The Psychology Of Being Your Own Boss

An HBR article version of Gianpiero’s piece came out that is v easy to read. —JM

Our conclusion is that people in the gig economy must pursue a different kind of success—one that comes from finding a balance between predictability and possibility, between viability (the promise of continued work) and vitality (feeling present, authentic, and alive in one’s work). Those we interviewed do so by building holding environments around place, routines, purpose, and people, which help them sustain productivity, endure their anxieties, and even turn those feelings into sources of creativity and growth. “There’s a sense of confidence that comes from a career as a self-employed person,” one consultant told us. “You can feel that no matter how bad it gets, I can overcome this. I can change it. I can operate more from a place of choice as opposed to a place of need.”

The Psychology of Work Independence

This new study by Insead’s Gianpiero Petriglieri, et al is super useful not only to understand the psychology of the “gig economy” participants, but to understand the psychology of small business owners and entrepreneurs in general.

By clarifying the process through which people manage emotions associated with precarious and personalized work identities, and thereby render their work identities viable and their selves vital, this paper advances theorizing on the emotional underpinnings of identity work and the systems psychodynamics of independent work.

If I may translate that, it’s all about finding one’s identity in the work that they do — which when a large corporation succeeds, then the employee gets a win-win world. For a business of one, it’s the fruit of one’s success; for a tech startup, it’s also the fruit of success that generally gets lost when the company starts to scale. For a non-tech startup, or a small business in general that chooses not to grow, it’s the commonsense outcome of achieving financial freedom on one’s own terms. In their diagram, this part is the important part:

Their study is available until February 2018, and I have a local cache here.

Doughnut Shop Business Wisdom

In the December 2017 issue of American Way, a few mom-and-pop doughnut shops in Los Angeles were featured by Andy Wang. A few key takeaway quotes for me are:

“Our customers are like our family. We’re not going anywhere.” —Teresa Ngo of

“It’s been a great joy to say that it’s all because of Primos Donuts and because he and I devoted our life to doing what the customer wants.” —Celia Primo of on her husband and partner Ralph

“She made sure the customers are taking care of. When she saw a car, she knew who it was. She had their coffee and donuts ready. She would talk to the customers and build great relationships.” —Jim Nakano of on his wife and partner Miyoko

“People would rather have a hard-working immigrant family’s hand-cut donut that’s freshly made several times a day than something that’s just shipped frozen or made once a day.” —Mayly Tao of

“You don’t need to have 2 million dollars to go into business. You just have to have an idea and persistence.” —Stan Berman of

I especially love:

“… because he and I devoted our life to doing what the customer wants.”

This is definitely how this felt like for me growing up in a small business. —JM

No Plan B

Sitting with Hajj Flemings at WordCamp US, I heard a phrase from Hajj that stuck with me. He was describing the entrepreneurs he’s working with as folks who weren’t born with a silver spoon in their mouth. So they had no backup plan. No plan B.

They HAD to succeed. Failure wasn’t an option because they were out of other options.

Hajj then shared some wisdom from Mike Tyson,

“Everyone has a plan until you get punched in the mouth.”

It was a way to describe how someone who has already lost all their chances for success simply needs to get … back … up …. And doesn’t have the luxury to “design thinking” themselves with a slick 7-page PPT slide deck back to victory.

I’ve heard this moment described as the “oops moment” by a small business expert in Philadelphia. It is the moment that a miscalculation has been made — like having too much inventory on hand that isn’t selling, or trusting the wrong vendor to deliver on time — and the business goes bankrupt, immediately.

Because there is no Plan B available to these small business owners the way you can more often see in tech circles where some of the entrepreneurs are lucky to come from wealth circles where there is always access to more cash for them. They get to have the luxury of a good Plan B, Plan C, etc. Mind you, this isn’t all tech entrepreneurs of course.

The “no Plan B” mindset is also evident in the JUGAAD mentality in India — because extreme conditions can lead to unexpected innovations. So abundance of cash may not be the only way to see innovation occur — and for that reason you see a lot of innovation in the small businesses out there because they have no other recourse but to outrun their competition with everything they’ve got, and having nothing in reserve to draw upon if they fail.

Small businesses owners give me similar inspiration to what I took in from Silicon Valley startups while at Kleiner Perkins — I am so excited to get to learn from these “No Plan B” entrepreneurs. —JM

A Small Business Is Big Work

I had both the fortune and misfortune of growing up in a family-run small business. I say “fortune” because it shaped my later years of life in positive ways as it gave me a work ethic that has served me to this day; and I say “misfortune” because it meant that I was always working for my family after school as a child and all throughout my middle and high school years. But I wouldn’t re-live my life any other way.

It was a little shop in the International District of Seattle — a true “hole in the wall.” My parents woke up super early in the morning (between 1am and 3am) and worked into the late afternoon (5pm to 6pm) for six days a week. Often they’d work seven days a week. And myself and my siblings would be along for “the ride.”

This experience has helped me understand the small business owners that I have the privilege to get to meet these days by working at Automattic. I thought I’d share some of what I learn on this site to paint a picture of what “being your own boss” really means — which is hard, hard work. This is my first post! —JM