Peter Attia: A big part of my problem was performance-based esteem. The drug that I needed, Bari, was performance. Not food, not alcohol, not sex, not gambling, but performance. My whole life was a journey to find things to do well in: in school, in surgery, in swimming, in boxing.

Bari Weiss: Most of us hear that and we think, “Just a Type A, high-performing person.”

PA: It depends on what the root of that is. There are some people who, I think, are Type A, and the root of that is love of the thing that they’re doing. And I’m not saying that I didn’t love the things I was doing. But the main impetus of those things was to get the esteem, was to be worthy.”

This resonated deeply with me. Until recently, my ability to run a successful business and make a positive ‘dent in the universe’ was my primary standard of self-worth. If I couldn’t do that, who was I?

Life has a funny way of making us confront the lessons we need to learn. I quit my job before the birth of my daughter in the fall of 2019. I was still at home when the COVID lockdowns hit six months later. Rather than return to work, I suddenly found myself at home with my infant and toddler (and my husband and my au pair), trying to create screen-free normalcy without the support of school, playdates, or library outings.

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On various forms, I confronted the field, “Occupation”. I didn’t really know what to say. “Former entrepreneur?” or “I swear I used to be productively employed?” For so long, in my childhood, my father had disparaged raising children as a worthwhile pursuit. My inner honesty required me to write, “Homemaker,” even as my thoughts ran in circles questioning what the heck that even was. I wasn’t producing anything of value that could be traded for money or quantified in any way, I told myself.

My children returned to school in the spring of 2021 and, relieved, I immediately began thinking about what I wanted the second half of my career to look like. The concept for Origin Stories began to emerge. I started interviewing people and I had an ambitious, large-scale vision of what I wanted to achieve.

Life sat back, grabbed a drink, and handed out the advanced assignment.

I got a major health diagnosis just weeks before launching Origin Stories, and realized it would require significant surgery and downtime. I let my interviewees know that my project was delayed and focused on the immediate future. Thankfully, I made a full recovery by the end of that year, but throughout 2022 I found myself mentally paralyzed. I wondered, “How can I commit to any meaningful endeavour, when I could be called away due to school closures or surprise health issues at any time?” and “Who am I, if I am not able to commit to a meaningful endeavour?”

One interesting data point came in March 2022, when I spent a month building a team and pulling together a website to help Ukrainian refugees find shelter, working 16 hours days. It reminded me that I still had my startup-CEO chops. It taught me how to ask my husband and au pair to step in and step up when I wanted to focus on work. It also helped me realize that I could make this lifestyle work, but that I didn’t want to anymore.

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I recognized that nurturing my children, spending time with my husband and having time for friends and family were important values to me. I was *choosing* to spend time on them, rather than on work. How to square this new idea with my performance-based self-esteem? I had no clue, but it was the right question to ask.

The next data point came in early 2023, as I was preparing to teach a personal leadership class at UMD. I was trying to come up with a prompt to help my students overcome the paralysis some face when considering what they see as impossible goals. I wrote: “The question isn’t, ‘Can I do it?’ but ‘How can I do it?’

This was transformational. It was clear that work, the way I used to do it, wasn’t compatible with the whole constellation of values I wanted in my life at this point. I had to think about work a different way: if I wasn’t going to work 16 hour days to build a world-changing company (and thus feed the performance-self-esteem monster), how was I going to work?

I decided I was going to do work that was meaningful to me, which increased my knowledge and skills around my chosen goals and gave me a sense of moving forward, even through the repetitive, circular aspects of raising a family. It didn’t matter if it changed the world or earned me accolades; it was enough if it had an impact in my sphere of influence and paid my bills.

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I noticed that was I hesitant to launch Origin Stories because I didn’t think I could do it at the massive scale I envisioned, given the time constraints I had voluntarily embraced in my life. When I took my own advice, and asked, “How can I do it, within the time I have?” things started shifting.

I know that massive social media growth requires daily posting and videos, and that my target Gen Z audience is on TikTok. What felt possible to me, however, was a bi-weekly Substack post. I added Instagram for my younger audience, and LinkedIn for parents and educators. I considered my time availability: I had some 12 weeks left of the academic year, before summer set in with its travel plans and patchwork childcare.

I made a deal with myself: I would publish twice-a-week for 12 weeks, then take a summer hiatus to meet my other commitments. I would return in the fall. This was so far from the perfect social media strategy I imagined, but it was what I could do. And I did it.

I have 20 published posts, some paying subscribers (including one I don’t know personally, THANK YOU) and 1,250 monthly views. I’ve recently attended the Eastern Association of Colleges and Employers (EACE) conference, and was able to point to Origin Stories as something that I am actually doing, not something I aspire to do. It feels good.

And now I am going to take that summer hiatus, teach my summer intensive class, learn from students (my audience) and enjoy time with my family. I won’t be perfect, it won’t feed the performance-monster, but I will love doing it and I will be happy.

I’m looking forward to re-connecting with you all in the fall, and sharing many more exciting Origin Stories.

Have a great summer!

*Peter Attia on Bari Weiss’ podcast “Honestly” June 1, 2023: YouTube, Apple. Relevant discussion occurs between the 59min and 1h08 marks.

Back then, there was a focus on footfall data. Knowing how many people walked into a certain restaurant, store, or point of interest could be predictive of its popularity. For instance, we could observe whether a negative news item impacted traffic to a retailer. Everyone valued this insight: the merchant, the distributors, the suppliers, and the industry analysts.

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I started out consulting, helping companies unlock the value of their data. That’s how I met the science team of Plurilock. They had a biometric behavioural data algorithm – a way of identifying a computer user by their typing style - and they were seeking applications. I looked at e-commerce fraud prevention and internal security and compliance. Ultimately, the most promising one was using the algorithm as a method of authentication.

We had to overcome a ton of hurdles in taking academic research and turning it into a product, which didn’t work the first time. No product survives first contact with the customer. We took those learnings, put them back into the product, and kept going.

As I kept pointing out what had to happen to grow the business, I was rewarded with more responsibility. I went from consultant to Director of Business Development to Chief Executive Officer. I wasn’t looking for the CEO gig. I just saw tremendous opportunity for the company, and I didn’t want to squander it, so I kept making suggestions.

The day Plurilock went public, nothing fundamentally changed. I woke up and still felt the same. I would roll into meetings in a hoodie. It drove the investment bankers crazy! That’s the difference between a tech startup and Bay Street*. But my identity isn’t wrapped up in it - I try not to let the change in role impact me personally.”

*Bay Street is Canada’s Wall Street

In the same way that he got his original role at Terapeak - by demonstrating what he could do - Ian got the CEO role at Plurilock by articulating a vision for where the company should go. He has grown it from startup to $65 million in revenue in 2022.

What do you think comes first - the title or the role? Do you need to get the title to do the work, or do you do the work to get the title?

I felt self-conscious about not having a degree, but I wasn’t sure how much value university provided beyond the credential. I compensated by working harder. At the time, I didn’t know how unusual my approach actually was.

My experience at Terapeak became an unofficial MBA for me. Having just raised a $4 million Series A to grow its e-commerce data analytics offering, the company was experiencing frenetic change. I saw several rounds of growth and layoffs as the company experimented with business models until the investors brought new management and a focus on the bottom line.

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I was hired to do Enterprise Sales and mentored by a rough-and-tumble Texan. He taught me to price for value-added to the customer rather than for cost-plus-profit. Also, instead of starting small and upselling over time, his view was, ‘Let’s charge as much as possible upfront and if they don’t sign, the deal’s off. What’s more, we’ll blacklist them.’ We closed a $3.1 million deal in 45 days, on the last day of the fiscal year, on a Sunday. There were huge celebrations. We went whitewater rafting and duck hunting in Houston. We drank moonshine out of mason jars. I almost shot my boss. It was tremendous.

It was also educational; I wasn’t familiar with that level of tenacity and conflict. In some cases, it showed what’s possible, but in others, it showed what not to do. It was akin to my health challenges in high school: they caused problems, but they also taught me to push through fatigue and get work done. I learned that experiences are not inherently good or bad, just valuable.

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Throughout this, Terapeak faced a risk: it was at the mercy of the parties providing it with e-commerce data. On my own time, I wondered whether I could mitigate that risk and gain unique insight by combining different types of data: not just e-commerce, but also location, weather, and more. That’s the premise on which I founded Exapik in 2015.”

*Terapeak was acquired by eBay in 2017

What matters more? Getting the credential, or showing you can do the work? Tell us in the comments.

Everyone aspired to ‘work on the barge’ during Vancouver’s annual fireworks competition. I worked alongside international teams to load the barge, dig mortars into the sand, and wire them up. After the show, we’d sort through what was left. First, we’d make sure it wasn’t fizzing. Then we’d disarm it, get it out, level the sand, and prepare for the next show.

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I loved new gear and capabilities. The people working behind the scenes were highly skilled both mechanically and digitally. There was a sense of pride and craftsmanship. And there was an adrenaline to live events that I didn’t get with film or TV. Things needed to happen at a certain time. I had to prepare ahead of the setup window because if I arrived on-site without the right stuff, I was hooped. I got good at dealing with adversity and bullshit gear. It was very satisfying.

When I was still figuring things out, this life was tremendous. Over time, I realized my progression only consisted of bigger shows and venues. There were guys twice my age doing the same things. It was lots of physical work, late hours, and little job security, so I wondered about my next step. When my girlfriend moved to Victoria in 2009, I found myself commuting back to Vancouver for work. I decided the Olympics would wrap my production career.

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I began looking for interesting companies rather than specific jobs. Startups combined my interest in entrepreneurship and technology. Big data is a specialized application of IT and, like with pyrotechnics, I was drawn to the idea of doing something highly skilled that few others could do. That’s what attracted me to Terapeak, a startup analyzing big sets of e-commerce data to generate insights for customers. So I set about getting a job with them, even though I didn’t have a college degree or formal experience in IT.”

Skilled work is often glossed over as a career path, but it can lead to growth in self-confidence, and a sense of pride and craftsmanship.

If you took college off your roadmap, what skilled trade would you pursue? What skilled work have your done? What did it teach you?

How did Ian go on to become CEO of a listed company? More in the next chapter.

My whole family were teachers: parents, aunts, and uncles. I grew up middle-class in a Vancouver suburb called Surrey. It once held the record for car break-ins, but I didn’t realize it was a bad part of town until late one night when I found a dead body at the end of the street.

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I was a ‘reluctant attender’ in high school. It didn’t help that I was exhausted in the morning and wide awake at night. Years later, I learned that certain food sensitivities make it hard for me to manage my energy. Some teachers noticed that I had potential but demonstrated it outside of the standard test environment. They gave me other ways to learn: with hands-on work or on my own time.

My school was connected with a community theatre, and I was drawn to the technology aspect of stagecraft. I negotiated with my theatre teacher to swap from a ninth-grade drama class to an eleventh-grade stagecraft class. The teacher agreed because I showed initiative: I volunteered on my own time and learned things independently.

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I started doing in-venue production. I was responsible for the light and sound as well as the health and safety of the venue. It was thrilling to be answerable for tens of thousands of dollars’ worth of gear and the enjoyment of a couple-hundred people. I also did computer work and managed another school district’s Linux servers. I don’t think anyone knew I was in ninth grade. No one asked, and I didn’t tell.

By the time I graduated, I was working a lot – not because I had to, but because it was fun. I toured with some rock’n roll bands. I was unsure about the future but not panicked. My time horizon wasn’t more than a year: enough to schedule a tour or plan a trip to Southeast Asia. I didn’t have a long-term strategy. There was no family pressure to attend college, no expectations. My future was my own to figure out.”

Ian struggled with the structure of high school but showed lots of initiative and deepened his skills in his areas of interest. What non-standard interests did you lean into in high school? Or what do you wish you had pursued?

How did Ian become CEO of a listed company? More in the next chapter.

The process of "becoming” is such a challenging one that it dominates our literature and culture. In Greek mythology, a recurrent theme is one where fathers are killed by their sons. Sons have to revolt against their fathers to claim the universe*, or suffer by subjugating themselves to the old way of doing things.

Growing up, the movie that captured this theme for me was “Dead Poet’s Society.” Set in a strict all-boys boarding school, it features the arrival of a new English teacher, Mr. Keating. He asks his class to tear out the introduction of their poetry books, which offers a mathematical formula for rating poetry, and encourages them to develop their own appreciation of the works and find their own voice. Neil, one of the students most drawn to Mr. Keating, discovers that his teacher is an alumnus of the school and was a member of its unsanctioned "Dead Poets Society”, which met in secret to read poetry. Neil revives the society and develops a passion for Shakespeare. Fearing disapproval from his father, who values discipline and athletics, Neil fakes a permission slip from him to perform in the school play. His father sees his beautiful performance, withdraws him from the school, and places him in a military academy. Seeing no way to live his values, Neil commits suicide.

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This struggle is beautifully captured by Cat Steven’s song, “Father and Son”, in which the father argues for a calm, stable progression through life: “Find a girl, settle down, if you want you can marry.” Meanwhile, his son poignantly reflects, “From the moment I could talk, I was ordered to listen” and, “If they were right, I’d agree, but it’s them they know, not me.”

When I chose to finish my book, “GenXpat”, instead of attending business school, I was not only deciding between taking a chance on my book vs. the predictability of getting an MBA, but also between incurring my parents’ worry and disapproval if I were to become a writer vs. calming their fears about my future if I were to get a well-known diploma. I remember vividly thinking at the time that I could not achieve my values without disappointing them and damaging our relationship - I had to give up my desire for their approval and support to go my own way. In effect, I had to choose between (metaphorically) killing them to claim the universe, or killing my spirit. Publishing the Polish version of my book, in their country of origin, felt like coming full circle.

Since then, I have wanted to figure out a better way for parents and children to communicate about their children’s futures. Pitting one side against the other, with one winning at the cost of the other, is tragic. I believe in a process for young people to speak with their parents, understand each other’s goals and concerns, and create a plan that respects everyone’s needs, as Guy and Halelly did.

Have you found an effective way to communicate about different values across generations (young adult to parent, or parent to young adult)? Share in comments!

As a working mother, I had concerns: what quality of education will he get if he homeschools? Will I need to manage his self-study program? I’m not an educator and I didn’t feel prepared to teach him. I also have my own leadership development and training business to run.

Yet Guy was hating school and in constant conflict with his teachers. He wasn’t benefitting from the school’s quality. I asked him to research options. He found a program that assigned weekly work packets, with regular in-person meetings. He would have to maintain a certain average. The process was between him and the school. It didn’t require any teaching from me as a parent.

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For months, Guy had insisted, ‘I want to skateboard as my career and use daylight hours to practice and film. If I’m not successful, it will be your fault that I couldn’t put in the time.’ We took this to heart. We realized that there is no guarantee that he’ll succeed if he focuses on skating, but he certainly won’t succeed if he doesn’t skate. We also looked at the alternatives. If independent study didn’t work out, he could return to school and graduate a year later, but setting him up to live with regret would be irreversible.

We have friends who were more forceful in pushing a traditional path, but we’re not like that. We believe in individuals pursuing their values and we weren’t worried about how people might view our decision. We also knew that Guy has persistence out the wazoo. He wouldn’t miss his opportunity.

So we agreed to his plan. He had to take ownership of his education. One miss and it was back to regular school. His motivation to do his work increased and it was a relief to see his grades improve. More so, it was a relief to no longer see him suffering. It removed a huge stressor in our family and our relationship got better. Guy graduated in June 2019, and he skates full-time now. We’re proud of the progress he’s making towards his chosen goals.”

I’m really interested in the process by which young people and their parents navigate decisions around education and career. If you have faced a struggle in this space, I’d love to hear your story! Comment or message me.

Skating is incredibly freeing because I get to do what I want. It’s not a team sport. It’s not even a sport; it’s a way of life. I can get so creative with my board. Like dancing, there are many styles. Vert skating is ramps and skate parks. Street skating is all about stair sets and rails.

My challenge in skating is to get more confident on my board. Some people grind down rails like it’s nothing. I can’t get myself to go up on a rail; I’ll roll up and turn away 100 times. When I finally do it, I stop, but that’s probably when I should keep going. I’ve gotten over blocks like skating down gaps and stairs. Going fast. I have to keep doing it until my brain realizes I can do it.

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Sure, there’s a fear of getting hurt, but confident skaters see ways in which they can get out of a bad situation. I think of the worst outcome possible. Yet hesitation is how I get hurt in skating. I have to trust myself.

Skating is 80% mental, 20% physical. I must learn a trick in my head before I can do it in real life. I can spend a whole day visualizing how I will do it. It’s also physical. To pop my board a certain way, I need to learn where to place my feet and develop muscle memory.

A few years ago, I met a kid at Woodward whose dad owns Stereo Skateboards. When I sent him a part in fall 2019, he liked what I was doing. They sponsored me and posted pics on their Insta. I also got shoes from New Balance and trucks from Ace as a result of my outreach.

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Then a friend came from Atlanta to meet with the WKND team. He invited me to their Warehouse Day, and I skated with them for a week. Then I filmed with them. I’m in the ‘Van Down’ video that has over 197,000 views. That’s when I felt like, ‘I can do this.’

I am hopeful about my future. I’m either getting paid or close to it. My challenge, career-wise, is to put something out there for people to see. I don’t have a solo video yet, so that’s what I’m working on. I want to get my name out there.”

June 2023 Update: Guy is featured in WKND’s ‘Junior’s In Training’ film, released two weeks ago. It has already amassed over 109,000 views.

Stay tuned for the last - unique - instalment in Guy’s story: his Mom’s perspective on his career choices.

Guy is constantly working on improving his craft - both his mindset, and his physical skills. How do you improve your craft? Tell us in the comments.

I kept asking my parents, ‘How can I get really good at skating if I have to focus on things I don’t care about?’ and, ‘Didn’t you ever have a dream?’ I wanted to do this more than anything else. I felt I had potential. They saw it too.

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Finally, they agreed. It helped that I had found options that didn’t require effort on their part. I started independent study at Oak Park. Every week, I got a package of material to work on. If I wanted to keep skating, I had to keep up with my schoolwork. I grew to enjoy school more, due to electives like art history, cooking, and music. My grades went up.

My skating improved a lot, all due to practice. I’d go downtown and skate at the parks where the Pros were. The way to progress in this world is to film street spots called parts. You send them to companies via Instagram or email. At first, you’re Flow: you get free stuff, like boards, clothes, or shoes. It’s publicity for them. Then you’re Amateur, which means you join their skate team, get some coverage, and maybe get paid for photos that are published. Then there’s Pro. Your name goes on a board, you have your own shoe model, you get royalties. But to go Pro, you need a big following.

I graduated in 2019. I was skating a lot, but I wasn’t even Flow yet. At times I’d get down on myself that it wasn’t happening fast enough. I debated how I would know if I wasn’t succeeding: I think it would be if I were doing the same thing all the time. I’d never call it quits though. I’d keep trying to find ways to make a living in the industry: photography, video editing, warehouse work, gear sales, or team management.

But I haven’t had to look at those options yet. That summer, I filmed some parts and sent them to the industry. And I started getting interest.”

How do you know if you are succeeding? Share in comments!

Stay tuned for part 2 later this week.

In between Origin Stories, I will be sharing insights related to purpose & career, and answering reader questions.

One of my favourite parts of Mimi’s story is when she reflects on her motivation, “My hope is to set an example.” Through her work, she hopes to show what’s possible for a young, Black, Asian woman in Charleston, SC and offer inspiration to others.

The topic of motivation came up again yesterday when I watched the penultimate episode of the wonderful Ted Lasso series. In it, Jamie Tartt, AFC Richmond’s star player, reflects on his motivation to play soccer/football.

For many years, he was driven by a desire to show up his abusive, alcoholic father, “I always did what I did because … f*ck him.” Things come to a head after a match, when Jamie’s dad hurls insults at him for losing while asking for a tour of the football pitch. Jamie finally stands up for himself and says, “I’d rather not.”

A year later, Jamie confesses to his mom, “I thought I was finally rid of him… but now that I don’t give a sh*t about him, it’s like … I’m impotent… in my soul.” Jamie is no longer playing to spite his father. He feels lost and his game suffers. He doesn’t know what he is playing *for*.

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This resonated deeply with me. When I left my corporate job and decided to write GenXpat, as a first attempt to explore my interests, skills and experiences, I didn’t have a strong sense of certainty in my mission. The writing felt good and I felt confident, but those pesky voices at the back of my head kept saying, “What if it doesn’t get published? How will I make a living?” As a backup option (and to appease my doubters), I studied for my GMAT and applied to business school.

I got in.

In December 2003, I found myself with my first draft of “GenXpat” three-quarters finished, a substantial tuition deposit paid and a one-way ticket to Europe to start my MBA in January. I was anguished: I had to choose between my book - the first thing I had done for myself, almost complete, but with no guarantee of success - versus admission to my dream business school and an on-ramp to a high-potential career. How could I choose? What choice should I make?

I wish I had then had the benefit of Ruth Chang’s TED talk on the topic of hard choices. She begins by explaining why some choices are hard: they require you to choose between things that are mutually exclusive, but not directly comparable. Choosing between two MBA schools that are similar, but one offers you a $50,000 scholarship, is easy. The are comparable, and one is clearly better than the other. But choosing between an MBA and an unfinished book is difficult because each option is different in kind - it represents different values and a different end-game.

Her crucial insight is that these kinds of choices represent a unique opportunity. Rather than agonize over which choice is better, she makes the case that we should consider which choice better represents who we are, and whom we want to become. In fact, Dr. Chang says, “When we create reasons for ourselves to become this kind of person rather than that, we wholeheartedly become the people that we are. You might say that we become the authors of our own lives.”

After weeks of agonizing about my choice and my future, I decided that that I wanted to be the kind of person who finished my book and submitted it to publishers, who was willing to take a chance on myself, regardless of the future. So I called the school and requested to defer my admission. I was told that I could do so, but that I would have to reapply and might not get admitted if I was not competitive in the new pool of candidates, losing my deposit. I took that chance because of whom I wanted to be.

Mimi’s values both shape and shine through her business driving it’s success. Jamie finds his mojo when he allows positive values - his love of the game, and of his team - to inspire his play. As Dr. Chang shows, every time you face a choice, you have the unique opportunity to express your values and become wholeheartedly who you are.

So, next time you face a decision, ask yourself: who are you now? And whom do you want to become?

My former 50/50 business partner was white and ten years older than me. People entered our store and assumed that I was a student working there. I used to put myself in a bubble and think, ‘This is not affecting me.’ But it was. Now I seize the opportunity to show, ‘Yes, it is possible for a young woman of colour to own a successful business here.’

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There is a microscope on my business because I am young, Black and in Charleston. With everything I do, I’m calculating, ‘Is this the right thing to say? Will this make clear where I stand on race and gender equality?’ I want my store – our team, our products and our brand – to fully represent my values. At the same time, I want people to support us not just because we are Black-owned, but because they love our products and appreciate our brand.

I’m blessed right now. Unless there is another pandemic, we’re in good shape. My biggest obstacle is not playing it too safe. Last holiday season, when we sold out of a certain product, I asked myself, ‘Will we really sell another 50?’ I’d order less and we’d sell out again in a day or two. I’m learning to think strategically and invest in the business.

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Many of my goals have been achieved sooner than expected. Now I am catching up and considering the future. I would love for my store to be a staple in the neighbourhood, one that brings customers back, again and again. While I’m not aiming to expand or earn millions, I am learning how healthy financials can serve as a foundation to allow me to focus on impact.

My hope is to set an example. I want to show that you can be young, Black, Asian, with big curly hair (or whatever), and own a business and live a full life with peace in the space that you’re in. One day, if a kid enters my store, gets inspired, and says, ‘Mommy, I want to have a store like this,’ that’s what it’s all about for me.”

What are your values? What is it all about for you?

It had been a long road to reach this point. When I began selling tassel earrings on Etsy, I would do anything to please a customer. Some wanted a boho tassel, others a nautical look. As custom supplies piled up, I realized I was doing twice the work for folks who were not my core customers and unlikely to order again. I learned to refer them away.

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Two years later I opened my first shop with another Charleston maker. We featured local makers and artists, as well as our own work, and I kept growing The Tiny Tassel online. Equal partnerships aren’t easy. By mid-2020, we parted ways and I was thinking ahead.

Did I want to continue as a solopreneur, making and managing everything myself, or did I want to grow as a business and start hiring people? The times were confusing: COVID was slowing things down in-store, yet the push to support local businesses was driving online sales. Then the dark events that led to the up-swelling of the Black Lives Matter movement brought attention to Black-owned businesses like mine.

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In June, The Tiny Tassel was mentioned on the ‘Gal Meets Glam’ blog. We sold $20,000 overnight. I thought it was a website glitch at first. Then we did the Today Show and grew from 100 to 4000 orders per month. People thought we were a major business, but it was just me, my mom, and my friends filling orders in my apartment. It was nuts.

Though it was hard to build a team in COVID, today there are seven of us. My Mom makes our clothing and we have a jewelry-maker, an online-order fulfiller, a retail director, and two marketing specialists. My sister is our unofficial CFO.

With social distancing in force, I didn’t expect to open another store immediately. Yet a corner space freed up in a neighbourhood I love. Since these go fast in Charleston, I told myself, ‘I’ll call the number and if it’s still available, it’s meant to be.’ And here we are, open for business.”

Stay tuned for part 3, coming Tuesday!

When have you taken a big risk in adverse circumstances? How did it play out?

I grew up in Spartanburg, SC. My parents were entrepreneurs – a bail bondsman and a seamstress – and I worked for them as a kid. I learned to speak professionally when I answered the phone and asked my Dad’s customers for payment. I collected pins and cleared thread from sewing machines for my Mom. We spent a week in Charleston each summer and it became a second home for me. I wanted to attend college there even though the school didn’t have a fashion program. Instead I chose Communication, a major that would allow me to ‘do anything’.

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Although I’ve worked in clothing retail since high school, it took time to find the right fit. Larger chain stores felt impersonal and excessively sales-focused. I felt I had more impact as the manager of a family-owned menswear store. I advised customers, learned product placement and stock management, and helped grow the business to record sales, but I was still living pay check-to-pay check.

That year, my sister gave me hot pink tassel earrings for my birthday. She said, ‘You know you can make these, right?’ So I looked at Pinterest for DIY tutorials. I created a storefront on Etsy and The Tiny Tassel was born. The first order from someone who wasn’t family or a friend-of-a-friend was a major moment for me.

For over a year, I sold menswear by day and crafted earrings, bracelets, necklaces, and keychains at night. One day, I realized that my job was causing me to miss out on growth for The Tiny Tassel, and the stress of two jobs was taking its toll. At work, many of my customers were conservative and showed prejudice, while at The Tiny Tassel my customers were excited, encouraging and kind. I knew I had to make a change.

My sister, an accountant, helped me calculate how I could do The Tiny Tassel full-time. I set a savings goal and gave six months’ notice. I did as many weekend markets and pop-up shops as I could, and began wholesaling my products. My last day as an employee was Christmas Eve. I became wholly my own boss on January 1, 2017.”

Stay tuned for part 2, coming Thursday!

Have you ever built a side-hustle into your main gig? Share in the comments.

One of my favourite parts of Vivian’s story is where she ponders the meaning of work, asking, ‘What is good work? What is success?’

My first job after graduation was a marketing role with Procter & Gamble. When I accepted the position, I had no idea what marketing was. But it was well paid, with a good firm, a great boss, and in an exciting location. It was the best answer I could find to the question, ‘What can I do?’

For lack of any other model, I approached my work like a school project or an academic assignment. I saw it as an intellectual puzzle culminating in a report and a recommendation, rather than a process of bringing people together to meaningfully improve the lives of our customers.

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Without that connection to reality, I was wrapped up in all sorts of extrinsic metrics: Did my boss think well of my presentation? Was I doing as well as or better than my colleagues? Would I get a promotion sooner? And I felt a gnawing sense of uncertainty about my self-worth. I worked insane hours to compensate. I burned out.

I considered switching jobs to consulting, but a quiet voice in the back of my mind told me that it would be more of the same. I wouldn’t have addressed the underlying cause of my burnout. Instead, I sought career coaching at The Right Mountain with Jim Hayhurst and Michael Reddy.

Michael asked me: ‘What do you like to do? What do you do because you feel you ought to?’

I was floored. In my whole life, I had never considered what I liked to do. I had so consistently overridden my interests and preferences, in favour of what was most marketable, that I couldn’t easily identify them. This began a long process of self-discovery.

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In the short term, I identified a few things: that I love to write, that I love learning about people, cultures and behaviours, and that I had extensive experience living, studying and working abroad.

One day, in the shower, these things came together: I determined to write a book about the new wave of young professionals living and working abroad. And I had experienced this first hand when P&G relocated its European headquarters, moving 2000 or so people from England, Germany and Belgium to Switzerland.

While I was proud of the publication of “GenXpat”, I was ultimately more proud of something else. This was the first thing I had done for myself – based on my own interests, on my own initiative, and certainly not for pay or glory. I had quickly learned that, ‘I used to work at P&G’ drew interest and a certain hope for my future, while ‘I’m writing a book’ caused polite coughs and changes of topic. Despite this, I felt more confident in myself than ever before. I was beginning to answer the question, ‘What do I want to do?’

Reflecting on this time, I can see that my ideas of good work and success had changed. Instead of worrying about creating a perfect presentation to impress my boss, I was thinking about content that was meaningful to my readers. Instead of clocking 8 hours and working overtime, I worked 5-6 hours a day on the things that mattered most. Instead of drawing confidence from my title and pay check, I drew it from enjoying my work, developing new physical skills, and connecting with people.

So what do you want to do? What does success mean to you?

Anna approached me and Oana about Flax Sleep in fall 2017. She couldn’t find reasonably priced linen bedding and saw a gap in the market. Thanks to a background in hospitality, she knew the product and customer experience she wanted. Together, we envisioned European-sourced linen made affordable by being sold direct-to-consumer.

In March 2020 our future was unclear, ‘Would a slowing economy under COVID stop us in our tracks?’ No, and instead e-commerce boomed as people stayed home and shopped online. Now our challenge was to secure supply through the end of the year and the peak holiday season.

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Pursuing growth isn’t something I do very well. I came to business thinking, ‘Let’s do this to stay alive,’ but that wasn’t good enough for 2020. We got business coaching both as a group and individually, and it was transformational. It helped us shift from a fixed to a growth mindset.

I had already gotten past the idea of getting a job, keeping it, then retiring. But my conservative mindset had deep roots. As a lawyer, I identified risks and suggested a prudent path. As a business owner, I can’t avoid risk. I can only choose worthwhile risk. It’s constant work for me to face fear and uncertainty.

‘What is good work? What is success?’ I used to value checking visible work off my list. Now I focus on what I can do to move the business forward, and that can be simply listening deeply to my team. I used to seek extrinsic markers of success, such as revenue growth or the sale of our business. I now notice intrinsic rewards: building something with my friends, working from home and seeing my family, and coaching women entrepreneurs in my community.

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Our coach helped us jump-start on big questions in the post-holiday lull. Should we launch in the US? What next-level IT solutions do we need now that e-commerce has shot ahead? Instead of stalling, I’m finally pro-actively thinking about how I can continue to grow.”

How do you keep going after the honeymoon phase of a new idea wears off? How do you deal with fear and risk? Tell us in the comments.

As a lawyer you only see the last 10% of the deal. After five years on the job, I wanted to see the decision-making that leads up to it. I was curious about how businesses operate on the inside. I was also considering how to balance my career with finding a partner and raising a family. I sought more predictability in my schedule.

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So I started talking to lawyers who worked for businesses rather than law firms. This is a strategy I use whenever I’m unsure – I reach out to people and ask questions. In the end, I became in-house counsel for the Business Development Bank of Canada. Its mission is to support entrepreneurs. I helped craft policies that fulfill its mandate while also protecting the bank. The hours were more regular, allowing time for my interests and personal goals.

‘What comes after security?’ asked a voice inside my head. I had worked hard to check the boxes, and I had a nice life. Still, the law can feel limiting at times, so I wondered: ‘What else I can I do with the next 30 years of my life?’ In the end, I did what I always do – I talked to a lot of people. Entrepreneurship was having its heyday then, with many podcasts on the topic, and I looked for ways to get involved.

I hung up my shingle as an advisor to entrepreneurs, which was a big transition for me. I had no schooling to prepare me for this and no certificate to give me legitimacy. My parents didn’t get why I would abandon a secure legal career for this. Yet I got clients by word of mouth and loved helping entrepreneurs bring their ideas to life. I especially enjoyed thinking through financing options.

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What I didn’t expect was that 6 months later, my friend Anna would approach me about starting a linen home goods company. Or that I would join her in this new adventure, severing ties with my educational background and professional experience, and the security they represented.”

Have you ever wondered what lies beyond the ‘safe’ path? If a secure income were guaranteed, what would you take a chance on? Tell us in the comments.

What do you love failing at?

“In failing for two weeks at journalism, I knew I loved it.”

Bob Woodward started working at the Washington Post for free. None of the 17 stories he wrote during this time was published:

I love failing at speaking foreign languages. I enjoy puzzling out what words I already know that might get my message across (as I had to when I was trying to buy barbecue lighter fluid - liquido para encender el carbon - in rural Mexico. Several store clerks looked at me with incomprehension, until one finally said ‘gasolina’. So that’s how they roll.)

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I love failing at starting new ventures and mastering new skills. My first attempt at making an Instagram reel yesterday gave me joy far out of proportion to the quality of the outcome.

I love failing at kiteboarding. It was a long learning curve in the freezing waters of Squamish, BC, and yet I knew without a doubt that hours of getting dragged and slammed face first would be worth it. Even though I can now get up and ride, there is always a new skill to learn.

So what do YOU love failing at? Share in the comments…

I had started The Roots of Progress in 2017. At first it was just some notes from my readings about the dawn of the Industrial Revolution. I was interested in what drives human progress: how did mankind emerge from the caves and build the modern world? Why did it take so long for progress to take off?

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Some two years later I posted, ‘Why did we wait so long for the bicycle?’ It went viral. Around then, Tyler Cowen and Patrick Collison wrote ‘We Need a New Science of Progress’ in The Atlantic. Suddenly, there was a name for what I was doing and a community of people who were interested in it.

I was interviewing with exciting tech startups at the time. It would have been easy to accept one of their offers. Yet I knew that despite this, I wouldn’t stop working on The Roots of Progress. On the other hand, if I pursued The Roots of Progress full-time, I felt no call to do engineering on the side. In that way, my choice was easy: The Roots of Progress was the only thing I couldn’t imagine not doing.

In another way, my choice was hard. For 25 years, my purpose has been to found a startup and have a huge impact on the world. The Roots of Progress is a new venture, but not a startup. It won’t scale to unicorn revenue and earn that kind of credibility. I’ve since come to see that a great intellectual product is another way to have a significant impact. Financially, a grant from Cowen’s Emergent Ventures has helped me to take the leap.

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In the past 18 months, I’ve been hired to develop a course on Progress, spoken about it, grown my audience, and begun working on a book. Beyond that, I can’t see very far into the future, but there is so much momentum and there are so many interesting opportunities that I haven’t looked back.”

Have you ever taken a great leap into the unknown? Tell us in the comments!

As CEO, no one but me was responsible for setting the direction or carving up the work. There were no constraints, guidance, or structure. At any moment I could be doing anything: strategy, marketing, hiring, or writing code. The weight of goal-setting fell on my shoulders.

Despite these challenges, I felt compelled to persist down an entrepreneurial path with the potential for huge scale and impact. I am very aware that my ability to live a comfortable life is due to those who came before me and struggled to bring breakthroughs to the world. While I can’t pay it back to them, if I have the ability to contribute at that level, then I feel an obligation to pay it forward.

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Yet my startup was lacking momentum. My goal at Fieldbook had been to create a relational database that was simple and intuitive enough to serve small business users. The product wasn’t quite right, but it wasn’t obvious how to fix it: simplify it to lower the cost of customer acquisition? Charge a premium to onboard upmarket customers? Could I turn things around by investing more effort? How would I know when to quit?

None of these questions had easy answers. Even Mark Andreesen says there is no formula, which is one of the reasons that being a founder is so hard. In a gut-wrenching moment, I shut down Fieldbook and accepted a talent acquisition deal. I realized that as CEO, I could hit every one of my goals but the company could still fail if I had set the wrong goals. Emotionally, it was hard not to have my self-esteem bound up in the dissolution of my company.

When I clocked in as Senior Engineering Manager at the acquiring company, I expected to eventually return to the startup world. I had no idea that my side project, a blog on the drivers of human progress, would suddenly gain traction and have me considering a mid-life career pivot.”

Stay tuned for Part 2, coming next week!

Have you ever struggled with the question of when to continue, and when to quit? Share your story in the comments.

I was totally naïve about it, not thinking in terms of risks or rewards at the time. I just wanted to learn more, faster, and enjoy the process. I had an idea that college would be a good place to learn Computer Science, but I never considered how dropping out of high school might appear on my application. My Mom had the great idea of calling it ‘homeschooling’ rather than ‘dropping out’ so we went with that.

She asked me to put together a curriculum for myself. That mostly worked well, but I got some things wrong. For example, initially I planned to use Isaac Asimov’s ‘Understanding Physics’ as a textbook, but I later realized that there were no exercises integrated with it. So I signed up at the University of Maryland, as a non-degree student, to take the relevant course. My plan for History was to read ‘The Story of Civilization’ by Will and Ariel Durant. Midway through book 1 of 11, it became obvious that I needed a new plan. Luckily, I knew someone with a PhD in History who suggested some readings and some written assignments, and provided feedback on my essays. For extracurriculars, I interned at NASA Goddard Space Flight Center and played saxophone with the UMD band.

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During my senior year, I attended a few college info sessions. Universities had no problem with homeschooling as long as I documented my work. In the end, my applications included good grades from my first two years of high school, strong SAT and AP computer science test scores, my essays, and reference letters from my mentors at NASA. I applied to Caltech and Carnegie Mellon and was accepted at both.

In high school, my future goal was to do a startup because I didn’t think I wanted to work for anyone else. By the end of college, I found that there were people I wanted to work for and I needed the experience. Still, within 10 years I had moved to Silicon Valley and was gearing up to face the ultimate challenge: building my own startup.”

Stay tuned for Part 2, coming Friday!