Golden Handcuffs

What happens when you want to do something, but feel held back by the money? In our work, this most often shows up as golden handcuffs, when something we no longer longer wish to do brings in a level of financial stability that makes it difficult to walk away.

There were a few questions submitted on this topic—and it's a good one— so I'm going to address it here.

I have personally come up against this many times, both as an employee and an entrepreneur. Before starting my own company, I was a partner at a creative agency in New York. I made great money and the agency always seemed to be on the brink of being acquired—which could have been a nice payout. This lead me to stay on longer than I actually wanted to, waiting.

In my decade plus of entrepreneurship, I have created and brought to completion many offerings, offerings that took real effort to build, but that— when I felt they had run their course— I decided to shift away from and onto something that felt fresh and fun. Even if these offerings were still lucrative, some of the were simply not worth keeping because of the amount of time and energy they required of me. For instance, for many years I ran a conference in New York. There were lots of things I loved about it, but as the conference space became more saturated and the game of sponsorships more transactional, I realized I didn't love that work enough to stay in it.

Here are three things that have helped me in situations of "golden handcuffs":

1. Recognize that downsizing is a valuable tool to up-leveling your life. Our culture likes to teach that success is linear and if we're not always doing more, making more, and having more that we are failing. But this simply isn't true. There are so many intangibles that add richness and value to our lives. Perhaps it's the joy of doing something that lights you up, or the extra time you have, or the ability to choose your clients and projects if you go off on your own. These things matter, even if they don't have a dollar value. So when it comes to money, perhaps the number you think you need isn't really the number you actually need—for now. Perhaps you could live on less and actually be more satisfied? It took me a few years once I went out on my own to make the same income I made at the agency. But then I kept going, doubling and tripling that number.

2. See what can be automated. You want to make money without sacrificing what's most important to you, so if there's a way to do both then you've hit the sweet spot. Often this requires some creativity and an unconventional approach. How can you lighten the load of something that's income producing but a total time and energy suck? If you're an entrepreneur, maybe it's something you format differently, or automate? If you're an employee, maybe you can secretly outsource a part of your workload? (I loved how in one of Tim Ferris' books he tells the story of the magazine editor who hired someone overseas to do all of his research without his company ever knowing).

3. Have a plan and remember that it's a build. Having a plan on how you'll make money in a way that feels more aligned to you is important because it both helps you feel secure and it instructs you on what you need to do next, so you're not flailing around. This plan will not be akin to flipping a switch and suddenly making the exact amount of money you desire (though sometimes it is). More commonly, this plan is what you are building toward, and this build takes time. Give yourself the grace and understanding of this so you're not in the pressure cooker desperate to make all the money at the get-go.

Remember, you're not just building a business, you're building a life. You get to architect it in the ways that make you feel like the best version of you.

And—if you would like support in building out your plan, this is exactly the sort of work I do with my clients in 1:1 clarity sessions. More below if you're interested.

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