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I’m a leader who wants more challenges but I don’t want to overextend. What’s my next move?

Maynard Webb advises a leader at a crossroads to move past the fear.

I’m a leader who wants more challenges but I don’t want to overextend. What’s my next move?
[Source illustration: nadia_bormotova/iStock]

Editor’s Note: Each week Maynard Webb, former CEO of LiveOps and the former COO of eBay, will offer candid, practical, and sometimes surprising advice to entrepreneurs and founders. To submit a question, write to Webb at dearfounder@fastcompany.com.

Q. I’ve put strong leaders in place and am looking to take on new challenges. My biggest fear is that I’m going to get bored with less to do, but I’m also apprehensive to take on more than I can manage. (I don’t think that the CEO will be keen on the idea of me adding some external endeavors like board seats or investing.) 

-Executive at a crossroads

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Dear Executive, 

Congrats on being at this point where you have established that things can run smoothly enough for you to turn to other endeavors. That’s great for the people you’ve empowered and for the freedom it affords you. 

Let’s celebrate that you have climbed the ladder and become successful. But you’ll find that there’s always more to do. At eBay, whenever we got ahead of the curve, there was something else around the corner. Furthermore, just because things are going smoothly now, it doesn’t mean they will stay that way.  In a dynamic fast growth environment, things are always changing.  

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Therefore, it might make sense to keep things as they are for the next quarter or two. See how things develop before you decide what else to add. 

As far as your concern about taking on too much, I find that there is usually a way to get it all done. Sometimes, when I start something new it can be overwhelming, but I can’t stay in that zone for long. That pushes me to figure out a way to conquer it, which is usually possible by setting up systems and metrics and bringing on other people when necessary. The irony is that before long, it no longer requires as much from me and I’m looking for new things to do. And so, the cycle continues. 

Finally, just because your boss may not like the idea of you involving yourself in other efforts is not a reason to abandon the idea. If you do need approval, I would recommend sharing the fleshed-out idea and how you will make this a non-issue for your company. (Basically, you must demonstrate that everything you committed to do will still get done.) If you make a good enough case, it will be hard to deny you this request. CEOs need great executives on their team. I bet you have more control than you think. Also, many leaders understand that an extracurricular activity may make you stay longer in your job and will enable you to bring fresh thinking to your everyday work. 

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