I Became a Serial Entrepreneur for My Daughters - Here's Why (and How)
Learn how Jessica escaped her corporate gig and launched her own business.
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I usually have a few standard responses whenever I’m asked how I balance raising a family and being a serial entrepreneur. I might jokingly brush it off as a “hot mess” or give a sage response about proper work-life balance. Every so often, I’ll provide a motivational quote about reaching my dreams and meeting my goals.
In a way, these are all true. It is hard work to achieve balance. And, sometimes it feels as if I’m teetering too far to one side or the other. But, for the longest time, I avoided the truth: I received plenty of help, and I was fortunate and privileged, more so than others. This made me feel selfish and a little fake.
But lately, I’ve come to a realization. My story is not one of overcoming extreme hardship, but it could still help others — especially working women — as they write their own success stories.
Whether they are looking to support a family and lock down a mortgage or simply want to prove themselves (to themselves and others), women entrepreneurs face similar obstacles. Just maybe my story can help someone else gain confidence – and a few practical tools – as they find their way.
When I started my professional career, I wanted to climb to the top. CEO, downtown view from my corner office, clout behind my name — that was my goal. I still remember the moment I changed my mind. And I hadn’t even considered starting a family yet.
After a week in the office, it was evident that politics and “playing the game” would determine my success, rather than my intellect or my skills. It would depend as much on how many hours I spent at the office and how I dressed, as much as it would on my talent and skills.
I probably would have succeeded, if I had followed that route – at least to an extent. I might have changed minds and revamped office culture for some. But I decided to follow my own path instead.
I dreaded being seen as “the martyr.”
Selfishly, I wanted to succeed for me, not others. Becoming a beacon for women’s advancement felt like too heavy a burden to carry on my already uphill path to success. Women still only earn 93 cents on the dollar, compared to men. Back then, it was even more.
I was privileged.
The fact of the matter is, part of the reason I became an entrepreneur is because I could. I was fortunate to have money in the bank and credit to lean on. I had a supportive family and a great mentor who brought me into his circle and championed my skills and abilities. Even today, privilege is a boon that many — especially women — don’t have.
The truth is that “pulling yourself up by your bootstraps” only makes sense if you have boots in the first place. And some are walking barefoot. Increasing the minimum wage could give everyone boots. Providing cheaper and more accessible healthcare and childcare could make it more accessible for anyone to pursue entrepreneurship.
Finally, I didn’t want to choose between a career and a family.
At the time, I didn’t know when or if I would be married or have children. But I wanted the choice. A decade later, after marriage and the birth of my first daughter, I knew I made the right decision. My family became just as important as my career. Too often, women are forced to choose to have a chance at success. Now, with two daughters, I know that I have set a good example for them.
Even with my considerable privilege, my path to success was not fun or easy all of the time. But every mistake I made was an education. Every misstep was a chance to learn a crucial new skill, trick, or tool to help me along my path. Every challenge I overcame gave me the confidence to do and be more. The lessons have been invaluable, and they are definitely worth sharing.
Work-life balance is not always 50/50
Sometimes family carries more weight, like when you’re nursing a sick child or supporting your partner’s dreams of going back to school. Alternately, when you’re starting a new business, launching a new product, or simply dealing with the unexpected, work tips the scale. And that’s ok. To be successful, you’ve got to be fluid.
Still, planning and preparation is key. I learned to manage expectations for my family and my clients by being upfront and honest about my availability. It took me a while, but I found a routine that allows me to separate work from home, giving each my undivided attention for part of my day. I also made a plan for emergencies for both my home and business, so everyone would know what to do if life threw us a curveball.
During moments of calm and abundance, I planned for the not-so-good times. I paid down my debt and built up my savings. I prioritized healthcare and retirement, and I am in the process of checking every box on my estate planning checklist to ensure that my family would be secure if anything were to happen to me. We’re all mortal, and life is full of surprises. I used an to ensure my family, our health, and my businesses would continue to thrive if I suddenly stopped.
There’s a grant for that
This is perhaps the most surprising and beneficial lesson I’ve learned. My initial ventures were successful, but I soon realized I needed more funds to reach the next level. I didn’t want to use my personal savings, and I wasn’t ready to take out a loan. Fortunately, my mentor connected me with a grant writer.
Since then, grants have become an integral aspect of my business. In addition to securing funds myself, I’ve introduced countless clients to the tremendous grant opportunities that exist to pay for my services. Winning grants propelled my businesses forward, and they are one of the few funding opportunities that are more accessible to disadvantaged business owners.
Grants are frequently targeted to demographic groups that are underrepresented in business. As a woman, I am eligible for certain grants for minorities. For example, the Amber Grant awards $10,000 to a different woman-owned business each month for start-up costs and continued growth. And at the end of the year, one of those women wins an additional $25,000.
Ego is the enemy
Forging your own path is rewarding, but you can’t do it alone. Some women might feel that asking for help diminishes their accomplishments, but I know that to be false.
Surround yourself with supporters that are eager to help you achieve your dreams. Find mentors in business, and create a network of like-minded allies who can help fill the gaps in your own talents. Find a number’s master to keep your books balanced. Keep a web designer on speed dial. Even if you have the talents, you don’t have to do everything.
The same is true for your personal life. Find friends that are happy to pick your kids up from karate practice if you’re in a late meeting and a partner who does their fair share around the house. Oh, and make time to nurture your relationships, your hobbies, and yourself.
While my life may not look like the traditional example of success, I couldn’t be happier living it. In the end, I guess I really did find a way to “have it all.”