When the Juice Isn’t Worth the Squeeze: Rethinking Work & Life

by Matt McCall

A lot of people are re-evaluating their career and life choices. As the markets continue to correct and gyrate, more and more people I coach or talk with are increasingly questioning their current path, occupation, or approach to life. The juice is not worth the squeeze. I wrote about this cycle in Managing Life’s 8-10 Year Cycle. In most of these cases, these people have either made poorly thought-through career choices or have the wrong approach/perspective for doing it. Fortunately, this reflection is positive, and the path forward is straightforward.

“What are you going to do with your one precious life?” – Mary Oliver

I was recently reading a post by a very disillusioned, younger venture capitalist who talked about venture being an exhausting, all-consuming, and “thankless” job with poor monetary outcomes for most (including him). Yet, he was heroically going to persevere (I’m not certain why). We’re entering a period of reckoning in venture. There are a lot of tourists in the business—people who came in when capital was abundant, momentum investing was easy, and losses were rare. Venture firms exploded from 1,200 in 2015 to over 6,000 now. Today, there are over 55,000 venture-backed companies, many funded at inflated valuations. But there were only 25 IPOs last year, and exit multiples are down 70%. You need to approach your career like a professional athlete. Tourists will be fed to the wolves. If you’re questioning your path, you’re not alone… and that is not a bad thing.

Be Clear Why You Are Doing Your Career

This moment is a powerful invitation to revisit why you do this work. Many venture capitalists joined to be involved with glittery start-ups and take home 7–8 figure paychecks. This will end in heartbreak for most. In its truest form, it is a creative art, being in service to the heroes we call entrepreneurs. The more you’re in service to them, the more fulfilling the work becomes—and, often, the more successful your outcomes. Venture is not a materialistic game (yes, it has materialistic outcomes), though many treat it as one. Both John Wooden and Nick Saban drilled into their players that they needed to focus on the daily, disciplined process and not winning a National Championship. The latter comes with the former. When approached purely for external validation and rewards, it’s easy to lose meaning, joy, and connection. You will feel like you are being waterboarded.

Key Factors for Success & Contentment

Successful professional athletes and star business performers who thrive in the crucible of competition focus on a handful of basic tenets. In my Good Life class, I tell my students (and entrepreneurs) to LIVE VERTICALLY, NOT HORIZONTALLY. Focus vertically on actualizing your highest potential (Maslow) or closing the gap 1% each day between you now and your highest version (Aristotle). Be intentional about what your strengths and values/energizers are (what you have a right to win at), be curious about how to get better, seek mentors and best-in-class resources, be disciplined each day at growing better, and do so for something that is not your own glory or profit (service to something greater). This last one is not selfless… if nothing else, people are more positively predisposed to you and more likely to proactively bring things to your help if they feel you care about their well-being or journey. Focus on what you can control (your process and your habits).

However, most people, including many venture capitalists, focus horizontally. They are constantly looking sideways: comparing themselves to others, assessing themselves based on financial outcomes, seeking approval, focusing on how they appear and not what they are doing. They focus on their own gain versus the value they bring to others. They seek to become enough, and when things don’t go as planned, they conclude they aren’t enough instead of appreciating the learning experience they just had. The Imposter Voice roars.

As you do this, you need to understand your derailers. What are your tendencies that derail you from achieving what you hoped to achieve? We all have a very predictable set of these that show up frequently. Be aware and watchful for these, and create routines or habits to address them.

Strengths, Values and the Why

Be very clear why you are doing something. Be certain it is bringing value to others, helping them make progress in life, and reducing their suffering. Surprising and unexpected goodness comes into your life when you do this. Call it the Law of Karma or call it common sense. First, people will pay more for more value. Second, people will help you or think of you if they view you positively. Third, you will have closer relationships. If you are doing it solely for financial gain and view others as a means for you to get wealthy, things get dicey fast. I’m not saying that you shouldn’t be interested in making absurd amounts of money, but make that the outcome, not the input.

Also, make certain that you are doing something that you have a knack for. Know your strengths (ton of tests around this), and make certain that you are focused on tasks that take advantage of them. If you have a great forehand, make certain you set the tennis match up to move the ball to your forehand. Many people do things because they seem like a respectable career or there was a ton of money or their family/friends approved… not because they were good at it. A friend of mine went into law because his father and grandfather were in it. He hated every minute of it despite success.

Also, focus on careers and activities that energize you and that you value. I was listening to an aerospace CEO talk about how he woke up one day doing digital e-commerce and asked himself if this is what he wanted his life to be about. He had an obsession with the Concorde since childhood and bringing supersonic travel to the mainstream. This has gone very well for him. Start-ups and venture are not easy. It is a pit fight, as the above VC mentioned. Make certain you want to take on the challenges and surprises of entrepreneurship because you love creating, love helping entrepreneurs, love people, and are curious as hell about everything.

“He who has a why to live can bear almost any how.” – Friedrich Nietzsche

Focus on the Success Drivers

Get curious about what the best in your field do. Seek the top mentors you can. Read about the elite performers (but focus not on what they achieved but on their habits, discipline, networks, and unique approach… what made them successful vs. others). I’ve been successful in venture capital because I lean with curiosity into how to be the best VC. I’ve had horrible periods, fantastic disasters, and am riddled with truckloads of flaws. However, the more I looked at other successful VCs and entrepreneurs, the more I realized VC is about power networks, storytelling, thematic focus/contrarian thinking, disciplined valuation models, fundamental skills around scaling, and being empathetic—leading with random acts of kindness. I’ve tried to find the best people in each area and learn from them. I’ve realized that good VCs are consiglieres who seek to be the best guide/coach in service to their entrepreneurs. At any point in time, I’m unleveled in some way. For example, I’ve spent the last ten years doing coaching training across multiple performance and philosophical platforms with one goal: how can I help my entrepreneurs “manage the demons that haunt them on a Sunday night.”

More importantly, I work hard on trying to manage my own internal triggers, to focus on being in service to the founding team, and to try to show up for the entrepreneur. Being a VC early in the first ten years, often in one’s 30s, is the toughest, as you’ve not had the wins to quiet the imposter voice inside, but yet everyone around you is marketing their amazing successes. Focus horizontally on your life relative to theirs, and you will almost always be disappointed. Focus vertically on getting better and better and better at self-management and the art of venture in service to your entrepreneurs, and you will always have a sense of progress/contentment. You cannot control how the former goes, but you have complete control over how the latter goes. You can’t control the outcome, but you can be relentlessly disciplined around the process. Input, not output. Take control of your own happiness.

The Three Truths

My coach, Phil Stutz, says no one is absolved in life from the three truths (Pain, Uncertainty & Constant Work): it will not go the way you plan, the path forward will be opaque, and it is constant effort—the clock resets to zero every morning. Entrepreneurship and venture capital are this on steroids. As a result, clinging to the outcome (living horizontally) or demanding certainty is a fool’s errand.

Give a Shit About Others

The people who survive in venture for three decades, like I have, learn to show up with empathy for and commitment to their CEOs. You can have very frank and intentional discussions with your teams, as Darwin is a very real presence. However, if the deal is not going to work out, my being an anxious, self-focused prick is not going to make it better. I’m also not going to be thinking about venture from a place of fear, but rather from a more rational, prefrontal cortex, grounded place. As Warren Buffett says, things get a lot clearer when you do this. This is not easy and is a life full of work.

Be the Broom Guy in Front of the Curling Puck

Focus on others and their journeys—what they are trying to achieve—and help. Be the broom guy in front of the curling puck. A very simple framework for managing the relationship is to start with empathy (“Wow, that sounds like you had a rough month in sales (or a great month). How are you doing?”) and simply hold space and actually give a shit & listen. Help get them to ground. Make certain they feel seen and heard. Then you can have the frank conversations around what actions to take to move forward. You will also have better and more complete information to make decisions from.

However, if you show up from a place of scarcity or control & command, often driven by fears around having to communicate to your partners or your LPs, you are going to trigger and start a very negative cascade as you engage with the entrepreneur.

Conclusion

LIVE VERTICALLY, NOT HORIZONTALLY. This has been the conclusion reached for thousands of years, going back to Aristotle and Marcus Aurelius to top coaches and the Navy SEALs. Start by laying out what you are good at and what energizes you (ton of assessments & exercises for this… see past posts). Be clear you want to join the battle. Find the best, get curious. Be disciplined & intentional in your approach. Give a shit about others and seek to bring value to them. If it were easy, everyone would do it!

06/27/2025