Sometimes I Ask Myself If The Juice Is Really Worth The Squeeze

One of my all time favorite blog posts is Ben Horowitz’s The StruggleIf you are a founder and you haven’t read it, open it up in another tab for after your finish this post.

On Friday, a CEO I know sent me the following message.

“Brad – I crafted the entry pasted below this morning for my eyes only (and for my own therapeutic purposes), but in thinking about it today, I realized that you’re probably one of the only people I know who might be able to relate or who has interacted with others with similar sentiments. I’m in a good place mentally and it simply feels good to share this with someone else.”

I read it and immediately asked if I could post it anonymously. It’s in the same category for me as The Struggle, but with a different tone. Fortunately, the CEO said yes so I can share it with you. It follows.

Sometimes I wake up and look in the mirror and don’t recognize myself.

Sometimes I haven’t slept properly in days or weeks and I look in the mirror and most certainly don’t recognize myself.

Sometimes I get frustrated that going to bed is like suiting up for battle. I know that many sleepless and restless hours lay ahead before it’s okay to go back to work.

Sometimes I see how physically drained and weak I’ve become. Long gone are the days of being a muscular collegiate baseball player with MLB scouts at my heels or a lean and mean Ironman triathlete and marathon runner. My mental desire to achieve athletic greatness is at an all-time high, but my physical prowess leaves a lot to be desired.

Sometimes I wonder about underlying health issues that aren’t noticeable in the mirror and might not rear their ugly head until years into the future.

And sometimes, I see the disappointing medical test results and wonder if I’m on a path towards failure. Sometimes I don’t even know where to get started to get back on track.

Sometimes I look around and realize that many childhood friends have steady corporate jobs, children and other pursuits. They work to live rather than live to work and they are able to parse work stresses from the rest of their lives.

Sometimes I’m jealous, but mostly I’m lonely and longing for friendship with those who understand how emotionally and physically draining running a business can be. Can’t someone else understand why I can’t commit to an 8pm dinner on a Tuesday night when I’m absolutely drained?

Sometimes I ask myself if the juice is really worth the squeeze.

And sometimes, I admonish myself for such thoughts. My life is not that hard relative to those who have more physically demanding jobs.

Most of the time, however, I love my life and my job has been a source of great energy and inspiration. I know we’re onto something big and the journey has allowed me to surround myself with amazing colleagues and supporters. I only wish that I could find the perfect harmony between health, happiness and my career.


    • Rick

      You should be spending your days watching the great achievements of your team. Let’s be honest that doesn’t always happen. But then maybe you need to pivot or close.

      • Meh, totally stressful leading ones at time though. That can be totally awful. I totally understand the loneliness, and this person does need a support network. I think what Jerry Colonna is doing is great. In Chicago, we have the Junto Institute. It’s very important to have in person people you can reach out and touch, have a beer with, do something with that is not related to work. I’d venture to say only startup CEO’s; or people that once were a startup CEO can fully relate and comprehend what’s going on between someone’s ears.

        That’s the way it was with people like me that trade their own money. No one can really appreciate the stress, or understand it. Can be incredibly uplifting, just like a startup, and incredibly depressing where you want to do anything to make the pain stop.

        • Rick

          “Meh, totally stressful leading ones at time though.”
          Yes stressful. But, I think, a true leader knows that their goals are reached by making the team achieve. The stress should come from outside. Like the team bumping up against walls etc. If the stress is coming from team members then that needs fixed asap before it permeates the whole team.
          A leader should have a plan to reach greatness. That leader puts together a team he/she feels will help them achieve that greatness. The way that is achieved is by directing the team to reach greatness. They are directly connected.
          Just my view.



          • And sometimes depends on how you frame the stress.


          • sometimes you have to change how you look at it. lemons can create lemonade with a little sugar. just make sure it’s not fatal. be a warrior, be able to fight the next day. good warriors often times avoid or retreat from a fight.

          • Rick

            Didn’t Sun Tsu say “Every battle is won BEFORE it is fought.”

          • NEVER BACK DOWN!


          • James Cranford

            i think there was on old warrior saying… ‘live to fight another day’. hoorah!!!! keep giving it to them.

  • Holy shit that was intense!

    I cried like a baby reading “The Struggle” in places.

    The empathy part of my head goes on overload when I read stuff like that.

    When I read “Sometimes I ask myself if the juice is really worth the squeeze”, the following words came immediately to mind:

    “Yeah (or maybe) but don’t throw away the pulp” — whatever that means…

    • That’s where all the fiber is! … of… life.. or something.

      • I actually was thinking of fiber when I said that, LOL!

  • Well… I empathize with what this person is going though, but.. without balance, all is truly lost, full stop.

    I hope this person doesn’t have a spouse and family, because the juice is certainly not worth the squeeze for them. One of the most dangerous things we can do is self-rationalize to the point of distortion. There is always other ways, other paths.

    You don’t go charging up Mt Everest, unless you don’t plan on coming down.

    I wish this person can find the harmony they seek.

    • Rick

      I think this person needs to get a new support system. One that know what a leader should be doing and can help this person stay focused on that even if resources are short.

  • Rick

    The thing I see that stands out the most is he/she says the CEO position is a job. Leadership is not a job it’s a privilege. This is why I’ve said in the past that we don’t have *true* leaders today. People just want the benefits of leadership and aren’t really leaders.
    Also part of the CEO’s responsibilities is keeping healthy and fit. A team without their leader is lost. It sounds to me like this CEO has lost the correct view of what a CEO is!
    Is this another Phat vs Lean issue. Where the leader doesn’t have the proper resources and is losing focus due to spending their day as a worker instead of a leader?

  • Each time I tell myself, and those I love, that I will not do it again. That I will go with the flow… rather than ride the rapids.

    But here I am… ignoring every warning from my past self… doing it all over again. The reality is… we live for the squeeze. The juice is for others.

  • James Balcer

    This post definitely resonated pretty deep. Thanks for sharing Brad and thank you to the person who wrote it.

  • mark gelband

    What gets lost in so many of these comments is the judgement as opposed to the acceptance. We all come at it with our emotional barometer. I am lucky to have been born with the levity gene, and even at the worst moments of my life have felt a sense of positivity and gratitude for my life.

    However, I have been proximate to depression in ways that impact my life and the lives of the people whom I love. I am thankful that Brad continues to advocate strongly for the importance of examining and understanding mental health – and understanding the depths of empathy needed to help in “the struggle.”

    I know I am a better human for Brad’s willingness to explore publicly and for the ability to step out of my own emotional barometer and become a more empathic and compassionate companion – friends, wife, ex, children, etc.

    I wish I could give this person a hug, let him/her know that whatever the outcome, the candor and concern and personal integrity will mean the most. “Perfect” is fiction. Embrace the imperfection of being and do one thing everyday that helps you feel good as human. Kindness and smiles.

  • josh

    Thanks brad for sharing real time struggles, which imho is more helpful than writing about it way after the fact where sometimes there is a tendency to make it sound better/worse than it was. This ceo actually does seem to have more balance than he realizes, because he’s considering both sides of issues- including his most basic and thus difficult to change assumptions- and asking questions and then acting on them.

  • I’ve known some founders that just haven’t taken good care of themselves. No company is worth your health.

    In the “How to start a startup” class at Stanford I believe it was Sam Altman that said founders should focus on:

    Building product
    Talking to customers

    I’ve been going to a hot yoga class for a few years now. It’s such a great break from all the decisions that I make during a day. The teachers tell you exactly what to do (and correct you if you’re doing it wrong) so my brain can “chill the fuck out”.

    And of course my body loves it as it helps offset the amount of hours I sit in a chair with my head in my laptop. Which then helps me sleep better and be physically prepared for spending long hours building product and talking to customers.

  • Ha, that’s funny because about a week ago I stopped squeezing my oranges and started cutting them into wedges to save time but I try to remind myself every day to enjoy the journey.

  • Rob Ryan

    Outsource your body Ben! You know this. Get an amazing trainer and give yourself the gift of 3 hours a week. You’re slaying dragons man, get in shape for it! Im rootin’ for you.

  • Rob Leathern

    There is always someone else competing with you who is willing to trade more of their time and their health for company success than you are: at least that’s the mental treadmill we sometimes get on. Part of it is we just don’t make time talk to others in our circles as much as we should – cofounders, other founders, advisors, even investors. None of these challenges are novel.

  • Rupert Edwards

    I find a 1,000 day plan helpful – where you maintain a focus not just on key life goals, such as launching or growing a startup, but also on key values such as family, fitness, faith etc… Writing out those key goals & values, and getting a day countdown app to help you reflect on both is a big help.

    A year is too short a time to plan and encourages short cuts with your values (ie health or spirituality) and a five year plan is too long. 1,000 days cuts it just right.

  • Rosey

    Thomas Jefferson got it wrong in the Declaration of Independence; life is not about ‘… the pursuit of happiness.’ It’s about ‘The Happiness of Pursuit.’

    If you’re not, to Brad’s consistent narratives here, doing what nurtures your mental health, it’s gut check time.

    P.S. Crap, this just forwarded to me.

    Seriously — share Brad’s blog.

  • Dave Linhardt

    There is a better path to resilience. Take care of yourself first.

    I recognize everything the author said. Among the list of problems, the most concerning to me is the decline in physical, emotional and mental health. Don’t let this happen. Make you the top priority.

    When the cabin loses pressure, secure your mask first before helping others. You aren’t going to be any good to anyone else if you can’t fucking breathe.

  • Dave Linhardt

    And to answer your question, sometimes the juice is NOT worth the squeeze. Startups are experiments with unpredictable outcomes. They don’t always work out. It’s ok to fail. If we knew the answer in advance, it wouldn’t be a startup experiment.

  • Marcus Dahllof

    As a former elite athlete and 2X entrepreneur I can identify with parts here. We had our second child when I started my second company – not great timing, but you cannot chose when to pursue an idea. I don’t think I ever worked out bc I always felt that every free moment should be spent on business, so health and family was neglected.

    Having discussed the topic of performance and efficiency with other smart and successful founders, what it interesting is that most respond with an answer that allows them to wring a few more hours out of each week as if more is always better.

    This is of course contrary to established research on how our brains work – sleep, exercise, diet are critical. And same goes for elite athletes, you need to build in periods of rest, weekly, during training cycles and annually. Rest makes you faster.
    It almost seems like there is an opportunity to create advantage by taking a contrarian approach.

  • Sam

    “The perfect harmony between health, happiness, and my career.” I’m a big fan of the concept of Flow. It’s a moving target – and a lifelong pursuit.

    • Erin Luen Woodbury

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  • OneClutch Lyra

    I feel empathetic. But there’s no stopping time & this time won’t come back either. Live every day trying to achieve some amount of balance and personal satisfaction, work will never stop, it’s you who should come first.

  • Brad,
    I hope you’ll add some of your own commentary on finding the balance, is it worth the effort, techniques for dealing with it, etc.

  • A post that catches pulse of many startup founders. However as we often read that ‘we are about to succeed when we are about to give up’, and if we are making efforts in the right direction, it often pays off.

    Working as employees certainly give us a regular 7-8 hours sleep but does that job give us the same joy as our startup gives – our first customers, the profile and likes, the opportunities when our influencers talk positive about our product and vision, the sense of pride of solving a real world problem?

    A few joys are associated only with founders and losing sleep to cherish that is worth it! 🙂

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  • frank

    it is a new world while it is an old world,every dog has its day,only what we can do is to do something we like

  • onehunglo

    btw that is an old hackneyed saying that we’ve used on wall street for 20 years.

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