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To Be (A Momtrepreneur) or Not to Be + 7 Tips If the Answer is Yes

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When we found out I was pregnant, I could barely contain myself. I’ve never been good at keeping secrets. Weeks later (12 to be exact), I was ready to share my news. In the two years I had been at my job, I’d grown close to my boss. She was supportive, encouraging and provided a level of mentorship I had never experienced. Surely she’d be over the moon that I was expecting. After the hugs and the “I had a feeling!” immediately came the “You’re coming back, right? RIGHT?”

I’m a typical Type A personality: overachiever, highly conscientious and focused on being successful. Just a few weeks prior, I was selected as a “Forty Under 40®” award recipient by the Association Forum of Chicagoland. My boss was giving me free range to run our communications department. She reminded me often that I was one of her key executives and on the path to becoming a director in the coming year.

When my maternity leave came around, I was still trying to convince myself that I’d come back. After all, my boss said it was the right place for me to be. The thought of staying home with our daughter crossed my mind a few times a lot. But, my career was taking off. I loved my job and the people I worked with. I didn’t love commuting for three hours every day. When I lived in the city, it was a 20-minute train ride. When we became suburbanites (just three months before getting pregnant), that all changed.

A few weeks into my leave, all I could think about was work/life balance. I spent hours stressing about my options during late night feedings or while Ellie was napping on my chest. Special moments were starting to be clouded with uncertainty. I could…

  • Return to work full-time at my current job and rely on daycare from 6 a.m. – 6 p.m. Working remote was not an option (neither was a reduced schedule).
  • Return to work part-time (something new and closer to home) and rely on daycare a few days a week.
  • Become a stay at home mom.
  • Become a work at home mom… who owns a business.

I was obsessing over what to do. How could I go from spending every moment with our daughter to being away from her for 12 hours at a time? Would I even feel fulfilled if I wasn’t writing/problem solving/mentoring? Could we afford living on less income?

A few weeks before my scheduled return, I called my boss. I was nervous, mostly because I didn’t have a plan. I always had a plan. I didn’t want to disappoint her, and I also didn’t want to let my family down. Then it happened. I told her I couldn’t come back full time. It just burst out of me. I immediately felt relieved.

I wanted the best of both worlds: to be home with my daughter and to keep my career on track. I returned to work to tie things up and create a transition plan. Three months after becoming a mom, my gig as director of marketing and communications for a 20,000 member non-profit was up. (And yes, I got that promotion.)


August marks one year since I left my job and launched Cheryl Wilson Marketing. My daughter is now 15 months old. I’m proud that I survived the craziness of having a newborn (now toddler) while navigating running a business! We’ve spent spring days at the zoo and summer afternoons at the splash pad. At the end of her day, I hunker down and dive into editing, copywriting, social media or strategy development.

I understand why I was so stressed about making this decision. Luckily, it’s been the right choice for us. I’ve been present for Ellie while creating and maintaining happy client relationships. I’m not saying that it’s easy…at all.

Let’s be real. It’s a lot of work to clean house, do laundry, prepare meals, spend quality time with children, be a good wife and run a business. There will be moments when you don’t know how you’ll get it all done. But, with some patience (and a supportive partner), you will.

If you’re ready to become a work from home mom, here are some tips I can share as someone who has been through the transition.

  • Trust your instincts. Don’t try to please others or make decisions you’re not comfortable with. If your gut says you’re ready, you are.
  • Network early and often. I reached out during my maternity leave to ask people if they needed marketing or communications support. When I mentioned I may be available to freelance a few hours a week, they were all over it. That helped me make my decision to go solo. To date, all of my clients are past employers, friends of friends or referrals. Not having to cold call has made things less stressful, but I know I’ve been lucky.
  • Develop your personal brand. Before I quit my job, I laid the groundwork for my business. I had a friend design my logo. I ordered $15 business cards off of vistaprint.com. I built a free website using WordPress and then secured my domain name for $29/year. I got myself up and running in less than a month. Put the effort in upfront to have all of your bases covered. If you want clients to take you seriously, you’ll need to present a professional image. Be prepared to share the services you offer, your pricing structure (hourly, project or flat fee), work samples and testimonials.
  • Only take on what you can manage. At first, I didn’t know what that magic number was. Once we got into a routine, I knew I could handle 10-15 hours of consulting a week – mostly working at night and when E napped. Only now am I willing to take on 15-20.
  • Have structure. I preach to my clients the importance of work plans with milestones and deadlines. Ironically, I’m more lenient when it comes to my own business. Even if you only have a few hours to devote to your clients a day, know when those hours will be and how you will spend them. Keep yourself organized and set boundaries. It will help you focus on your clients when you need to.
  • Ask for help. I’ve got a supportive husband who does his share of housework and helping with Ellie. It makes it easier for me to sneak away to do work when I can count on him. If I need to schedule a call or work on something while she’s awake and he’s at work, I have Ellie’s grandpa visit. I also started to have our teenage neighbor over for two hours a day, twice a week, to entertain Ellie while I’m working. I wish I did that sooner!
  • Avoid burn out. Some weeks will be busier than others. Sometimes you’ll really, really want to lay around and watch the Real Housewives of New York when you should be working, writing a proposal or sending an invoice. Being a mom is a lot of work. Being a mom with her own business is another story. Take “me time” to recharge, otherwise you’ll be raising the white flag in no time.

Still, some of the best advice I’ve received is that “You’ll never wish you spent more time at work and less time at home with your kids.”

At the end of the day, remember what your goals are. If it’s to take control of your work/life balance, becoming a boss mom makes sense. In 15 years, what will you look back on with pride? We’ll either love the time we had with our families or wish we would have taken more. 

What is your next big goal? Let us know in the comments below

Get to know Cheryl: 

CW_HeadshotCheryl Wilson is a Chicago-based marketing communications professional with more than 10 years experience working for associations and small businesses. She specializes in writing and editing copy for websites, collateral, e-mail, newsletters, magazines, blogs and social media. Cheryl has a track record of growing membership and event attendance, and helping new managers and junior staff succeed. She helps teams deconstruct an event, process or project into easier-to-accomplish tactics and deliverables. She enjoys dancing to Sesame Street’s “Number of the Day” with her daughter Ellie and having a good craft beer with her husband every now and then.

Visit Cheryl’s website at www.CherylWilsonMarketing.com or on Facebook at www.Facebook.com/CherylWilsonMarketing. Reach her via e-mail at CherylWilsonMarketing@gmail.com.

Dana Malstaff

Dana Malstaff

Dana Malstaff is the Founder of Boss Mom and creator Nurture to Convert.
She is a mother, author, speaker, messaging strategist, podcaster, blind spot reducer, and movement maker. She believes that too many brilliant moms are struggling to figure out how to grow their business while balancing all that is required to be a good mom, partner, and woman. So many moms are trying to grow their business using trends that feel inauthentic and aren't realistic for their inconsistent schedules. She has helped thousands of women become known for their brain and not their dance moves

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