3 Life Stages of Entrepreneurship - and Why We All Need Each Other

3 Entrepreneurs all in different life stages. My son Calvin, Me and my long-time subconsultant and friend Amy

​With my son busy building his video production business and my long-time subconsultant busy juggling life as a new mom, I’ve been thinking a lot about the different stages of entrepreneurship. 

It's easy to surround yourself with only your peers. People similar in age and going through the same life stages as you. But I’ve found that doing the exact opposite, and making time to connect with fellow entrepreneurs at different stages can be critical to all our success and longevity as entrepreneurs. Here’s why:

20+ 
Work Hard, Try New Things, Make Mistakes

I believe that your 20’s is the time when you should be working the hardest. This is the time to get aggressive about attaining skills. Sometimes you’ll work for free, just to learn, meet the right mentors and gain experience. This is the time to try many paths, and realize that each “failure” or what looks like a dead end, is actually getting you closer to where you are supposed to be. Some of the best business ideas come from a space of flow and not being ridge with how you thought things should happen. In my twenties, I started two different businesses (while working corporate jobs) before my web design company finally succeeded. During this time, I was able to work around the clock, literally knock on doors to find my first clients, and allow myself to get rejected by countless publishers before I got my first book deal. 

30+
Find the Right Work Life Balance

If you choose to have a family, this can be the most overwhelming time as an entrepreneur because your time is no longer only your own. In my thirties, my business grew to two offices, with full time employees. Thinking it would make things easier, I found a business partner and we merged our companies. But that only made things more busy and complicated. During this time, I wrote another book and developed an Internet Marketing class for SDSU all while raising two boys less than two years apart. 

This is when my health took a turn. The pace I was living proved too overwhelming. Constant debilitating migraines from the stress sent me to the hospital too often. I wasn’t able to do anything well in that state.  I knew I had to take a step back. 

I sold my business to my partner and walked away. But entrepreneurship is in my blood. So after taking a very short time off, I built it back up again. This time, under my own name - Holly Berkley Consulting, LLC and simplified everything. I worked from home and had no full time employees. Instead, I relied on a network of subcontractors to help me get projects done. 

During this time, I started writing a 4th book. This one was my attempt to “solve” the work life balance issue. I was convinced there must be SOME way that working moms could juggle small children and running a business. I interviewed at least 50 professionals (doctors, therapists, working moms) looking for answers. I ended up with some solid advice. But in the end, after writing the first 5 chapters, I found the answer. At this time in my life, don’t write the book. It's such a short time when the kids are little. The book can wait. Simplify your time, life, spending, and just be in this moment as much as possible. And that is what I did - and I will never regret those mornings being able to walk the boys to school, or nights snuggling while watching Scooby Doo or reading the same books over and over. So that’s my advice to working moms in this phase of life… do what you need to do to get by, but don’t write the book. The book can wait.

40+
Reflect on The Past but Continue to Evolve 

I’m almost an “empty nester” now. Although I like to use the term “free bird”. As an entrepreneur in this stage of life, it's critical to keep evolving and learning. Especially in a field like mine, where my original web design company has since evolved into all aspects of digital marketing services. 

At this stage, I’ve learned to recognize the wrong type of clients and when to say no to certain business opportunities. I’ve learned the importance of giving back to the community, sitting on boards, and giving younger entrepreneurs a chance to help me with projects - and allow them to teach me as well.

I’m sure there are many lessons still to be learned at this phase, but for now, I think the best part is learning from the past and understanding how to get things done most efficiently. Because the more efficiently you can run your business, the more time you’ll have for living the most beautiful details of life, at whatever stage you are in. 


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Holly Berkley is a professional Internet Marketing Consultant and author of eight Internet Marketing books. She focuses on helping all size businesses increase online sales and dramatically boost web site traffic through proven online marketing concepts. Berkley’s most recent book is “The Social Media Advantage – An Essential Handbook for Small Business” Learn about her latest books and marketing services at www.BerkWeb.com