How to Sell Yourself – A Workshop
I taught a 100+ person workshop this week for Sidebar, a community of senior leaders in tech. Today, I thought I’d share the session – along with a write-up about it.
You can watch the full workshop here:
Robin’s Pumpkin Patch
My first business – if it can be called that – was at 5 years old and entirely attributable to my father. My dad took me outside to a patch of recently cleared ground and had me plant pumpkin seeds.
All summer long, I was responsible for watering and weeding these growing pumpkin plants. Then, when the plants grew pumpkins, my dad had me place them around a little stand with a sign that read “Robin’s Pumpkin Patch.”
Over the next month, some friends and I would dress up in scarecrow costumes – head completely covered, hay sticking out of our gloves and boots – and flag down passing cars.
There was no skin showing, so that when cars would come by and we’d start moving, they’d try to figure out where the motion sensor was.
If one of my friends was dressed up in the scarecrow costume, I’d run out after the car, say “I’m Robin! Welcome to Robin’s Pumpkins Patch. Would you like to buy your Halloween pumpkins today?”
When I think of that business, the only thing I can think of to describe it is “joyful persistence.” After I realized that I could sell these pumpkins I’d grown, I was delighted.
It wasn’t self-promotion; it was adorable. I was being of service by being authentically, enthusiastically myself.
Exercise:
What’s your authentic attitude of self-promotion?
Mine is enthusiasm. What’s yours?
Getting Fired as a Personal Trainer
One of my first jobs out of college was as a personal trailer. Anyone who has ever been associated with gyms knows that gym culture is all about selling memberships and personal training sessions. I started personal training because I liked fitness, but found that I had no clients.
Within about two weeks, the owner of the gym sat me down and said, “You’ve got no clients. We’re spending money on you. Either have some clients by the end of the week, or you’re fired.”
I froze.
I tried to walk the floor. I tried to talk to people. But I had a needy quality – desperate, afraid of getting fired. So, unsurprisingly, I got fired.
We’ve all experienced selling ourselves from a place of need – asking for a raise, asking for a date, pitching work – when it feels gross. It felt gross to me, and it feels gross when someone does it to me.
What’s funny is that a couple of weeks later, I was walking down Valencia Street in San Francisco and saw a guy leaning against a wall, holding his back in pain.
I walked up to him and said, “You look like you’re in pain. I’m a former athlete. I’ve had a back injury. I might be able to help. What’s going on?”
It turned out he needed help. He wanted support. He wanted personal training.
The next client I met was in the locker room of the UCSF swimming pool. He asked what I did, and I said, “I’m a personal trainer.” He said, “Oh, I’m looking for a personal trainer. Tell me about your work.”
The connection came from a genuine desire to connect, not to sell.
I learned that there are two versions of self-promotion. One comes from delight, enthusiasm, and service. The other comes from need.
When I promote myself from need, I freeze. When I show up from service, things work.
Exercise:
When’s one time you felt slimy? What were you doing?
When’s one time you felt good? What were you doing differently?
Stakeholders at Robin’s Cafe
In 2016, I opened a café and restaurant in the Mission District of San Francisco.
I had no restaurant experience. Other than bussing tables in college, I didn’t know what I was doing. I opened it in three weeks.
It’s called Robin’s Cafe, and it’s still around today, though I don’t own it anymore.
At the time, I lived in the neighborhood. I’m a self-taught dancer, and the café was housed inside ODC – a 40-year-old nonprofit dance center that owns real estate in the neighborhood.
The corner where the café opened was rough. There was a parking lot across the street with prostitution and drugs. Three years later, when I sold the café, that same corner was a kid’s playground.
The café worked because I knew exactly who I was serving.
Employees – I deliberately created Robin’s Cafe as a great place to work.
Investors – I borrowed forty thousand dollars from family and friends. These people made the business possible. They were literally invested in its success.
Landlord – ODC owned the building. If the café failed, that reflected poorly on them. If it succeeded, it made them look good. They wanted a place where dancers, parents, instructors, and neighbors could gather.
Customers – Tech workers moving into the neighborhood. Twelve-year-olds coming for dance class. Parents buying coffee. Customers mattered—but they weren’t the only people who mattered.
Me – Financially, I needed to earn something. Emotionally, I needed to care. If I wasn’t interested, excited, or learning, I wouldn’t keep going.
When things got hard – we had break-ins, flooding, competition, city permitting, and a homeless encampment down the street – what kept me going was knowing who I was in service to.
A successful business serves many people at once. Once you identify all the people you serve, selling becomes easier.
Exercise:
Apply this to your own business or career. List out as many different people or groups that you serve as possible.
If you truly show up in service, selling yourself is easy.
3 Things I’ve Loved This Week
Quote I’m Enjoying
“I’ve always imagined that paradise is a kind of library.” -Jorge Luis Borges
Book I’ve Loved
I just started reading Win Every Argument: The Art of Debating, Persuading, and Public Speaking by veteran debater Mehdi Hasan. It is a great primer about debate – both the tactics and strategy.
I started reading the physical book, but have also enjoyed the audiobook, which has recordings of many of the transcripts Hasan shares.
Website I’m Excited to Share
I’ve been writing on the Internet since 2008 – and most of it lives on my personal website. I've been meaning to update my personal website for years, but real business keeps getting in the way.
Well, I finally did get it updated, and am so pleased to have a hub for all of my work that I’m not embarrassed to share.
Check it out: www.robinpzander.com, kick the tires, and do let me know with errors!
Want more?
|
The Snafu Conference is an immersive 1-day experience about authentic selling in a chaotic world. The summit will take place on March 5, 2026 at the Oakland Museum of California. Ticket prices go up soon, so get yours now!
|
|
Responsive Conference is coming back in 2026! With AI and a changing economy, our jobs and careers are changing faster than most of us can adapt. Attend Responsive Conference and learn how to keep up with change. Ticket prices go up soon, so don't wait!
|
|
A few months ago, I began sorting Snafu articles into categories and realized how many were really How-Tos — fasting, buying a used car, raising a puppy, buying a house. This e-book collects those experiments and what I learned along the way. Download it free.
|
Until next week,
Robin
