Liberty Road

written by Stacey Lindsay

Leigh Oshirak knows how to grow a brand. With over three decades of experience in marketing and digital content, the author and businesswoman has bolstered household-name giants, including Birkenstock, West Elm, and Pottery Barn. She later co-founded a consultancy firm with two other women where they worked with female-founded and run businesses. “It was such a joy to work where you were valued and work where there was an unspoken language,” she says of her consulting work.

Still, Leigh admits: Consulting has its pain points. From scope creep to toxic clients, some elements can gravely interfere with the joy of being your boss. Leigh calls such pains “watch-outs” and is keen to share them with other women in consulting. Her insight is invaluable, especially given a continued swell of women leaving their corporate jobs.

Whether you’re daydreaming about becoming your own boss or looking to uplevel your consulting work, Leigh makes a compelling case: Boundaries and knowing your worth are keys to loving what you do and doing it successfully.

Leigh Oshirak’s 6 “Watch-Outs” for Being Your Own Boss

#1: Set Boundaries

When Leigh left corporate America, she made hard and fast rules. She vowed she wouldn’t work with toxic people or when she saw red flags. “When clients were coming to us for proposals and projects [...] I was very in tune to: red flag, red flag, red flag. I said no more than yes.”

#2: Consider the “Fit and Feel”

You often don’t get to choose who you work with in corporate America. But when you’re consulting, you have agency—so employ it, suggests Leigh. “In this capacity, I made a decision that fit and feel was equally important as all of it,” she adds. In taking on clients, she suggests considering the following: How would you feel when working in the trenches with this person? How will you interact together? How do I feel about this relationship?

#3: Honor Your Time and Energy

Think about the minimum time you need to deliver for a client successfully. This may mean creating a six-month contract, or this may mean a year contract. Also, track your time with software such as Harvest. This offers clear awareness about the time and energy you put forth so you can charge an appropriate fee. “So when you bid a project you know, I bid that project for 100 hours but it really took me 200. Lesson learned.”

#4: Take Structure Seriously

The idea of working for oneself too often elicits the thought, I can let the babysitter go. I can do it all. “You still need to have structure in your life and to create structure,” says Leigh.

#5: Opt for a 60-Day Out

Every contract must state a termination clause—a provision defining the circumstances under which the work agreement can be terminated. Leigh says always to give yourself a 60-day notice contract rather than a 30-day. “That allows you enough time to onboard a new client when someone gives notice.”

#6: Consult with a Partner

There is freedom and joy to owning your own business and owning your time. But a two-week vacation may not be an option when you have a weekly call with a client on a monthly retainer. The solution? Go into consulting with a business partner. “You need someone to back you up,” says Leigh.

These tips were pulled from our original chat with Leigh and edited and condensed for clarity. To listen to the full conversation, head over to the Liberty Road Podcast here.