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, Giant Stride Marketing Group. 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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