‘Come Over to the Dark Side, We Have Cookies’: On Blending Corporate and Freelance Work

After I wrote passionately about making the change from corporate employee to free agent, a friend asked how I could write that when I had just taken a corporate job. I was going back over to the “Dark Side.” Or was it the going back to the “Light Side”? It hadn’t occurred to me that my perspectives and actions might seem contradictory. Let me correct that. It occurred to me, but I didn’t care. And neither should you.

The definition of the “Dark Side” is in the eye of the beholder. Neither the corporate nor the independent side are perfectly good or evil. Cookies or other enticements are never guaranteed, and you can find great risks and benefits in the corporate world as well as out on your own. The key is to know what you want and evaluate your opportunities accordingly.

Who Do You Want to Work For? 

Let’s go back to the reason you’re attracted to being independent in the first place. The freedom to choose when, how and for whom you work is powerful. If you’re going to restrict yourself to one model for the rest of your career, are you really independent?

So going back to the not-so-subtle implications of hypocrisy for my switching sides, the very definition of independence means it’s your choice. There is no hypocrisy in being flexible on how your revenue is delivered — via invoice payment or paycheck deposit. You don’t need to define yourself as a consultant to be independent.

You have the tools to make either model work. Back in the day, the intellectual assets acquired while you worked were applied for the benefit of the company signing your paycheck. Now, we need to get our heads around the idea that skills and experience are, like education, portable. Deployment of those assets can be up to us. It’s how my parents got a 21-year-old me to go to night school for my MBA. As they repeatedly told me, once I got that degree, it was mine forever to use for my benefit.

The Force Has Light and Dark Sides 

Corporate roles help keep me grounded and current in the field. This is important if you want to stay in the independent game for a long time. Things are always changing in our field. Being on the inside allows you to understand how those concepts and solutions play out in reality.

I am seeing more companies supplementing strategic consulting theories and recommendations with solid domain expertise. “Been there, done that” is sought out and worth paying for. You can also cue in on emerging challenges and be ready to offer solutions to clients quicker than other people.

Companies stand to benefit from independents, as well. Perspectives from other organizations and industries is like fresh air in a culture of stale ideas. I can’t begin to quantify the benefits of engaging in your field outside of the company you work for. Bringing the outside into the team by hiring people who have worked at a number of other companies can be an injection of energy. More companies are also seeing the benefit of “renting” niche expertise versus adding permanent resources. Headcount increases are hard to come by, but the need for resources with unique skills is a constant.

Don’t Count on Cookies 

Switching between corporate and independent work offers goodness, but it may be tough to get it. Many companies don’t want to hire people who have been consultants. We are perceived as uncommitted flight risks. This is a head-scratcher. I have seen procurement executives leave critical jobs open for months looking for the “right” person. By the time they complete the hiring cycle, they could have had someone extremely qualified in the role on a contract basis delivering value.

I have seen this changing as companies find themselves lacking depth on their bench. The market for talent is tight, and more highly talented professionals opt for an independent work model.

Tips for the Jedi

If this sounds like something you have mulled over, here are three tips for doing it successfully:

  • Act with intent. Don’t fall into the trap of looking like you don’t know what you want. Decide what you have to gain from an opportunity in front of you. Then decide if it is worth going for. No matter which type of work you choose, make the decision for the right reasons for you and then be confident in your decision.
  • Be open minded. It’s great to draw lines in the sand, but don’t be afraid to cross them for a valuable learning opportunity, great work environment or lucrative engagement.
  • Don’t worry about anyone else’s opinion on the subject — unless they are paying your bills. Then you should probably give it some consideration.

I’ve blended independent work with corporate roles for a good bit of my career. It works because I build on my experience with each successive gig. It also works because I don’t define success as following a straight line to CPO. Ultimately, my goal is to do work that is valuable and enjoyable — and that allows me to save enough money to retire. So give yourself a break if you find yourself switching sides. Do it right, and you can buy your own cookies.

Rebecca Karp is a principal of Sourcing Synergies, a procurement strategy company based in Chicago. Reach her at rkarp@sourcing-synergies.com or on Twitter @rebeccakarp.

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Voices (3)

  1. Ben at HomeWorkingClub:

    I think it’s important, as a freelancer, to remember that the whole point of it is to be diversified across multiple clients. Last year I arrived at a point where I was selling 4.5 days per week of my time to one client. I was on their org chart, I had a team, and I was booking holiday the same as everyone else.

    It was like a trap!

    I eventually had to have a word with myself and remember this was never what I wanted to be doing – but when you get used to the money that can be a hard thing to do.

    1. Rebecca Karp:

      Your point is right on – remember what you wanted to be doing. In my experience that’s the key to being happy with whatever type of work arrangement you choose. And what “independent” is all about!

  2. Naseem Malik:

    Great read and insightful thoughts. You should ditch that friend you mentioned as he appears to be clueless. 🙂

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