Category Archives: Crafting Your Career

In the new world of work, you have to take responsibility for designing the arc of your own body of work. What will your career look like? What projects will you be a part of? In crafting your career, what’s most important to you about what you do?

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?

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