Being an Entrepreneur: Five Things I Love, Five I Hate

Some months back, I wrote a blog post about why I enjoy working with entrepreneurs.  I myself am a serial entrepreneur and I get a real charge about working with others who have the same mind-set. Most of the time I love having my own company. On my best days, I wouldn’t trade anything in the world for owning a small company and being my own boss.  However, there are other days when being an entrepreneur really sucks, and an executive spot in a big company sounds mighty attractive. Here are five things I love about being an entrepreneur, and five that I hate:

  • The obvious number one benefit is freedom to do what I want. If there’s a potential client I really want to work with, even if the fee level is lower than our normal fees, it’s up to me.  No big agency accounting department or CFO can tell me not to do it. By the same token, if a particular client is so difficult to work with that it makes everyone miserable, I can also decide, “Im mad as hell and I’m not going to take it anymore!” (a quote from the old movie, Network, that those of you who were alive in the ’70s will remember).  I’ve made both of these decisions at times.
  • Every success is more exciting because our small team knows that WE , and we alone, made it happen.
  • I set the rules and if I want to, I can break them. 
  • I don’t have to waste time or energy on office politics.
  • I’m working for my own benefit, not for the benefit of an amorphous group of shareholders.
  • I’m no longer dealing with the big company bureaucracy that used to try my patience and sanity.

Now for the debit side of the entrepreneurship balance sheet, and some tips on how to overcome them:

  • My income can fluctuate a lot. When business is good, I can pay myself pretty well. But during hard times, cash flow difficulties and client cutbacks have a direct effect on my pocketbook. I come last on the list of payments to be made, below employees, rent, utilities and other necessities. The ways I have been able to deal with this are to plan ahead very carefully on both my own and the company’s expenses, and to be tough about getting paid on time. I also bill before a month of work starts, and not after it’s over.
  • I traded company bureaucracy for government bureaucracy (such as the IRS and the NY State Labor Department). I also have a never-ending line-up of administrative tasks that I have to handle as the owner of the company. I’ve dealt with this by outsourcing as much of it as I can afford to specialists, and asking the staff to help with some tasks.
  • One person who doesn’t contribute appropriately to the team has a huge effect on a small staff. At a larger company, sometimes incompetent people manage to last a lot longer than they should because they can hide behind co-workers. There’s no place to hide on the small staff of an entrepreneurial company. There are two ways to handle this: hire very carefully, check references and give potential employees rigorous tests to determine if they have what it takes. And, when I realize that I made a mistake, I try to correct it as quickly as possible.
  • It’s lonely at the top. This is a cliche, but cliches usually have a basis in fact. The best way I’ve found to overcome this feeling is to be in close touch with other PR industry entrepreneurs. I helped found a network of small public relations companies, PR Boutiques International. If I want advice, I go to the other company heads in the group and ask their opinions. In addition, I belong to Public Relations Society of America’s Counselors Academy, which also helps fill this need.
  • Long work hours are a fact of life for an entrepreneur. What I do to compensate is enjoy my time off and not think about work every waking moment when I’m out of the office. I also prefer to take work home and do it there rather that stay in the office until all hours. At least I can work in my pajamas and slippers.
  • It can take a long time to build credibility. Larger, older companies have spent years and lots of money to do this. For the first few years, an entrepreneurial venture has to prove that it’s just as capable as bigger companies and that it’s not going to disappear.  What got us over the credibility phase was doing lots of PR for the company and  stressing the deep experience and capabilities that most of the staff members offer.  Our message was (and is) that we offer experienced, capable professionals who actually do client work.
    Those of you who are fellow entrepreneurs can certainly add to this list. What do you love, and what do you hate?

Lucy Siegel

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6 Responses to “Being an Entrepreneur: Five Things I Love, Five I Hate”

  1. Jennifer Says:

    There is nothing better than being self-employed!

    Choose Happiness & Success!

  2. Ikuji Says:

    Nothing more pursuasive than something out of experience!

    • Bridge Global Strategies Says:

      Thanks, Ikuji. I’ve found out that even if I do a good job of explaining what it’s like to be an entrepreneur, other entrepreneurs learn much more from their own experiences what works for them than from someone telling them about it!

  3. Danielle Says:

    Well said, Lucy! We couldn’t agree more. Being an entrepreneur is great, but certainly not perfect – we call it ‘the good, the bad and the sticky’!

    • Bridge Global Strategies Says:

      Danielle, thanks!

      TO OUR READERS: Danielle Botterell and her partner, Amy Ballon, are “Mompreneurs” who founded Admiral Road Designs ( , an e-commerce venture that makes and sells the BEST personalized fleece blankets for babies and kids (and now makes some for pets, also!).

      Amy and Danielle recently published a book about being mompreneurs, “Mom Inc.: How to Raise your Family and your Business without Losing your Mind or your Shirt” (HarperCollins, February, 2011). The book draws on their experiences as business owners while raising children at the same time, and also tells the stories of more than 200 other mompreneurs. They’ve also been hosting a lunch seminar series in Toronto to offer advice to other mothers who aspire to mompreneurship.

      The book is available either from Amy’s and Danielle’s book website: ,
      from Indigo (where you can download it as an e-book): , or from Amazon.

      Lucy Siegel

  4. Julie Cole Says:

    Well said Lucy! Great points!

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