“We should all start to live before we get too old. Fear is stupid. So are regrets.” —Marilyn Monroe

Working for myself was always on my bucket list but I never felt prepared enough. How would I know when the time was right? What could I do to make make the transition easier? Week after week, I held onto my stable, well-paying job, afraid of making a wrong move.

After all, from the outside, it looked like I had it made. I constantly asked myself why it was so important that I set out on my own. I had a great career with as part of a brand team working with huge, recognizable companies and I was petrified to leave it all behind. Part of my fear stemmed from my background. I’d grown up in a family where my parents always had traditional, 9 to 5 jobs. I valued stability and set routines. Stepping into a life of freelancing meant that I was signing up for the great unknown.

I saw other people freelancing full time and they seemed to be doing okay but what if I wasn’t as savvy at finding new clients as them? What if I completely failed at my dream? The “what if’s” never slowed down.

Then, one day my friend invited me to a small business class. One of the activities centered around facing our fears. We were each told to take out a sheet of paper and spend a few minutes writing out our worst case scenarios.

Most of mine centered around not having enough client work. My worst case scenario was asking for my old job back or going out and finding a stable, corporate job for awhile. I stared down at the list and almost laughed out loud. My worst case scenarios weren’t bad at all. What was I waiting for?

Next, we were instructed to place that list of fears in a Ziploc bag, zip it closed, take it home and put it on a shelf.

Done.

My fears were now out of sight and out of mind.

Once I had that reality check, I realized how much time I’d wasted worrying about tiny things that in the grand scheme of life really weren’t a big deal.

Less than 6 months later, I gave my notice. That was over 2 years ago.

Of course, there have been ups and downs but I’ve been fine. My business has nearly doubled over the last year and now I have the freedom to set my own schedule. I definitely work harder but I also see the direct payoff of satisfied clients and new opportunities. Was it worth giving up my stable routine? Yes, absolutely.

Here are 5 tips to prepare for the transition to freelancing:

1. Set up a designated workspace now.

Even if you’re 6 months out from quitting your full time job, having a designated workspace will help you get more comfortable with the reality of your new path. It’s okay if your desk is in the corner of your bedroom. Set a schedule, whether it’s mornings, nights or weekends and get to work. How does it feel? What can you do to make your spot feel more official? Buy plants, artwork and matching office supplies to help you get in the zone. Need some inspiration? Here’s my old home office!

2. Save a minimum of 6 months of expenses.

There’s nothing worse than feeling desperation set in because you didn’t save enough money. A serious safety net will make it possible to focus on putting out your best work without the imminent fear of starving or getting evicted. Save, save, save! And then, save some more. Money isn’t everything but it does give you the luxury of saying no to opportunities you know aren’t a good fit.

3. Have your portfolio and website ready to go.

These both take a lot of time to get together so you may have to set some goals long before you give your notice. If you don’t have a budget for a custom web design, that’s okay. Work with what you have and you can always upgrade later. My first pro portfolio was on Cargo Collective and it worked great. Squarespace is another option. You never know who is going to stumble across your work. Both Forever 21 and Virgin Records hired me based on work I’d posted online.

4. Network like it’s your full-time job.

The easiest path to freelance success is to build up your network of creative peers and clients. To get started, do as much free marketing as you can on social media — my favorite platforms to share work on are Instagram, Dribbble, Pinterest and Twitter. I also still find blogging to be really valuable because it allows me to go deeper and share more of the process and story behind each project. Once you’re making some decent money, invest in in-person events. There are dozens to choose from but I’ve had the best results with Designer Vaca. Finding the right mix of networking opportunities takes some trial and error but the point is that you’re making an effort to connect.

5. Set up contract opportunities.

Freelancing doesn’t feel as intimidating when you have a backup plan. When I first started freelancing years ago, any time I had a slow period, I reached out to placement agencies like Aquent and 24 Seven. It’s in their best interest to place you because they earn a commission. They want you to be happy so you stay put! Between the two, I always had a steady stream of work. While I only work with my own clients these days, I’m still great friends with my agent, Dan and know he’s just a call away.

I know firsthand how scary it can be stepping out on your own. Being your own boss is no joke! But through my own journey, I’ve also realized that you have two choices in life: you can either keep holding yourself back or you can ask yourself what your worst case scenario is.

Is it really that bad?

If it isn’t, you know what you need to do.

Your turn: Are you thinking about freelancing full-time? What scares you the most?

For even more Creative Chronicles, please click here.
Photo: Shell De Mar.