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4 things managers can learn from top freelancers

I am not a business coach. But as life in corporate America changes, I’ve become one version of many of my C-suite clients who now find themselves in a job-holding pattern. As the world changes under these managers, they suddenly have the power to learn from the lessons I’ve learned over four decades of navigating the not-always-certain type of freelancers.

Maybe the new CEO is reducing your role or changing your title to improve your output without a big paycheck. Maybe you’re waiting for the stock to wear off or you’re struggling to find the right new position before you move on. In any case, you are not comfortable in this unfamiliar role: You feel stuck, instead of just neutral.

Because managers are highly successful people whose jobs are often sequential, they look at success in black and white terms. My job is to help them survive in the dark, using advice based on the confidence and tenacity I’ve gained from my 40 years of freelancing.

Top tip: Save yourself

I tell my C-suite clients that I had to learn the hard way that you can’t care more than they do. (“Them” is anyone in a management position you work with.) Whether your instincts and experience in projects are being ignored due to CEO ego, corporate groupthink, or data blindness, your job is not to save that project, but to save yourself. Respect yourself to hold the right audience for your ideas. It’s impossible to motivate the uninterested, and trying will make you feel like a failure when you never had a chance.

Top tip: The takeout value

To paraphrase Hunter Thompson, you bought a ticket, now get on. You’ve done the work to earn your place in the room, so now you have to find ways to continue to extract value. This is not a Quiet Quit. It’s actively accepting where you are now and making an effort to reap the benefits that undoubtedly exist—because there’s always something useful, even in difficult situations. If there’s a lack of good communication with your C-suite colleagues, direct your energy to the people who report to you—those who might value your experience. Ask for regular consultation sessions just to hear their ideas, participate in their project development in the early stages instead of waiting for fully baked ideas to land on your desk, make time to become a better consultant. This will not only enrich your current situation, when you move to another management position, you may find yourself needing their skills, which you now understand better; and their loyalty, which has now been earned.

Top tip: Climbing achievements

Equating your success with the successful completion of the team’s vision will break your heart. You have to find value in incremental implementation. If you can’t control the final implementation of the project, it helps to break your process from concept to implementation down into stages and acknowledge your success at each stage (to yourself). That way, even if the idea doesn’t work out the way you thought—and it is rare-you will still feel satisfied, instead of judging your success by the second job of others.

Top tip: Highlight the reel

Make sure you create a highlight reel. In addition to the multi-page resumes they already have (which most people won’t fully read), I encourage my older clients to create a one-pager that focuses on what they do best. Their greatest strength. This clarity helps them—and their hunters—guide their job search. To make the information easier and more interesting to read, I always suggest that they hire a designer. The good one. Because these days, you are your own marketing image. Invest in your storefront.


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