Reality Bites: Facing the Reality of Starting a Business

By Carol Cassara – Contributor & Midlife Wrangler

This is not the post I intended for this month, but I had an experience so powerful that I simply had to share it with you.

I went to a networking event. Not online. In person.

Reality CheckYes, it was on my  “SMART goals plan” and since I am accountable to those who are reading this series, I got up, dressed and off to this event. It’s been years since networking events appeared on my calendar. This was a group of about 25 women entrepreneurs, my age, older and younger, but what we had in common was the desire to make a dream come true: our business.

When I thought about my dream of a workshop business, it was always in amorphous ways. Women would sign up, I’d give great content, everyone would go away happy. And even after my survey and drafting my plan, the reality of a workshop business remained at arm’s length. Hey, I teach business in an entrepreneur program. I know what it takes, I thought.

But then, I came face to face with not just the theory of starting a business, not just the academics, but the reality, as experienced by other women in my city.

The day’s speaker had started a number of successful small businesses, and her presentation was about building referral sources. Her method was well-thought out, detailed, aggressive –not for the timid—and it worked. It was also super-time consuming and made short work of any lingering “nice girl” limitations any of us might have.

A little frisson of…was it anxiety? concern? foreboding? ran up my back.

Later in the meeting, we introduced ourselves, our businesses and said what we needed from this networking group. Several women spoke about business being slow and revenue being down. One woman’s business was down 75 percent year-to-year. Another was trying to get more business while facing hormonal emotions from her pregnancy. She was on the verge of tears. Others asked for help with outbound sales idea. Some had absolutely no idea how to connect with potential customers. Or how to close a sale. Everyone was candid about what we needed and many of us stepped up to offer ideas and assistance.

As each woman spoke, my discomfort grew. I had some of those skills, no question. Maybe even most of them.  But here’s what I wasn’t sure I had:  the will to do the work.

Sure, I’ve made many dreams come true in both career and life. But secretly, I’ve always believed the Universe had a bigger hand in it than I. Sure, I knew how to identify and leverage opportunity. But maybe, I worried, my role was far smaller than the role of fate or destiny.

These women were completely committed to the success of their ventures. It was how they wanted to make their living. For some, it was clearly a passion. For others, something they fell into.  But for all, it was one boatload of hard work.

Now past midlife, I wondered if I really wanted to wrangle with all of this. I’d already retired after a 35-year career. I’m passionate about my time-consuming part-time job teaching business to college students. Just teaching two classes a semester fills at least 30 hours per week—a significant time commitment. What about my memoir in progress? I was paying far less attention to it than I had intended. My daily blog? My voice lessons? The essays I like to write? And time with my friends? Social media? And, for God’s sake, what about my husband?

What’s more, I’m a little bit lazy at this stage in life. I like to relax with a book. Or watch Mad Men or Downton Abbey.  Is there really room for it all?

A reality check, that’s what these entrepreneurial women gave me, by talking about all the facets, considerations and activities that drive a successful dream.

A reality check on a dream? Yes. Dreams stay dreams until they’re made real, of course, the details of which I’d previously shrugged off.

This is where the rubber meets the road.  Where your dream is really tested. If it’s really something you’re passionate about, then you’ll move heaven and earth to make it happen. The idea of hard work won’t put you off –nothing will stand in your way–because you know it’s going to pay off with that big reward: self-actualization.

For me, well, that meeting was my moment of truth. How committed am I to this workshop business, as opposed to the many other things I’m involved in?

It was time for me to get serious. There isn’t time for it all. What did I really want?

Have you had a defining moment when your commitment was tested? If you have, I’d love to hear about it in the Comments section.

Carol CassaraCarol Cassara is a writer, blogger, college professor and former corporate executive who is busy making her own dreams come true. In 2009, she remarried her first husband after they’d been divorced for 27 years. Naturally, with a story that good, a memoir is in progress. She, her husband and two dogs live in the San Francisco Bay area. You might know her as Middle-Aged-Diva, but she now blogs at

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4 Responses to Reality Bites: Facing the Reality of Starting a Business

  1. Kate says:

    Both my husband and I were laid off at the end of last year. While I have tossed around the reinvention idea, he is determined to going back to the type of job he had. I’ve been to some networking events and was befriended by a woman who had been in my position. She and her laid off husband started their own home-based business and put the ? to me if this was something we had thought of.
    And you know, the idea has crossed my mind. The timing would be right since we’re empty nesters and both out of work. And the thought of being in control, being my own boss sounds wonderful. Problem is…what the heck would that business be? Even though we have been happily married for more than 30 years, we do not have all that much in common so I couldn’t think of something that we’d both enjoy transforming from hobby to work.
    It’s very frustrating!

  2. I hear you both. Tahnya, I feel like I’m still a work in progress, trying to define what really floats my boat and sometimes, it’s surprising. I don’t know why I’m shocked at how much work it all takes!
    Kate, partnerships are kind of like marriages. I tried partnering w/ friends twice and failed–and doing it with my husband would terrify me!! You know, if one of you had a passion and the other one had a skill they didn’t care what they applied it to, it might work out. Sometimes, though, familiarity is like a warm blanket and what we know is familiar and comfy.

  3. Kim says:

    Great post. Really, really, great post. I have had this dream as well, but with an aging mother, kids, household responsibilities, PTA, a blog and yes, a husband, I just don’t see how I would have the time or frankly the drive for the commitment required. I also, like you, believe that if that is what the universe has in mind for me, I will be led down the path. Phew, maybe it’s ok to just dream for now!

  4. Thank you for your honesty- I am with you, lady. I dream and I work and I struggle. I see women (and men) around me work, and dream and struggle. I’m not sure there’s a formula for true success. I see people be aggressive, I see people creating a great product- but from my pov, I am seeing so much struggle- it takes a lot, including a good business plan, and good luck to make it in a tough economy. I have no Plan B, so I keep working at making working for myself work. But whoa, Nellie, I am in over my head. It is refreshing to see/hear an honest voice about it as most people seem to mask and “fake it till you make it,” making others wonder silently to themselves if its just them who are struggling. It is not. I appreciate your candor. Whew.

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