Hello friends, and welcome to this week's musing from Stone Ridge, NY! As I’ve been taking in the vibrant and blossoming pink Dogwoods and gold Forsythias on my daily nature walks in the Catskills, I'm struck by the power of spring to inspire new beginnings and fresh perspectives. The world around us has awakened from its long slumber, eager to welcome everything the new season has to offer.
Speaking of embracing new beginnings, I'm currently in the process of taking stock of all the projects and responsibilities that have been occupying my headspace over the past six months. I’ve sensed that some pruning is required to make way for new growth. In this new season, I'm reminded of the importance of letting go of what no longer serves me.
As I reflect on my own priorities, I’m hitting pause on the podcast after next week’s episode to focus on my true passions: coaching and writing. Both have been thriving beyond my wildest expectations, and I want to double down on what's been energizing me and working. Although it's a difficult decision given how much energy and time I've invested in the podcast, I feel inspired to continue to improve as a writer and a coach, and make an even bigger impact in those realms. I also realize, as a solopreneur and father of two, my time is incredibly limited; focus is a powerful forcing function.
And speaking of making space and writing, I'm in the early stages of contemplating a book project that explores the topic of change and transition. It's a creative challenge that both excites and intimidates me, but I'm eager to learn about book publishing and dive deeper into the topics I’m so passionate about.
If any of you have experience writing a book, working with an agent or a publisher, or simply dream of writing a book, I'd love to hear from you.
Now onto this week’s essay!
Scrolling through social media these days, it's hard to avoid the barrage of advice about quitting our jobs and embracing the pathless path. But for those of us who have crossed the midlife passage, the prospect of making a significant career change can seem frightening and daunting, if not downright impossible. Unlike the young millennial thought-leaders and their followers, many of us have marriages, multiple kids, mortgages, and decades invested in a particular identity and career path. The stakes are higher, and the risks of making a change can feel overwhelming.
Some people are fortunate to have earned the freedom and flexibility to take a three month sabbatical, work remotely from Bali, and tap into their savings to discover their next calling. But for the vast majority of us in midlife, the reality is far more nuanced and complex. We may feel trapped in our current careers, overwhelmed by family obligations, and unsure of how to make a change without sacrificing our financial stability. We may be afraid to let go of our hard-earned expertise, risk our social standing, or disappoint loved ones and colleagues by straying from the path we've been on for decades.
At times, we may find ourselves daydreaming about a new future, only to become paralyzed by the thought of dismantling the foundation we've built over many years. Or we may be too fatigued at the end of a long day to even find the mental space to think about what's next. We may catch ourselves saying things like, "But I've invested all of this time in my career," or "But then my partner will need to get a job," or "I can't possibly start over," or "What would I even do next?" These factors and big questions create resistance when considering a major career shift at this stage of life.
If you’re feeling this way, I want you to know that you’re not alone and there’s nothing wrong with you. I’ve been there before.
And every day, I have conversations with high performers in midlife who are no longer energized by their jobs or feel like they've hit a plateau in their careers. These are people like a community leader in crypto who dreams of becoming a doula, a senior executive who longs to open a bike shop in Maine, a VC who craves to build a firm with partners who share similar values, and a decorated chef who fantasizes becoming a painter and settling in the countryside. Countless others have reached out to me, feeling like they're going through the motions or suppressing how they really feel just to keep going.
These individuals have all tasted success and could easily reap the rewards by continuing down their current path, but something doesn't feel quite right in their bones. They're caught in a dilemma because they have others relying on them and have built a life based on who they thought they wanted to be or had to be. The idea of excavating the foundation they’ve built is downright terrifying, and they’re left questioning whether it’s worth the risk.
Well, I have some good news. Many of us in midlife are grappling with the same questions and fears. But despite the challenges and strong emotions, it's not too late to carve a path forward that pays the bills and aligns with your values, interests and innate gifts.
Time is one of your greatest assets, even though it might not seem that way. If you’re 40 years old, you’ve already worked more than 36,000 hours in your career, assuming a 40-hour work week. That’s a significant investment of time and effort. However, if you plan to retire at the “standard” retirement age of 65, you still have 50,000 hours of work left in you. 50,000 hours! In other words, you’re not even halfway through your career yet. You have plenty of time to pivot and change paths, more than once.
You're not alone if you find yourself asking, "Where on earth do I even start?" It's a daunting and complex question, and the answer is based on many variables, including your financial picture, risk tolerance, family composition, values and ambitions. But fear not—I have a straightforward and practical solution to help kick start the process: experiments.
Experiments Illuminate the Path
Navigating a midlife career transition can feel like wandering through a dense forest without a compass or map. I know this from personal experience—my own journey lasted more than five years, during which I struggled to find my bearings and make sense of my options. I often found myself clinging to what was familiar, afraid to stray too far from the path I had been walking for the previous decade. This fear and uncertainty slowed me down, leaving me feeling stuck, confused and unfulfilled.
A couple of years into my odyssey, I was immersed in Great by Choice, by the renowned author and researcher Jim Collins. There, I stumbled upon a powerful metaphor he referred to as "fire bullets, then cannonballs.”
“Picture yourself at sea, a hostile ship bearing down on you. You have a limited amount of gunpowder. You take all your gunpowder and use it to fire a big cannonball. The cannonball flies out over the ocean…and misses the target, off by 40 degrees. You turn to your stockpile and discover that you’re out of gunpowder. You die. But suppose instead that when you see the ship bearing down, you take a little bit of gunpowder and fire a bullet. It misses by 40 degrees. You make another bullet and fire. It misses by 30 degrees. You make a third bullet and fire, missing by only 10 degrees. The next bullet hits—ping!—the hull of the oncoming ship. Now, you take all the remaining gunpowder and fire a big cannonball along the same line of sight, which sinks the enemy ship. You live.
This concept swiftly became a guiding principle as I navigated my own transition, conducting experiments, dipping my toes into uncharted waters and seeing what I learned about myself.
From that moment on, I embraced this concept, and focused my energy running experiments to illuminate the path forward. With each experiment I conducted, the more valuable information I collected about myself and the world. And with each additional insight, I felt a growing sense of clarity and confidence. Through dozens of these explorations, I gradually uncovered what energized me, what truly mattered, and possibilities lie on the horizon. Most importantly, I discovered what paid the bills so I could support my growing family. With enough time, I was ready to fire my cannonball.
From the outside, it looked like I made a monumental and rash decision to abandon the lucrative and comfortable world of venture capital. But, internally, I had all the evidence necessary to confidently take that leap of faith. I knew I was going to succeed because I had the experience and data to prove it.
Career Experiments: A Brief Primer
Think of experiments as small, manageable actions you can take to explore possibilities, opportunities, interests, and passions. They answer hypotheses and questions about who you are, what matters to you and what you enjoy. These explorations don't require a significant investment of time or money, but they provide valuable insights that will open doors and reveal unexplored domains and parts of yourself.
The beauty of these experiments lies in their simplicity. Maybe you've always been drawn to pottery, so you sign up for a local workshop. Or perhaps you've felt called to help others, so you begin to mentor recent college graduates. The goal is to try new things, see how they resonate with you, and learn from these experiences.
When it comes to designing and running a good experiment, consider the following factors:
Relevance: Align the experiment with your interests, values, or potential career paths. It should provide insights into areas you're genuinely curious about or have a passion for.
Manageable scope: Keep the experiment within a reasonable size and timeframe, so it's easy to execute without overwhelming you or causing significant disruptions to your life. This allows for more flexibility and the ability to test various options.
Measurable outcomes: Design your experiment in a way that allows you to evaluate the results, whether it's through personal reflection, feedback from others, or any other tangible indicators. This helps you understand the impact of the experiment on your life and make informed decisions.
Adaptability: Be flexible enough to adapt the experiment based on the insights or outcomes you've gained. This enables you to iterate and refine your approach, moving closer to your desired outcome.
Learning-oriented: Focus on what you can learn from each experience, regardless of the outcome. This encourages continuous growth and self-knowledge.
Actionable insights: Generate actionable insights that inform your next steps, whether it's to pursue a new career path, develop a skill, or explore a different interest.
An effective experiment serves a dual purpose: it either validates the inklings you've had all along or generates critical insights that steer you away from a particular direction, indicating it's not the right fit for you. For example, I walked away from my venture fund after feeling what it’s like to coach while also angel invest on the side. I realized that pitch meetings and networking for deal flow drained my spirits and energy. Here’s my point—the knowledge gained from these experiments is indispensable, and it helps you fine-tune your route.
When you design your experiments, it’s essential to push yourself outside of your comfort zone and try new things to reveal new interests and passions. Have you always dreamed of taking an acting class or reading a book about psychedelic guiding but never made the time? Or do you long to express yourself through a new medium, such as writing, but never found the opportunity to pursue it? Don't be afraid to take risks and experiment with different activities or hobbies. Remember, this is a time to break free from limitations and labels and explore the full range of your potential and what excites you.
As you run each experiment, a goal is to become more in tune with your body and inner voice, following your attention, intuition, curiosity and energy. Does an action energize you or leave you depleted? Are you attracted to a specific action or repulsed by it? What’s guiding you—an inner knowing or the latest trend on social media? With enough reps, you’ll be able to trust your intuition, know what your heart longs for, follow your energy as a north star, and make decisions with more clarity and confidence.
Ultimately, prioritizing your explorations is critical if you're determined to make a change, especially among the myriad competing responsibilities such as your existing career and family. It’s imperative to set aside your current job and block dedicated time on your calendar. As a parent of two, I know that early mornings, nights and weekends are often the best time for these pursuits. This will ensure you're giving experiments the time and the attention they deserve. Remember that devoting just a few hours each week can accumulate to hundreds of hours annually, making a substantial impact on your quest.
There are endless experiments you can run and they all depend on your objectives and self-awareness. The goal of each is to discover what energizes you, who you are, and what’s possible.
Here are seven experiments you can conduct at any point in your transition journey.
1. Calendar & Energy Audits
A calendar audit is a process to understand how you spend your time over a period, typically a month or a quarter. It involves taking a close look at your schedule, noting how much time you devote to different activities, and identifying any patterns or habits that may be affecting your productivity or well-being. This is great for gaining insights into how you spend your time and identifying adjustments to more effectively align with your goals and priorities.
An energy audit is a similar process, but instead of focusing on time, it looks at how you allocate your mental and emotional energy throughout the day. An energy audit involves evaluating your energy levels throughout the day, identifying activities or situations that drain your energy, and finding ways to increase your energy and motivation.
With these experiments, you're testing what activities are energy giving, energy neutral and energy draining.
To learn more, here’s an essay I wrote, Aligning Your Calendar With What Matters Most, which provides a detailed process to reallocate your time based on your values and goals. Related, the Conscious Leadership Group (CLG) created an excellent Daily Energy Audit template, a simple yet effective process for tracking your energy.
2. Media
We're living in an incredible time where we have unprecedented access to information at our fingertips. With a simple click, you can access an abundance of research papers, books, essays, videos, and podcasts, making it easier than ever to learn, explore, and discover what truly energizes you.
Do you ever get that feeling where a certain book seems to be calling out to you? It might be time to take the plunge and finally make that purchase. Or maybe you've come across a captivating podcast episode that you saved for later. You might have even stumbled upon a thought-provoking essay on Substack that left you wanting more. And if you're not quite sure where to start, why not turn to your network and ask for recommendations? A simple question like, "If I want to learn more about X, where should I begin?" could lead you to discover some great resources.
When my wife first came up with the idea for her company, The Sill, she didn't write a business plan. Instead, she started by buying a book on plants that she had been thinking about for years, and craved more when we was finished reading it. And one of my clients, a recovering founder, is fascinated by the human genome and spends his evenings reading research papers about this emerging field after he puts his kids to bed. He often can’t sleep after because his mind is racing with new concepts and ideas. This is what you’re hoping for when you conduct media experiments.
The key is to follow your energy and curiosity, and immerse yourself in the topics that capture your attention. See how they resonate with you, and whether you're left wanting more or if you lose interest quickly. Pay attention to your response, and let it guide your next move.
3. Personal Conversations
Throughout the process, it’s important to seek the guidance and support of your partner, family, and trusted friends. While these conversations might be difficult to initiate for a variety of reasons, they are essential to surface and address any concerns or objections.
If you're worried about what people might think or say, consider reaching out to someone you trust to break the ice and test the waters. By voicing your desires out loud, you can experiment with how it feels and gain confidence in your decision. You can also discover how those closest you feel about a potential change, noting their worries and fears.
When you do talk to your loved ones, be honest and transparent about your longing for change and where you stand in the process. Explain the opportunities, challenges, and uncertainties that you are facing, and emphasize the importance of their support and encouragement. They might be able to offer a fresh perspective, help you identify blind spots, and offer encouragement when you need it most.
I've seen firsthand how valuable the input and support of family and friends can be during a transition. For example, one of my former clients, a former senior product leader at a public company, approached his wife early in his process to receive her blessing before he kicked off his transition. Similarly, I wouldn't have been able to successfully pivot my career without the early support of my wife, Eliza. Although it wasn't always easy, she was there every step of the way to provide advice and support when I doubted myself and didn't know which way to turn.
Instead of feeling pressured to include everyone at once, I recommend creating a small list and taking your time. As you move through the transition, you'll know who to include and when to involve them. Ultimately, the goal is to gather feedback and get their support.
4. Expert Interviews
As you gain more clarity on potential paths, it's helpful to speak with experts to gather insights and advice. These interviews can take many forms, ranging from informal conversations with acquaintances to formal research interviews with thought leaders.
These experiments help you understand the industry, identify the skills and knowledge necessary to succeed, and surface potential pitfalls and risks of the job. Most importantly, they help you prove or disprove whether the new career aligns with your values, personality, skills, experience, risk tolerance and financial needs.
Twitter, LinkedIn, and YouTube, as well as industry-specific podcasts, are excellent places to start. You can also leverage your network to find leads and get warm introductions. Look for people who are respected in their industry or community for their knowledge and experience. Ideally, they are one or two degrees separated from you. For instance, if you’re interested in climate, you could interview founders of climate companies, climate scientists, renewable energy experts, environmental advocates, policymakers, and leaders of climate-focused organizations.
In my own case, before I made any decisions, I interviewed six coaches who were three to five years ahead of me. These people were generous with their time, and helped me understand the certification process, daily challenges, and business models. These conversations literally saved me dozens of hours.
To get the most out of your interviews, it's crucial to come prepared with specific questions that will help you understand what it's like to be in their shoes. What path did you take? What's your day like? What advice would you give yourself when you were just starting? What training do you recommend? What’s your favorite part of the job? What’s the most difficult? The goal is to understand what it’s truly like in the profession and whether it aligns with your values, personality and experience.
5. Workshops & Courses
Courses are a powerful way to dive deeper into a particular topic or industry you’re excited about. They offer an opportunity to explore a potential career path, learn new skills, and acquire valuable knowledge. They can also provide the opportunity to build connections with like-minded individuals who can offer support, guidance, and advice.
In many cases, courses and workshops can be an affordable and low-risk way to learn new skills and explore new industries. Whether you prefer self-paced online courses or guided cohort-based programs, there are many options available depending on your interests and budget.
One of my former clients was passionate about climate tech, but felt she lacked the industry expertise, vernacular, and network to thrive. She enrolled in the OnDeck Climate Fellowship Program, which was a 10-week intensive cohort-based course that gave her what she needed to transition into climate.
Depending on your goals there are some excellent low-cost online options including Skillshare, Maven, Coursra and even YouTube. There are also many industry-specific programs and workshops available, such as Coaches Rising for coaching skills and Codeacademy for coding skills. Additionally, many universities and community colleges offer continuing education courses that are open to the public.
It’s important to know what you want to do your research and read reviews from past participants to ensure that it aligns with your goals and expectations. Most importantly, know before you enroll what hypothesis and questions you want this experiment to answer.
6. Moonlighting
Moonlighting is a strategy that involves taking on a second job or side gig while still working your full-time job. This can be an effective way to gain new skills, build experience, and explore new industries without sacrificing financial stability.
One of the biggest benefits of moonlighting is that it allows you to test the waters of a new career while still maintaining the security of your current job. This can be particularly important for those in midlife who may have financial responsibilities such as a mortgage or supporting a family. Over time, you can use this experience to transition into a full-time position in your chosen field or start your own business.
Moonlighting played a crucial role in my successful transition into coaching. During my time as a Partner at Primary, I maintained a select group of private clients who I coached after work hours. This experience allowed me to demonstrate that there was a genuine demand for my services, refine my pitch and value proposition, identify gaps in my skills, and validate my business model. Over the course of eighteen months, I proved to myself that I could successfully scale my coaching business and support my family.
Forms of moonlighting might include apprenticeships, internships or fellowships that teach you the profession without a full time commitment. The goal is to see whether you enjoy the nature of the role and it’s financially viable.
7. Prototypes
An MVP is a small-scale version that is designed to test assumptions, gather feedback from potential customers, and determine whether there is a demand for the product or service. These prototypes will provide valuable insights and help determine whether your skills and passion align with this potential path. This can be particularly important for those in midlife who may have financial responsibilities and need to ensure that their new venture is financially viable.
Creating an MVP can take many different forms, ranging from publishing five episodes of a podcast to launching a newsletter to running a Kickstarter to validate demand for an idea. For example, a recovering founder I’m close with just launched a college application service for high schoolers in under a month for just $2,000. Without much investment of time, energy and money, he’s gathering feedback and refining his product. Another client is launching a series of landing pages to test demand and conversion for a new NFT project.
When it comes to business prototyping, I often recommend Four Steps to the Epiphany by Steve Blank and Disciplined Entrepreneurship by Bill Aulet. While both offer valuable insights and guidance for entrepreneurs, the lessons contained within them can be applied to a wide range of industries and career paths. There’s also a wealth of information online about testing products and side hustles.
Moving Forward
Rick Rubin eloquently captures the essence of unfolding in his reflection in The Creative Act: A Way of Being:
“We tend to think what we're making is the most important thing in our lives and that it's going to define us for all eternity. Consider moving forward with the more accurate point of view that it's a small work, a beginning. The mission is to complete the project so you can move on to the next. That next one is a stepping stone to the following work. And so it continues in productive rhythm for the entirety of your creative life.”
Remember that every experiment you conduct is an opportunity for a new beginning, a stepping stone that leads to the next one. Change and transition is a creative process, and experiments allow us to play around and explore new possibilities. In fact, many great discoveries and inventions were made by scientists who were just playing around, experimenting without any pressure to figure everything out.
As you embark on your journey of experimentation and your path begins to unfold, it’s important to incorporate practices such as meditation, journaling and visualization into your routine. These practices help you reflect on what you observe, extract valuable insights, and potentially identify the next step forward. Additionally, by regularly engaging in these practices, you can develop a deeper sense of self-awareness, which is essential for making intentional and informed decisions about your life.
Approach this journey as a fun adventure rather than a quest to find the perfect career that’s going to define you for eternity. Instead of putting pressure on yourself to achieve a specific outcome, embrace the path that you’re on as an unfolding journey that will eventually uncover your unique gifts, values, passions, and purpose. Allow yourself to be open to new experiences and perspectives, and embrace the process of self-discovery that comes with each experiment. By doing so, you can begin to unlock a new world of possibilities and begin to create a career that is not only fulfilling but also aligned with who you are and what energizes you.
Transitioning to a new career won't happen overnight, and it's important to acknowledge and accept that it will take time. Just this week, I had a conversation with an entrepreneur who left his company two years ago after taking it public and he’s still searching for his next calling. In my case, it took nearly five years from the moment I resigned from RRE Ventures to fully embracing my new identity and life as a coach and writer. Bruce Feiler, author of Life Is In The Transitions, notes that the average life transition lasts three to five years. So, be prepared to invest time and energy in the process, and don't expect immediate results.
And you might realize after running a series of experiments that you’re unwilling to change careers because your current job pays the bills, provides health insurance, and creates financial stability. I can’t think of a more important calling than providing a good life for your family.
Embarking on a career transition in midlife is not easy, and you're bound to face setbacks and obstacles. It will likely be one of the more difficult and emotional experiences of your life, but it will also be one of the most rewarding and enriching.
As you navigate each experiment just remember to trust the process and what unfolds. Good luck!
Steve- thank you so much, this was exactly what I needed to hear right now as I transition from my “safe” job of 8 years and decide what’s next. I love this concept: “Approach this journey as a fun adventure rather than a quest to find the perfect career that’s going to define you for eternity. Instead of putting pressure on yourself to achieve a specific outcome, embrace the path that you’re on as an unfolding journey that will eventually uncover your unique gifts, values, passions, and purpose. “ I already have some experiments going (I am a scientist so this really resonates!), and I’m working on cultivating a sense of excitement and curiosity rather than fear about what’s next. I am also trying to be ok with not knowing the full answer to “what do you love to do?” Thanks again!
Loved it. Thanks for putting out it.