Find a Sustainable Pace

I help you find a sustainable pace by revealing the choices that keep you stuck—and cultivating the courage to try something different. Most founders set an unsustainable pace because they believe they have no choice! And it works, for a while. But if you want to build a business that lasts, you’ve got to start choosing carefully how you invest your limited time and energy. Not just to prevent burnout, but to make sure you’re doing the work that matters most.

We identify these unsustainable choices by noticing how they make you feel. The frustration of an important truth you’ve chosen not to name out loud. The stress and exhaustion of a difficult conversation you’ve chosen to force or avoid. The anxiety of not being sure which choice is right—when time and money are quickly running out.

But often we believe we have no choice. We can’t name the unspoken truth out loud: it would only make things worse. We must avoid difficult conversations to keep the peace. Or repeat them over and over—even when their message isn’t landing. Of course we have to be sure before we make a hard call.

I help you see how these beliefs keep you stuck—and prove them wrong. Because we always have a choice. We just don’t always have the courage to embrace it! We find a sustainable pace by cultivating the courage to explore different choices. With practice, courageous choices that once felt impossible can become routine. 

Reignite Your Love for Work

I reignite your love for the work by reorienting what you do around a purpose that matters. Why does loving your work matter? Sustainable motivation! Often we open a new chapter in our careers energized by its possibilities for learning, growth, and impact. That sense of purpose is exactly what gives great leaders the longevity to build businesses that last. Time flies when you’re having fun!

But then we run into challenges that don’t feel so fun. We get scared of failure, and struggle to make courageous choices. Perhaps you’ve noticed that startups aren’t all sunshine and rainbows—they’re hard! And not everyone has a coach to help them see their unproductive patterns. That’s why many startup leaders spend their days living and working in fear: trying desperately not to fail instead of trying to succeed. Doesn’t sound like work you’d fall in love with, does it?

That’s why loving your work matters so much. Not just to have more fun at the office, though that helps! On a multi-year startup journey you’ll face hundreds or thousands of tough decisions. Without love for your work, those accumulated stressors can quickly lead to stress and burnout. Loving your work gives you the fuel to make courageous choices every day. Not because those choices are easy, but because they matter so much to you. It would be an honor to help you reignite that love in your work.

Build a Business that Lasts

I challenge you to build a business that lasts by mastering your craft through continuous experimentation. So let’s say you’ve cultivated the courage to make more sustainable choices in your leadership. And you love your work enough to sustain that courage over the long term. Congratulations! But courage alone won’t build a business that lasts. Courage will open up new choices for you, but not necessarily the wisdom to know which to choose. 

That wisdom comes with practice. Not just making one courageous choice, but many of them over days, weeks, and months. Noticing which choices produce results, and which fizzle out. Which choices build trust with others, and which erode it. Which choices feel right to you no matter the outcome, and which choices feel wrong even when they look like success. I’ll help you build your own leadership wisdom through clear-eyed reflection on the results of those courageous choices.

Building a sustainable business means continuously honing your craft as you, your business, and the market itself continue to evolve. Love for the work provides motivation, but mastery comes through perpetual experimentation: expanding your leadership range and proving what works for you. I’ll help you develop your own unique leadership style through regular experiments in the real world. That’s what it takes to build a business that lasts and do the best work of your life.

How does it work?

Outcomes

  1. I help you find a sustainable pace by revealing the choices that keep you stuck.
  2. I reignite your love for the work by reorienting what you do around a purpose that matters. 
  3. I challenge you to build a business that lasts by mastering your craft through continuous experimentation.

Skills

  • Master hard conversations: tough feedback, conflict, crisis management
  • Build a high performance team: hiring, delegating, creating accountability, developing people
  • Make decisions under uncertainty: act without waiting to be sure
  • Protect your time for what matters: reserve your energy for what only you can do
  • Manage stress and prevent burnout: even under the most difficult circumstances
  • Build a distinct, opinionated, intentional culture: not one that happened by accident

Logistics

Typically I meet with each client 2-4 times a month for an hour. We can connect via Zoom, phone, or in person in San Francisco. I even offer walking sessions in your local park or along the Embarcadero. I charge a flat monthly rate that includes:

  • Unlimited 1:1 coaching sessions (at least 2x monthly)
  • Limited small group coaching sessions
  • Written reflections on each session via email
  • Unlimited correspondence via email and text
  • Weekly accountability check-ins via email
  • Typically paid by the company
What topics do you coach?

Over a decade of coaching startup leaders, I’ve covered pretty much any topic you could imagine:

  • Operational: product, design, engineering, data, marketing, sales, manufacturing, legal, etc.
  • Organizational: hiring, org design, delegation, communication, feedback, etc.
  • Personal: imposter’s syndrome, stress, time management, anger, anxiety, etc.
  • Interpersonal: poor relationships with management, peers, reports, board, investors, family, etc.
  • Strategic: fundraising, acquisitions, layoffs, culture change, exit strategy, etc.

Any topic is 100% welcome! I’m happy to share best practices, but you can get those from your favorite AI chatbot. What’s hard is understanding what’s holding you back from adopting those best practices—and that’s where I can really help. I take the time to understand you deeply, so I can offer you personal insights instead of generic best practices.

What’s a typical coaching engagement like?
  • Often the first few months focus on resolving any urgent recurring issues such as interpersonal conflict or stress/burnout. Usually there’s a clear pattern of unsustainable choices rooted in fears you’ve been avoiding. By finding the courage to face those fears, we break the pattern and empower you to begin finding a sustainable pace.
  • Once we’ve identified your 2-3 key unsustainable choices, we start experimenting with new courageous choices instead. With your fears no longer your central motivation, we take the opportunity to reconnect with your sense of purpose and reignite your love for work. With regular experiments we gradually find the pace that’s sustainable for you and prove empirically how you can deliver effective results.
  • With enough practice, courageous choices that once seemed impossible become the new normal. Having long since identified a sustainable pace for work they love, my long term clients focus on practicing their skills to develop their wisdom and achieve mastery. Instead of avoiding their fears, they relish the fun and challenge of gracefully embracing each new challenge as they arise.
What results do your clients see?
  • After each session, clients often mention feeling calmer and clear about their plan to move forward. 
  • After a few months, clients usually have a clear understanding of the patterns of risk they’ve been avoiding and how they stand in the way of their ambitions.
  • After six months or a year, clients usually report feeling less stressed overall, and more able to lead in ways they’re proud of even under difficult circumstances. 
  • After a couple years, clients typically are achieving their bold ambitions, know very well how to handle most challenges, and are having fun optimizing how they lead to best express their highest intentions.
How do I choose the right coach for me?
  • Trust your gut! I recommend focusing on finding a good fit in both budget and interpersonal chemistry. 
  • In terms of budget, the company should pay for your coaching. Investors see exactly how many companies fail due to leadership, so they’re typically very supportive of coaching at the executive level. Great coaching is expensive but worthwhile, especially for high leverage leadership roles. 
  • Chemistry is harder to predict, you really have to try out coaching together to see how it feels. If you feel inspired by the idea of doing the best work of your life at a sustainable pace then I’ll bet we’ll get along just fine. 
  • Fortunately I offer a free one hour sample session to CEOs, founders, and executives at startups, so please get in touch and we can discuss. After a sample session it’s almost always clear whether we should continue working together.

Curious to learn more? Let’s get started.

Contact me