Dilemma of the Self-Employed: Will I Ever Be Able to Work for the (Wo)Man Again?

This fall will mark the 10th anniversary of my business, . I’m part of the huge, virtual shadow army of Silicon Valley: the consultants and contractors that bring in their expertise for a project or to help a company get off the ground the right way.

I am typically engaged with three, four, and sometimes six companies at a time, and I bring in other parts of the army so that my clients get the fastest, best business results at the lowest possible cost. This model has become business as usual for a lot of my clients and their Silicon Valley competitors, but once in a while I remember that it’s the front edge of a huge wave that’s changing the global economy.

I can’t believe that I have been at this for almost 10 years. I have NEVER done any one thing for 10 years. So it’s not surprising that once in a while I ask myself if there’s a point in time when I should start thinking about taking the job calls that are still coming my way.


The big pluses of being a consultant:

  • Every client brings new learning and new ways of doing things. It’s very rare for me to be bored.
  • The money can be quite good if you’re disciplined and play your cards right.
  • Flexibility and flexibility. Don’t get me wrong; I have lots to do. But when I do it and how I do it is totally up to me.  Or not do things and go on a long vacation instead. ( Like the one in the photo to the Cayman Islands)

But of course there are minuses too:

  • With the flexibility comes responsibility. And responsibility means doing whatever it takes to get a project done, often at the expense of sleep and personal time.
  • To keep the revenue flowing, you always have to be selling. And the critical time to do it is when your project is at its peak.
  • The mix of work I do is often much different than what I would do if I were still an employee. I know of at least one fellow consultant who went back to the W-2 side of the house just for that reason.
  • With some notable exceptions, I typically don’t build the same kind of relationships with my clients that I had with my co-workers. (Good thing many of my former co-workers are still in my life and are often clients. J)
  •  And no matter how disciplined you are, the consulting life brings some level of financial uncertainty. From unpredictable forecasts to slow months, last-minute project cancellations, tardy payments, and even bad debt scares, I have seen a lot.
  • I am a tough boss. Maybe the toughest.

For now, the balance of pluses and minuses is still weighing heavily into the consultant camp for me. I love being in the shadow army. It isn’t for everyone, but if it works it can work very, very well. :-)

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