Ask Joblogues: Should You Quit Your Job to Freelance or Begin a Start Up?


During our advice segment on Episode 13, Krys asks us to discuss trading in a full-time corporate job for freelance work and entrepreneurship. Sakita Holley, CEO of New York-based PR firm, House of Success, offers up her advice for anyone considering taking the leap. Before you quit your job, think through these key considerations:

Identify what you want.

What are you trying to get out of quitting your job? What are your underlying motivations? More time? Freedom? Flexibility? Money? Starting by identifying your root motivations will help you lay out multiple paths for achieving your desired outcomes. For instance, you can always freelance while you’re working full-time to make more money, but might need to give up a full-time job if you’re in a field where clients demand your undivided attention and time.

Create a game plan.

After you’ve figured out what you want and why, set a timeframe for accomplishing that goal. Before quitting her full-time job in financial services, Sakita set a quit date 6 months out and itemized all of her recurring expenses. She knew how much money she’d need to save and how much income she’d need to generate as a business owner to take care of her bills. Doing this helped her to realize that she had no choice but to make it work.

Recognize the potential pitfalls.

A common misconception about leaving a full-time job and freelancing or working for yourself is that you’ll be freed of mundane and unfulfilling business tasks. False. If anything, the burden of juggling multiple priorities increases when you work for yourself. The onus will now completely be on you to figure things out without the support of a larger organization, so realistically ask yourself if you’re committed enough to manage everything from invoices and accounting to getting new clients and business development and on your own.

Passion isn’t enough.

Ultimately, your decision will boil down to deciding the type of life you want to live. Working for yourself is a constant hustle and will take up all of your time. If that doesn’t motivate you and you don’t shine in those instances, it may not be for you. We hear “pursue your passion” so often, but the reality is that passion alone isn’t enough to sustain a business.

Tune in to Episode 13 to hear more of this conversation. Remember, you can always submit your own career and life questions to us by visiting


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About Author

Joblogues is an interactive resource and podcast designed to inspire and empower young professionals to reach their full career potential through storytelling and shared experience.