Second Half Traversing Strategies

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August, 2017

Long exposure of cars going down the famous Lombard Street in San Francisco.

There may come a time in your second half when consulting, contracting, interim or hourly assignments will be more available, and more attractive, than a full-time job. “Traversing” between leading and doing now will help make you an attractive candidate for such work in the future. This blog will help prepare you for what is ahead.

I use the metaphor of traversing, a skiing term that means moving away from a straight line to a zigzag pattern. During a ski run you may traverse over ice patches, powder snow, or come up against moguls.

Moving up the classic career ladder requires discipline. Traversing requires discipline and flexibility. To do both is to manage two careers — one focusing on employment assignments, and the other focusing on project assignments. One career is called a W-2 relationship, the other is a 1099 relationship.

In career traversing you lead with your skills edge. Your edge gives you maneuverability through different terrain. Once you get used to traversing, the value of hockey great Wayne Gretzky’s comment becomes obvious. “Skate to where the puck is going to be.” Great skiers have the ability to be in the moment on one terrain, while simultaneously anticipating how the terrain is going to change in the future.

Earlier this month this topic came up at an executive career transition networking group where I serve as a resource. We had a lengthy discussion about executives in transition, and the need to stay open to both traditional W-2 opportunities and 1099 assignments.

One argument (mine) was for taking on a 1099 project only after three to six months of a W-2 employment search. This allows sufficient time for adjustment to a job ending, self assessment, market research, focus, and network building.

Most people in transition prefer a W-2 job. When that is the focus, I suggest beginning the process by building a solid bridge to that destination. Securing an early, demanding, contract or consulting assignment can derail a W-2 job campaign.

The executive recruiter who presented at this meeting said he wished he had been open to contract or consulting assignments from the start of his job transition several years back. His argument was that these types of assignments usually result in a helpful compatibility check, and frequently lead to a job offer. “Why not take a chance right away?” was his challenge to the audience that day.

Both of us spoke to the value of 1099 assignments. I am more conservative in the timing of pursuing such engagements. I tell my clients that their networking “flywheel” needs to be fully engaged and keep spinning even if a 1099 assignment is secured. A contract or consulting engagement often means that networking stops, and the flywheel slows down or stops altogether. It takes considerable effort to get it started again once it stops spinning.

I appreciate the recruiter’s belief that sometimes one has to roll the dice and bet on converting a project to a job. And sometimes you just need to pay the bills with a stopgap job. You’ll have to decide for yourself what makes the most sense if you are in transition or anticipating a job departure.

Whenever the time is right for you to pursue a 1099
opportunity, start by considering what employers are looking for: independent project workers, the right expertise, a quick learner, and project leadership. They will wonder if you have the ability to do the work mostly by yourself, without needing much direction or hand holding.

Has it been several years since you have been hands on? If so, it is time to reexamine how you are approaching your work.

At some point in our second half, most of us will want, or need, to shift from the employment track to project work. These 1099 preferences usually come at a time when we want greater independence and employment flexibility, to fill an employment gap, or to improve our cash flow.

If this is what you want in the future, then start traversing between leader and doer roles now. Understand and adapt to what 1099 employers want from you. This will pave the way for your success when the time is right to make your move to a 1099 working identity.

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