At the beginning of the summer, I told you all about the benefits of a part-time job (and how much I loved mine). The part-time job is a wonderful stepping stone into self-employment, so I hope those of you who are contemplating a transition will go back and read that post. But what if a part-time job doesn’t suit your needs (anymore)? How do you know when it’s time to take the plunge to working only for yourself?

That was one of the (many) lessons I learned this summer.

Two things happened simultaneously. The first was that I started taking on more of my own clients. The second was that my desire to work 80-hours a week/all weekend long was clearly on summer vacation. Obviously, I should have been more realistic about my availability, but I was being flooded by inquiries from amazing people — my RIGHT people — and couldn’t say no. The harder I pushed myself, the more blocked I felt. By mid-July, I was overbooked, overwhelmed, over-promising and under-delivering. (Bad, bad, bad.)

It was really disheartening to realize that I wasn’t giving my best to either thing anymore. I’m not a person who brushes off her failures or makes excuses for her mistakes. If I had to pick a single thing that I am proud of, it’s my work ethic. Watching that suffer was so, so hard.

I sat with this struggle for a bit. I did all of the things you’re supposed to do — I talked to friends. I talked to my therapist. I made lists. I did yoga. There was no easy answer. It was time to leave my part-time job and focus on my business.

I gave four week’s notice, which you’d think was plenty of time to prepare — but oh how I cried when it was time to say goodbye. Being a part of Sarah‘s team had been a dream come true for me — but it was time to make space for growth (for both Sarah’s business and my own).

How do you know it’s time?

Why was I so sure that leaving was the right thing to do? Here are some signs that you’re ready to abandon your day job and focus on your thing:

You’ve laid the foundation for consistent cash flow. You want to be fairly certain that the money is going to keep on comin’. This probably goes without saying. There are instances, of course, where you won’t really be able to see your true income potential until you’re able to totally devote yourself to your business, but be realistic. If you currently sell one painting a month or teach one yoga class a week, just freeing up time isn’t going to make it rain money. If you need your business to sustain you from day one, make sure you’ve put the horse in front of the cart. (Take on commissions, book classes, schedule consultations, whatever it is you need to do.) When I gave my notice, I had a waiting list two months long. Furthermore, only 25% of my income was coming from my part-time job even though I was giving it 50% of my time/energy/focus.

You’ve established quality client relationships. When I say ‘quality client’, I’m not referring your sister-in-law, because she wants your work for free. I’m not talking about your hairdresser, because she only pays in trade. I’m not even talking about the aloof executive you met at that networking thing — because working for her might bring you a paycheck, but it doesn’t bring you alive. ‘Quality clients’ are the people you enjoy working with, and who are grateful to be working with you. They’re the people who eventually toe the line between client and friend, and who tell everyone they know to give you buckets of money. Find these people.

You have a wide and varied support system. You should have someone you can call for advice when you bump into a sticky client situation, and someone whose shoulder you can cry on when things are bumpy and difficult. You should have someone in your corner who has been there and is better for it, and someone who believes in you even when you totally screw up. If you’re surrounded by naysayers, cultivate a garden of cheerleaders. Shake off the bad-attitude fleas and find better friends. (And don’t be afraid to say ‘I told you so.’)

You have a rainy day account. In fact, you should be prepared for at least a month of rainy days. (Some people say a year, but come on. Believe in yourself. It’s okay to be a little adventurous.) There are ebbs and flows in any business. You might make $6,000 one month and $600 the next. Be prepared. I’m not a big proponent of backup plans, but make sure you can survive at least a month without any income at all. (You’ll probably never get to that point, but you’ll do better work without the fear of homelessness looming nearby.)

You’ve purchased health insurance, disability insurance, and a helmet. Just kidding about the helmet. But don’t be reckless – especially if you’re already sick. Make sure you won’t be financially ruined but unforeseen circumstances. If you’re already sick, don’t consider medical treatment optional. I’m telling you this because I made this mistake the first time around. I was in therapy and on medication for depression, and quit both cold turkey when I left my last job. The year that followed would have been so much easier if I’d come up with a healthcare plan and considered that expense a priority.

And, go!

If all of these things are in place, I think you’re ready. Just in case you’re unconvinced, I’ll be talking with other creatives who took the plunge and profiling them here this fall.

If you’ve already taken the plunge, how did YOU know it was time?

PS. As you might know, leaving my job with Sarah J. Bray wasn’t goodbye for good. We’ve teamed up in a new way, to bring you Litesites as a LeahCreates service. Squee! Go take a look.