My Fall Mastermind is Open for Applications

My Mastermind & Mentoring program will return this Fall. You must apply by August 18th to be considered for the early decision deadline. The latest possible day to apply is September 5th if you’d like to be in the Fall cohort.

Apply by August 18th for the early decision deadline.

We’ll work together from Sept 18th —January 12th, 2018.  The program is a little more than 3 months long and requires a dedication to expanding yourself, your business, and your mind. It costs $3500.00

The pilot program of the virtual mastermind launched in the Fall of 2016, with a group of incredible people, including a social impact CEO, a PhD poet, an independent architect, a global nomad, a google software engineer, and more. To date, I’ve hosted five different groups of ambitious, extraordinary people: authors, technologists, startup co-founders, and young entrepreneurs in the process of personal transformation.

If you’re at a time in your life when dedicated focus and an outside advisory board will help you level up to the next level in your personal and professional life, I strongly encourage you to apply.

Fill our your application for the Mastermind here.

Early decision applications are due by August 18th, and I’ll be begin interviewing candidates August 22nd. The very last deadline to apply is September 5th. 

Here’s what a few people have written and said about the program:

“My biggest “A-ha” moment was that we need others. None of us can do it alone. It made me realize how much of a bubble I’ve been living in. I knew the Mastermind was what I needed, but I had no idea how fulfilling it would be.” — Shannon Callarman, Content Director at Red Caffeine Marketing & Technology

“This mastermind is a group of people with diverse, dynamic skills and experiences who come together with a shared investment in digging in deep to goals, ideas and ways to be even better at what we do. It is a structured with workshops, one-on-ones, journaling, calls, meet-ups, rituals and exercises that will help you think bigger, inspire you to reach out for help and consider new ways of being and doing that are YOU x 1000.”— Jessica Ashley, Content Strategist and Creator, Founder of Single Mom Nation

“If you can come to the group with even a vague description of what you’re struggling with or where you want to get to, the group will help you get to the root of your goals and break down that problem into tangible pieces. Once made conscious, you can then work systematically to tackle these various pieces and make serious progress towards achieving your goals.”— Patrick, Robotics and Engineering Consultant

Who is it for?

“I loved the diversity of people who shared the same values of motivation, growth and learning. It totally exceeded my expectations! This is a structured Mastermind with the opportunity to meet other high-quality, motivated people, dig deep into your questions via deep dives and make progress on your goals.” — Diana Jaunzeikare, Software Engineer, Google

“With two very young kids, I came into the Mastermind knowing that spending time with family was a top priority for me, but uncertain how to balance this desire with my love for tech startups and being part of big things. The biggest “aha” moment occurred when I took an objective look at my schedule and figured out how much I can work without sacrificing other aspects of my life. Given this framework of thoughts and constraints, I could then look to design a career that I’m passionate with inherent firewalls to protect against overwork.” — Patrick, Robotics and Engineering Consultant

“The experience of going through the mastermind with you and our crew was incredible. It left me feeling inspired, supported, poised, and empowered to take action to make my dream of running my own business a reality! I learned concrete tools and ideas from you and my peers in the group and felt truly held and heard in all of our interactions. Thank you for creating this space for our group to gather.” — Gretchen, Senior Planner, San Francisco

“The Mastermind is perfect for highly driven individuals looking to build a trustworthy and dependable tribe to help them move forward. It’s for the type of person who not only is willing to ask for help, but also willing to show up and be there for others 100%. The Mastermind is perfect for both introverts and extroverts — the only requirement is deep curiosity.”— Shannon Callarman, Content Director at Red Caffeine Marketing & Technology

“This mastermind is perfect for seekers, for people who work for themselves or have their own businesses, or who feel called to break away from the pack. It is perfect for those who have personal or professional ideas that feel exciting but overwhelming, or who crave community and accountability, who need some structure and support in making something amazing come to life.” — Jessica Ashley, Content Strategist and Creator, Founder of Single Mom Nation

Not sure yet but curious about what it is?

I have a series of emails explaining how it works. Get the free Mastermind email series here. But don’t forget to apply if you’re genuinely interested in the program.

Do You Have Your Own Personal Board of Advisors?

I didn’t realize I needed a personal board of advisors until things got pretty rough.

I was stuck, trying to do everything myself, trying to learn faster and stay up later to make it work.

Then, one summer when I was running too many programs all at once, I finally caved and hired teaching assistants for my writing workshops. I can’t believe I didn’t do that sooner.

One of my early students, Emma, reached out and said she wanted to help with a teaching assistant position I had. She was incredible. She, in fact, was the one that taught me about the need for a “personal advisory board.” It became a phrase that stuck with me.

(If you’ve been following my work since the beginning, you might remember when I taught my first 30-person digital writing workshops. I’m still following and in touch with so many of the writers from those groups!)

Now if you’re running a company or a startup, of course you’d invite the best of the best to be on your Advisory Board to help you think through sticky puzzles and challenge moments.

Why not have the same thing, but for your own life?

Hence, the personal advisory board: your crew of people that you call on for brainstorming, business advice, and sound listening.

In this post, I want to tell you about ways you can build your own circle of trusted friends and colleagues, why joining or starting a mastermind is so important, and why people are so foundational to both your personal and business health.


In your own life, what work are you doing to build your own personal board of advisors?

After working together with Emma for several cycles of the writer’s workshop, I remember the phone call where we giggled and said, “look, we work together, but we’re also clearly friends. This has become something even better.”

Fast forward several years, many trips, a retreat in Tahoe, randomly meeting in the same airport in small-town Kentucky, and hundreds of messages later.

One night, I’m sitting in the bath, taking a soak, trying to relax after a long day with the family and the business. It’s one way I try to get my head to turn off. I’m reading, of course, her recently published book. She’d sent me a bound copy of her poetry collection. At the end of the book is an inscription and a note:

“SKP — you chair my personal board of advisors.” 

It’s moments like these that make me cry.

We’d spent so much time in the ring, figuring out, discussing, learning, philosophizing. Wondering about what to do in the stuck moments, and how to untangle ourselves from the insatiable urge to try to do everything.


Having people to call on is one of the soundest investments you can make in your life.

Whose advisory board do you sit on? Whose life are you invested in? Who have you invited into your life to chair your own advisory board?

Building your own mentorship circle, or trusted peers, can be a challenge to do. Whose feedback do you trust? Who do you invite in? Not everyone’s feedback is equal. In fact, unsolicited feedback at the wrong time can really sink a project or make you question something when it’s not the right time to be questioning. Developing a circle you trust is an art form.

One of the things I teach in the Mastermind is how to build a circle you can trust. It’s not something that happens by accident.

Inviting people into your personal and professional life takes dedication and work. But you don’t have to reinvent the wheel. In the Mastermind, I teach:

  • How to create a container and set an intention for a group.
  • How to structure your time together with your group.
  • Key methods to listen effectively and listen well—asking deep questions that provide additional insight.
  • Why most “advice” is not only useful, but can be harmful to the process (and what to do instead).

By the end of the Mastermind, you can take everything you’ve learned and apply it across your life—I have had several people tell me afterwards that “they run Deep Dives for their lives,” using them in relationships, partnerships, and business to great success.

It is a lot of work to create a personal board of advisors, but, if you want to — you can build one on your own. You can also selectively join one that already exists, and adopt the structure for your own long after the program ends.

The Mastermind I run takes a ton of the organizational and logistical work out of it. I’m your facilitator, your guide, your organizer, your accountability buddy, your mentor. I make the structure so you can find resonance and meaning within it. The edges of this framework help to sharpen you and accelerate your work.

Now, I don’t have a patent on creating masterminds — so if this is something you need, you are more than capable of building it yourself and figuring out how to make it happen in your life.

Bring together a group of 4-6 dedicated people to meet monthly. Commit to journeying together and asking insightful questions. Put each other in the “hot seat,” and listen to someone explain a sticky challenge they have. Do it for at least six months.

Apply to join my Mastermind.


8 tips to building your own personal board of advisors:

  1. Take it seriously. Create a one-page manifesto or description of what you’re doing and why you’re doing it. Invite people in and ask them if they want something like this in their life. (Heck, you can forward this email and say to your friends, “want to build something like this?”).
  2. Keep the group small enough to manage, but with enough voices to get multiple opinions when you need it. 4-5 is a great size, but it can range anywhere from 3 to 10.
  3. Decide how often you’ll show up for each other and what that will look like. Monthly? By email? By text?
  4. Decide who is doing the organizing. Planning, organizing, and logistics take a lot of work. Consider rotating the cap every quarter so that everyone contributes. In most of the Masterminds I’ve been in, usually it works best if one person is the facilitator.
  5. Set intentions and a time frame: for example, you might do 6 total meetings over the course of 6 months and evaluate what happens.
  6. “Try on” a structure for a few months, and then step back and evaluate what works.
  7. Give it time. Great things take time. Adjust what isn’t working and fix it to make it better.
  8. Call it if it’s not working. Sometimes it’s not the right group or the right mix of people. If you start one and it doesn’t work, mix it up a bit and try again. Be straightforward and let people know your intention to end the group or change it.

Invest in meeting new people on a regular basis: 3 strategies

There are several ways to invest in meeting new people:

  • Reach out and write to people you admire. Follow their blogs, send them an encouraging note, or chime in on Twitter. I’ve met lots of people on Twitter, including one of my best friends (and business confidants)
  • Go to conferences or events where the people you want to hang out with spend time. One conference ticket might seem pricey, until you realize that you can meet a dozen people all at once and form new connections and ongoing conversations with other brilliant people.
  • Create meet-ups or projects where you can invite people to participate. Start your own group and invite people you admire to join you! It can be a small one-time meetup, a virtual hangout, or a more dedicated monthly circle that meets on a regular basis.

Will you spend all your time on work, or on building connections with people that matter?

The world of work is changing faster than ever.

Jobs that were stable for decades are disappearing, and skills we didn’t know about 20 years ago are the most important thing you need to know today. Skills we didn’t know about two years ago are needed today. There’s a lot of uncertainty about what’s going to change again in the next five, ten, and fifteen years.

One thing that will always matter is who you’re connected to. Our strong ties and our weak ties are some of the greatest predictors of our future success.

Yet time and time again I see people investing in courses or materials, but not in connections with other people.

What’s the value of a great connection in your life? Someone who connects you to new people, ideas, thoughts, and jobs? What small effort would it take to formalize the connections you have with other people, to meet regularly?

What could your life look like with your own Personal Board of Advisors?

A book or a course might run you a couple hundred dollars. A new set of friends… is there any way to put a price on that?

Inside My Business Philosophies: What’s Worth Your Time, Attention, and Money?

I’m not in the business of selling quick fixes.

In fact, a lot of the work I do is slow and boring. I can whip up content marketing like the best of them, but I’m most interested in what behavior change approaches actually work, and what really helps us in our business and personal lives.

There are so many programs and courses and marketers out there selling you the “top ten easy ways to do things.”

The perpetuation of the “how” generation is desperate for advice on how to do something. Most of this is just noise. A lot of it is smoke and mirrors. Raise your hand if you’re tired of it — I know I’m tired of it.

Because how do you know how to figure out what kind of life you want to live? 

And how do you set up the right structures for you in your own unique business and life?

I’m not sure the internet can give us those answers.

What’s more important is identifying and knowing your own universal business and life principles.

Today, I want to share with you some of my core principles for my business and why they matter to me.

In my work over the last decade, I’ve learned a few truths that have been universal for me, and they’re what create the foundation for my business and the decisions I make.

When I share them with people I work with, friends, or even recently, the coffee shop barista near my new house, I get smiles and nods. These are my people.

These are the values and beliefs I hold behind the work I build. Everything I build, everything I make, the things I think about — these are what’s guiding my decision-making. When I make a new course, it’s usually in an effort to solve one of these problems.


Belief #1 — A lot of people are lonely, especially in today’s hyper-connected world.


We are more connected than ever before, and yet we’re more separated and disjointed. Social media is rewiring our brains. We have a lot of loose connections but we have lost the depth of our close ties. We live in very separated houses, with individual bedrooms, silo’ed into our own automobiles, staring down into our cell phones.

We’re so separated that we don’t know how to approach people or date people without the help of apps.

Loneliness is a big, pervasive problem.

That’s why what I’m working on now in my business isn’t a scaleable one-off, me-to-you video program. (You can take those, of course — and watch my writer’s workshop, etc). But it’s more than that.

I want to build places for people to come together in community.

Specifically, I want to create small micro-groups of people that can become friends for life. I am invested in building ecosystems of support through connecting highly talented, creative, independent people together.


Belief #2 — Discomfort, guilt, and feelings of uncertainty aren’t markers of failure.


Modern education has trained us to be obedient, subservient, and to pass tests. How has that served us? We seek comfort and familiarity rather than growth and challenges.

But discomfort, guilt, and uncertainty aren’t bad. It’s not a sign that you’re on the wrong path. It’s actually a deep measure of growth and learning.

If you’re ever confused, uncertain, or questioning: these aren’t markers of failure. These are markers of growth and learning.

We’re not on a quest for certainty and expertise. The gurus in my life are still students, always students. We’re always learning.

I learn so much from each person that joins my mastermind. And they tell me they learn so much from me. To put yourself into a place of learning is to allow yourself to grow. Stagnation is one step before depression.

Learning and growth require periods of uncertainty and discomfort. It’s part of the equation.


Belief #3 — We’re swimming in information and yet unable to speak.


So often we’re told and taught that if we just learn a little bit more, then we’ll be okay. That if you just read a little more, learn a little more, or watch a little more, then you’ll have the answers. Then everything will work.

Has that actually worked in your life? Once you finish that video series or that class, did you feel like you suddenly had all the answers?

No! It doesn’t work like that. Each time you learn more, you unpack more… that you don’t know, or that you want to know.

In my work, I encourage people to use their voices.

I don’t want to be sharing information to a silent room. I want to be in the room with you, learning from you, hearing what you have to say, seeing your work evolve and grow over time. Using your voice, through whatever medium is best for you, is part of the work of being human.


Belief #4 The things worth investing in take time and dedication.


In an instantaneous world, it can feel antagonizing to work on long-term projects. The quick hit of a social media “like” or an open to your email feels good. But when you fast forward a little bit, and you add up what matters, will having 200,000 views on your YouTube channel translate into the life you want?

In my own life, I’m in pursuit of smaller, richer communities.

I want to add vibrancy and resonance to real human lives by creating a place to invest deeply in ourselves and in each other.

The Mastermind project I’m working on now is something I’ve been wanting to make for a long time. I want to figure out how to bring people together, connect them, and unpack what it means to live a complex, rich, devoted life. What does it mean to have devoted time to yourself and your dreams?


So, what does this all add up to?

Over the next 14 weeks, you can check Facebook a little more.

You can attempt to read all of your emails. (Yes, even I still try to do that, even though I know it’s not going to get me what I want.) You can even buy a bunch of classes. But what’s going to really add up to change in your life?

The Mastermind that I’m creating is about the following principles:

  • We do better work when we’re connected deeply in community.
  • Using our voices is an art, built on principles of deep listening and engagement.
  • The things that matter can take a long time, and require dedication and commitment, even through periods of uncertainty.
  • Uncertainty and frustration are markers of growth, not failure — and having a community around us to witness our growth and struggle can make all the difference.
  • Building places for people to come together in community
  • Deep work, built on principles of deep listening and engagement (I teach you how to use deep listening in your work).

In the Mastermind (if you do decide to apply to join), we take the time to look at why you do what you do.

There’s an exercise we do called “finding your ways of being” for how you want to show up in the world. We look at what mantras and principles you want to live by. We examine what works and what doesn’t work, and why there might be differences.

It is a rich place of growth, depth, and connection, and it takes us time to go through the process.

These aren’t things that I can sell in an e-book or a course.

I’m sharing this because of how important and vital I think this work is. I can’t scale it because there is so much 1:1 work involved.

This blog (and the free email info series all about my Mastermind) is my attempt to share what it is I’m building and why I’m building it. If you do decide to apply, I read every single application, and get on the phone with as many people as I possibly can.

When you take the time to figure out your “why” in your own business and personal life, it helps you shift the way you see your work in the world.

It means you meet the right people, and choose projects that matter. It’s helped me in countless ways: setting up boundaries between what I’ll say yes to and what I decline. Helping me make decisions and set up structures for success.

If this post resonated with you, if you find yourself nodding along, if what I’m talking about makes sense, then I’d love for you to apply to the mastermind. It’s a small group of people, and I think very carefully about who ends up joining. But I can’t add you to the group if you don’t apply. We start on March 6th, so I’m finalizing interviews through the rest of this week, looking for one or two more faces I haven’t met yet to possibly add to the mix.

Here’s the link to apply if you haven’t already — Apply today.