern I get from most of you. Well, let's start with a Google excel sheet. I track, categorize, and calculate all of my income. When you're a freelancer, you have money coming in from every which way, and especially for bloggers there are a lot of one-off jobs and W-9's galore. Write it down, keep your receipts, and download Quickbooks Self-Employed (here).

3 More Important Finance Tips:

  • Apply for an Employer Identification Number (EIN #) - This way you don't have to give out your social security number to a bajillion random companies. It takes 10 minutes (here's a link).
  • Get a separate biz account - This is going to help you immensely when it's tax time. You must file quarterly taxes if you're self-employed, so ALWAYS put money aside for taxes. Also, BLOGGERS: you have to pay taxes on all of the gifts you receive (if you post about it). So, even if you're not getting paid, you still need to file it as income. Consider this when you accept free products.
  • Hire an accountant - This is my first year filing as self-employed, and I don't want to mess that shiz up. So, I hired an accountant to teach me his ways. Hopefully after one successful year of working together, I can file my own taxes. Happy to recommend him to you if you live in NYC.

*** If you want more insight on specific finance questions and general organization tips on tracking systems/templates I use, I'm offering one-on-one sessions (see at the bottom of this post).

You have the ability to make more $$$ than in your 9-5.

Well, not at first. There's a lot of adjusting in the beginning, but you will find your sweet spot. If you're a consultant or a freelancer, you can work as little or as much as you decide. Some months you make a lot, some months you make a little.

When you have a salary, you know how much you're getting every pay cycle - that number doesn't change, which can be VERY frustrating if you work like a dog and feel underpaid and under-appreciated. The good thing about self-employment is that you set your rates. You decide what your time is worth based on the scope of the project, and you CHOOSE to either take on a project or not.

It's a simple recipe: the more you take on, the more money you'll make. You may be working all the time, but if you love what you're doing it will be rewarding and enjoyable. And if not, then drop the project.


Photo via MindBodyGreen

- Schedule a Strategy Session with Me -

Have more specific questions about blogging, freelancing, starting your own biz, or you just want to pick my brain? I am now officially offering one-on-one sessions in one-hour time slots! Email me for more information regarding rates.

P.S. I'm now offering this, because it has been widely requested. I've been under-the-radar Skyping with several of you, so figured it's time to make it official. =)

P.S.S. If you're a Freelancing Female... join this very insightful Facebook group of boss ladies helping other boss ladies!


becoming self employed - 5 lessons learned
becoming self employed - 5 lessons learned

That's all for now - speak soon my fellow entrepreneurs!