The person I aspired to be like quit the dream I’ve been chasing. Instead of questioning my own intentions, I doubled down my determination.

Less than six months into our arrangement she quit freelancing.

She accepted a full time position at an agency.

She confirmed that having the flexibility for making your own schedule and getting paid well when you do work is worth the effort of being your own boss. I’ve worked in the corporate and non-profit world for 14 years.

Honestly, I don’t want to dress up to go to work anymore. I want the freedom of running errands during “normal business hours.” I long for the independence to get up in the morning, work a few hours, go for a horseback ride or run, come back and work until the project is complete. And my Labrador Retriever Molly will probably be the best office mate I will ever have (with the exception is my current one who is awesome).

The inconsistency of cash flow can understandably create extreme anxiety. Family circumstances and corporate downsizing are sometimes the reason freelancers hang out their shingle. I’ve been extremely blessed that neither of those situations have happened to me. Instead, I’ve steadily built a savings account to bridge that gap when I finally get there.

Early in my corporate career a boss suggested having three years’ worth of salary in the bank before starting a company. The natural course of my career advancement has pushed that ceiling higher and higher.

There is always the reality that having a large nest egg can create paralysis (this has been my problem). Working with a financial planner has helped me work through that. Bottom line is that having some savings can make it easier to ride out the ebb and flow of freelancing.

Not long after my mentor quit, I followed up on the advice from the owner of a local association management agency. She gave me the names of three successful freelance writers in my local area. I hit the jackpot. The first one I called graciously shared her expertise, going rates in the industry, the strength of the local freelance economy and much more. More importantly, she’s holding me accountable to creating and sticking to a timeline.

The moral of the story: find someone who will be honest about the ups and downs, who can encourage you and hold you accountable. Want to chat? Connect with me at