Forcing Function: 90 Days to a Decision

As mentioned previously, it has taken a long time to settle on my next full-time role. Following a period of professional experimentation that turned into full-blown commitment phobia, I have finally given myself a firm deadline: 90 days.

While these past nearly four (!) years since I left my last CEO position have brought the kind of freedom I once dreamed about, I’ve also learned that the risk of paralysis between projects is real and dangerous. With no forcing function to choose a next step, I was guilty of over-analyzing all options and comparing each of them to previous gigs.

No longer the broke, hungry young entrepreneur, I now live in beautiful Marin county, surrounded by soccer games and middle-aged triathletes. I’ve had a whole football team of people to support the navel-gazing lifestyle: therapist, trainer, yoga instructor, life coach, chef (trust me, it goes on in even more embarrassing directions). I had become one of the lotus-eaters from Homer’s Odyssey.

Now whosoever of them did eat the honey-sweet fruit of the lotus, had no more wish to bring tidings nor to come back, but there he chose to abide with the lotus-eating men, ever feeding on the lotus and forgetful of his homeward way.

While some of my guy friends tell me I’m suffering from a severe case of “affluenza,” I’d argue that my problem is not about money, but too much comfort. I had the same issue when I had a “comfortable” job early in my career. The underlying question is: how do you break out of crippling patterns of ease and security. Where does the catalyst come from? I could go on forever in the beautiful ether with no grounding, but would end up medicated in one way or another, possibly becoming the Hunter S. Thompson of greater Marin.

I thought I had checked the box on success and was on to other bucket list items (“Invent next turducken” still not complete), but slowly became miserable. I was at home more often, but less happy when I was there. Outside of family, purpose was fuzzy (no “homeward way”) and I was trapped in the American Dream, filling in life’s gaps with empty-calorie activities.

2013-10-26 11.49.35

And I wasn’t paying enough attention to life’s bank statement to see the shrinking balance. As Seneca said:

“It is not that we have so little time but that we lose so much. … The life we receive is not short but we make it so; we are not ill provided but use what we have wastefully.”

Pity is the last thing I expect. I’m not that self-absorbed. Instead, I’m hoping you’ll help hold me accountable to my time frame and my goals.

I’ve only been “on the clock” for a week, but so far, so good. (“Bought whiteboard: check, Publish blog: check, Have second thoughts about arbitrary timeline idea: check.”)

Reservations aside, I’m awake, purposeful and have numerous interesting conversations going. Instead of considering all options, I am forcing myself to whittle down the list aggressively – make choices, stick with them and figure out what matters most.

I want to get back at it. I miss the fight, the blood and sweat. Climbing a mountain with a tribe. The burning desire to build something is still in me at 41, and I can’t meditate my way past it. And frankly, I don’t want to.

24 Comments on “Forcing Function: 90 Days to a Decision”

  1. Jay says:

    What about teaching?

    • djhersh says:

      Thanks, Jay. Definitely something I thought about, especially being the child of two teachers. It doesn’t feel like the right thing at this point, but I’m hopeful about doing more of it as I get older. Hope you’re well.

      • Jay says:

        Hey Dave, doing well, both boys in college and Emma to follow next year. Not surprising that you’re the child of teachers – give it some thought in the future, you’re a natural.


  2. In other words, you’re asking to be slapped in the face if you haven’t published a post outlining in detail what you’re planning to do next by January 25, 2014 – correct?

    Out of curiosity, Crunchbase indicates that you’re an early investor, you also mentioned yourself that you had invested in Crushpath. From this post, I presume that pursuing the angel investor or VC road full-on is not something that you’re considering to be interesting enough to become a viable option in the longer term?

    Also, what about a full-time philanthropist thing, à la Bill Gates? I guess you also gave that a thought? His big FT interview makes a strong case for that type of choice:

    All this to say that it would be fun during those 90 days to get a glimpse of the options you’re considering (or have already dismissed) before finally settling on your next move.

    • djhersh says:

      Thanks, Guillaume. Yes, VC is interesting, but wasn’t creative enough for me at this point. I enjoyed it, but missed having the control and pride of ownership. Philanthropy is a part of my life and I want it to be more (I’m looking at a few opportunities with nonprofits). Even if I do another company, I will earmark a lot of my money towards charity.

      • What about entrepreneur in residence then? Given your track record, you should be able to get an EIR spot at a top fund, which would mean being able to learn about and interact with cool companies… and swoop in when the time is right 😉

        Jeff Weiner being a good example of this. According to Reid Hoffman [1], Jeff was awarded “founder status” (which sounds what you’re looking for) even though he did not go through all the initial stages of the business (which you might not want to do again).


      • djhersh says:

        Thanks, Guillaume. I’m actually a Board Partner at Andreessen Horowitz (like an EIR but I can do deals too). And coming in early as “Founding CEO” is one of the things I’m looking at with several companies. So you’re right :).

      • Aha! The fun part begins now: which part of the unicorn quadrant [1] will you decide to go after? Enterprise (more likely based on your background, but less new things to look at) or Consumer (shiny new things but much more to learn about)? Looking at the AH portfolio, you could also ask the question seed [2] vs growth [3]. If I may, just print one of those pages out and let a dart decide your fate 😉

        Third option: develop something brand new ouf of your current search (say, the Montaigne Framework for Tough Life Choices Decision-Making (c)) and turn it into a service. More seriously though, this type of quest for meaning / purpose is something that will likely afflict more and more people in industrialised societies.

        With many people retiring at a time when they’re still able to do things, the “now what?” question is going to be more and more relevant. Sure, that’s a space traditionally occupied by charity (serve soup to poor people, help under-performing pupils) and leisure but maybe there’s some kind of marketplace to build for goodwill. Maybe something like Craigconnects [4] for local stuff. Take your phone, launch the app, find people who need help nearby, get a sense of purpose in your life (even shortly).

        Anyway, food for thoughts!


  3. Great post, Dave! I love the more personal insights.

    I wish you luck in finding something that motivates you so powerfully that you can’t believe you haven’t been working on it this whole time.

  4. Pete Eshelman says:

    I have no doubt you’ll come out the other side a better man Dave. Enjoy the ride!

  5. Dave – I ran into this post via LinkedIn. Thanks for sharing this journey publicly. Since you had mentioned the Greeks, I’d suggest Nicomachean Ethics. Best of luck – Doug

  6. Bill Lynch says:

    One of my favorite movies is The Hunt for Red October. Your post reminds me of this quote: “When he reached the New World, Cortez burned his ships. As a result his men were well motivated.” Burn the boats baby!

  7. I have a friend who has fallen into the between-gig paralysis – I fear she’ll never recover! Best wishes to you. The most meaningful word you’ve used here is ‘purposeful.’ That will be your motivation to make some decisions!

  8. Afzal Amijee says:

    Dave – Great post! The search for inner fulfillment and purpose is a continuos journey and not something you can start and stop. The fact that you are aware and exploring the self is in itself a huge step forward.

  9. roger mader says:

    I wonder whether I was party to that early “comfortable” job of yours. Is it too late to get your do-over on the mac-n-cheese holiday disaster?

    And as long as Bill is throwing out favorite movie quotes, I’d suggest you hit rewind on The Untouchables for that blood-soaked denouement on Sean Connery’s Southside Chicago apartment floor, sputtering out his last words as a provocation: “What are you prepared to do!” (Maybe you can get your chef and yoga sensei to collaborate with your voice coach to let you roll around on some ketchup packets and spit it out in his Scots burr.)

    • djhersh says:

      Thanks for all the support, Roger. The job I was referring to was the HP gig (solo consulting). You guys didn’t pay me nearly enough to be “comfortable”.

  10. pdxgardenblog says:

    Looking forward to seeing what you do next, Dave! You had a lot to do with the magic in the early days of Jive and I’m sure you can recreate that again if you set your heart to it.

  11. Paula says:

    41 isn’t so “old”, Dave. You are just getting started. Chapters end and a new sequel begins. Keep it interesting. It just gets more dramatic–urgent. Finding quality of the moments with a view to tomorrow. I admit it’s a challenge, though. Good idea about the deadline, though. The “death line” just keeps getting closer.

    Keep ’em coming (I.e., your blog installments).

  12. Conor says:

    First, let me congratulate you on both your thoughtful blog, as well as all your success. It seems to me that you are on the precipice of an exciting new phase of your life, where anything is possible, but nothing is very clear. As an artist and a writer, I am well aware of this sensation. Practically every day of my life is devoted to filling in the blank pages and empty tableaus of my life with whatever my imagination can conceive.

    Now, I am not qualified to be CEO of a lemonade stand, much less a multi-national conglomorate, but I do know that life has a purpose for us all. Many never fully realize that destiny. Yet, there are those who continue to strive to reach those distant realms of mystery and the elusive unknown wonders that have yet to be chronicled. History confers upon those individuals the mantle of greatness. You certainly have the ability and fortitude to be counted among their number.

    I can certainly relate to your current malaise, as I have felt that way myself. That internal striving that urges us to go on, and not be content with what we have achieved. Although I have accomplished many of my own goals, the larger ones that I have carried with me since childhood remain unfufilled. However, I have always been resolute in my determination, and fiercely intolerant of anyone who would stand to hinder me in any way. So I would suggest thinking about what you would like to do, what masterpiece do you want to create? Then, go find a way to make that dream into a reality.

    Sometimes life is not fair, and our hopes may be dashed. But dreams can never truly die. In my life, I have had the privilege of knowing many extraordinary people. I even knew you once in, almost literally, another lifetime. If not for the kindness and charity of you and your friends, I would not be here today. You actually saved my life. Which means that your life has played a part in the lives that I have been fortunate enough to have touched in the intervening years. Any success, joy, or wonderment that lies in my future will have been due, in some measure, to you.
    We never truly know what life has in store for us, or what a large impact the tiniest gesture can make on an incalculable number of individuals. This is what inspires me to continue seeking the answers to my artistic restlessness. I wish you nothing but good luck and great fortune as you continue your journey into the unknown mysts of a future waiting to be discovered.

  13. […] Forcing Function: 90 Days to a Decision → […]

  14. […] pursuit of this work culture nirvana, I came up with the following personal tenets for my next gig. Taken individually, most of these points are about as original as an NBC sitcom plot, but […]

  15. […] pursuit of this work culture nirvana, I came up with the following personal tenets for my next gig. Taken individually, most of these points are about as original as an NBC sitcom plot, but […]

  16. […] with the clock ticking on my continuing search, I made a decision: no matter which gig emerges on top, the money I make […]

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