Free Advice: How Coaching Found Me

Since 2019, I’ve coached dozens of founders and executives, and I’ve kicked off each of those relationships with a little white lie.?

A new client will inevitably ask, ‘Why did you become a coach?’, to which I respond with something like: ‘I spent 15 years as a consultant, investor, and entrepreneur, and I realized what I most loved about those experiences was developing my teams personally and professionally. So, I sold my businesses to focus on just doing that.’ It’s a neat story – a bridge between chaos and meaning – but it’s far from the whole truth.

The truth started on a cloudy Sunday in 2016 at Dolores Park. Dan Tuttle and I, armed with folding chairs and an orange ‘Free Advice’ sign, set up shop next to the tennis courts at 18th and Dolores. ‘Free advice! Will talk about anything!’ we hollered at passersby. Most ignored us, keeping their gaze on their dog or the cooler of beer they were schlepping into the park. Some yelled back obscenities. Others were polite. ‘No thanks,’ like we were selling Thin Mints. Eventually, people began to wade over. A common opening:

- ‘What are you giving advice on?’

- ‘Whatever’s on your mind.’

- ‘What makes you qualified to do this?’

- ‘We’re not. We’re just wanting to talk to people and help however we can.’

- ‘How much are you charging?’

- ‘Nothing.’

- ‘Weird.’

From the 20-ish people we talked to, I most clearly remember the 18yro woman visiting from Austin. The upcoming election would be her first as a participant, and she didn’t know who to vote for. Her eyes welled with tears as she relayed her pros and cons of Hillary vs. Trump. This mattered to her. There were many opportunities to share that I was a Hillary supporter, to make an argument, to sway her like a canvasser would. But that tack didn’t feel right. I sensed what she was and wasn’t open to hearing from me. I remember asking her to describe her confusion, her fears, what issues were important to her. She left the conversation feeling calmer, and with some next steps around self-reflection and research. I left the conversation feeling both surprised at how well it went, and clear that she didn’t actually want advice.

More broadly, I remember how much I enjoyed learning about strangers’ lives. The pangs of fear as people approached -- a young fear (‘are they gonna laugh at me?’). I remember feeling exceedingly present. I wanted more.

What I don’t remember is why Dan and I decided to do Free Advice in the first place. It was part social experiment, part something fun to do. In hindsight, I was looking for meaning. Professionally, 2016 was the most hectic year of my life. I was running two businesses, starting a third, and had just gone through a messy business partner split. Amidst it all, I felt unfulfilled, like I was going through the motions. Also, I went through a breakup that summer. Perhaps sitting with other people’s pain was a way for me to move through -- and connect with -- my own

We returned to Dolores Park in early September. I had a 20min session with a sweet, earnest guy in his late-20s – worked in tech, fleece vest – who was just offered a promotion he’d wanted and now wasn’t so sure. He needed to give his boss an answer. I asked him about his role, the company, the comp, his future plans (‘business school…maybe?’). Taking the promotion made all the sense in the world, but his heart wasn’t in it. I asked him what would happen if he turned it down. ‘I’d probably quit and travel for 6 months.’ We explored further. The promotion – staying the track – was how he’d lived his entire life up to that point. Throwing it all away to travel represented freedom, a reclaiming of something personal.

The following Sunday, he strolled past as Dan and I were both engaged in 1vs1s. ‘Hey – Free Advice guy. Thanks again. I gave my two weeks! Got a ticket to Argentina!’ I remember feeling proud that I played even a small role in helping him make such a big decision. I also felt envious of his boldness.

Dan and I kept showing up with our orange sign one or two Sundays a month. It wasn’t always easy. Most passersby still ignored us or yelled obscenities. Sometimes we’d have no takers for hours at a time (‘Uhmm…let’s just stay until we have one more good one.’) But we’d also hear people elbow their friends from the sidewalk, ‘Look, it’s the Free Advice guys.’ And sometimes it wasn’t free. One lady was so appreciative of our conversation, she returned with an offering of a Bi-Rite ice cream cone.

I can still picture some of them. The guy heading home to Indiana for Thanksgiving and wondering if he should tell his family he was gay. The Rabbi torn on choosing a theme for his upcoming Yom Kippur sermon. The mid-30s entrepreneur who just closed a seed round and no longer thought his business model made sense. The terrified Mexican woman. Her husband was physically abusive, and she didn’t know what to do given that she was undocumented. The most common question Dan and I received over those two years? ‘I’m being evicted -- what should I do?’ The Zeitgeist of pre-Covid San Francisco.

I was learning something profound: people didn’t need advice—they needed clarity. Beneath their questions about family or housemates or career moves was a deeper yearning to align with what truly mattered to them. My job wasn’t to offer solutions; it was to help them unearth their own.

The Free Advice branding belied the coaching we were actually doing. The conversations weren’t about answers—they were about energy. When we follow what makes us feel alive, we find alignment. James Hollis, the Jungian psychoanalyst, frames it well: at life’s crossroads, we should ask ourselves, ‘Does this choice make me larger or smaller?’

Our Sunday visits to Dolores Park dwindled through 2018. Dan got married, I moved to Oakland. I sat, talking in circles in my therapist’s office. I didn’t want to be where I was but couldn’t see a way out. She asked, ‘When do you feel most alive?’ I thought to myself for what felt like a while, staring past her plants and out the window onto Valencia Street. ‘When I’m doing Free Advice,’ I said. She responded, ‘So why don’t you just do that?’?

I hired my own coach. I signed up for a coaching training and started coaching friends for free. I eventually upped my fee to $75 a session. I made a website. I held my breath as I changed my LinkedIn headline.?

Today, I coach clients and teach coaching and facilitation to Stanford MBA students. If you were a fly on the wall of a given class, you’d likely hear me talk about ‘following the energy’. Good coaching is about following the energy, wherever it’s leading. Often, so is life. Authentic living isn’t about grand gestures; it’s about listening deeply to ourselves and overcoming the fears and inertia that block our path.

We all walk through life feeling misaligned, sometimes subtly, sometimes starkly. But when we align with what makes us feel most alive, we find clarity, purpose, and truth. Simple, but not easy.?

It’s been more than eight years since that first ‘Free Advice’ session at Dolores Park. What I see now is that helping others follow their energy was the first step in following my own.