It’s taken me waaaay too long to finally put this information together, but since a lot of people have asked, here’s what one year of “underemployment” looks like since I quit my corporate job, the good, bad, and ugly, followed by what’s happened since.
For those of you who don’t want the details, there’s a section at the end called “Ten Important Lessons” for you.
August 29, 2014-August 29, 2015, roughly in chronological order
- had an existential crisis
- felt guilty
- realized that I’d worked 10 jobs since my teens with very few work days under 10 hours in the past several years (the worst was probably working multiple jobs both day and night shifts), that I’d been a diligent saver despite major, unexpected setbacks early on, and that I needed to be less of an asshole to myself
- also realized that I wrote a 65-page succession plan complete with visuals and hyperlinks to supporting documentation to my projects, as well as a tiered training curriculum that could easily be used to eliminate my job by teaching everyone else what I know about Lean methods and setting them up for better career advancement. Seriously. Who does that? I know how to quit in style.
- took two months off
- went to Iceland, went inside a volcano, hiked on glaciers and volcanic ground, picnicked on a fjord, saw the northern lights, nearly got lost in the mountains, skinny dipped in geothermal pools, began to restore as a human being
- took a road trip to Cincinnati to see old college roommates and a new baby in the group, visited my Milwaukee peeps a lot, and reflected on family and community vs my own life choices
- enjoyed fall to the fullest, corn mazes, pumpkin carving, pie baking, and fall hikes galore
- participated in Maker Faire, got slaughtered on day 1 by way too many children who wanted to learn to print; charged on day 2, dealt with fewer and better children, and made $150
- rebuilt my website
- started making art again :)
- after two months off, consulted in manufacturing and helped a $20 million printing company reduce paper waste alone by $50,000 in the first few weeks and devised a plan with their Senior Process Manager to cut down on $350,000 waste in the upcoming three months; tried all the things I couldn’t with a boss or larger team, including creating my own educational workshops to help people fight their own battles in the workplace; realized I’d make a killer consultant
- finally told my mom I quit my job and was relieved she wasn’t angry; began investing in and improving our relationship
- ran a 10k with my former coworkers and boss, because that’s the kind of ex-employee I am; tried to beat my old boss, lost by a minute
- practiced what I preached; reduced my cost of living, such as switching to a $10/month phone plan, getting rid of my gym membership, and renting my extra space on Airbnb
- started this blog
- “started” learning Spanish
- flew to Buenos Aires and landed on my birthday; experienced having a summer birthday for the first time
- lived in Buenos Aires for four weeks, largely as a listener and a mute (would you believe it?)
- actually started learning Spanish
- absolutely fell in love with Buenos Aires (did you know it’s the world capital of books?), ate a lot of gelato, dulce de leche, and medialunas and started my Spanish book collection
- spent three of those weeks in Buenos Aires doing my art residency at Proyecto’Ace; was seriously in the zone; conceptualized, storyboarded, carved, and printed an edition of 18 books, all in woodcut, which you can read about here
- serendipitously reunited with a friend from Milwaukee in Buenos Aires
- bought a plane ticket and flew to Ushuaia, Argentina, the southernmost city in the world and the beginning of my Patagonia journey
- airport lost my baggage; had first encounter trying to explain my problem in Spanish; luckily, most things work out
- did my annual polar plunge in Ushuaia immediately after a 36km hike since I missed it in Wisconsin, which drew more attention than I was expecting; got hollered at by various Argentines and tourists
- realized I didn’t miss the U.S. and debated never coming home
- learned how to ride a motorcycle on a windy day, on a gravel road, on a hill; got really good at picking the motorcycle up
- hiked through Patagonia for three weeks, met some of the most amazing people (two of whom I’ve since gotten to see again in Madison!)
- seriously, though, check out The Pack Track’s Facebook page: they are the best Aussie motorcyclists travelling with dogs that I’ve met, possibly the only Aussie motorcyclists travelling with dogs that I’ve met. I got to see them again in Madison and they’ll be touring the US through Christmas.
- committed to thinking, reading, and speaking almost entirely in Spanish; came out the other side of Patagonia conversational and with a distinct Argentinian flair to my accent, and slightly worse at English
- really missed fresh vegetables
- almost got stranded in the mountains again
- hiked up to see a receding glacier with a group of Argentinian men who didn’t speak English, found a baby bird who died shortly after; wrestled with my exhausted, English deprived brain; thought about my parents, the mountain I was on, life, and death
- arrived in Bariloche, Argentina, and knew immediately that I would love living there; mountains, lakes, chocolate, beer; $10 a night at a hostel with a lake view; done
- went hiking with an Israeli woman who had just finished medical school; she asked to see the book I made in Buenos Aires, so I brought the draft copy I had been carrying to dinner at the hostel that night. As soon as I started telling the story, I realized that half the people listening only spoke Spanish, so I had to tell the story in two languages, back and forth, page by page. I nearly gave myself a migraine, but it was a moment that taught me the power of language both to include and exclude, and I must not have done too poorly translating because one of the Argentines in the group later messaged me saying that story was one of the most profound moments of his trip. Anyway, it was at that table of travelers, surrounded by warmth, good people, and good food, that I knew I needed to go home and not cancel or delay my return flight.
- arrived in Chile, lost all confidence in my Spanish skills
- took the ferry to the island of Chiloé, started my second art residency at Museo de Arte Moderno
- found the best produce ever on that island
- learned pretty quickly that I don’t like living in isolation on a hill
- tried to make sense of it all, ended up just writing a lot and producing a bunch of shitty to semi-decent drawings
- loved my host couple, who took me bird watching; thought about all the strange recurring bird themes on my trip and worried about reading too much into things
- thought about gentrification and tourism over a cup of Yogi tea
- thought about money and value
- left Chiloé by yet another 20 hour bus ride
- arrived in Santiago, hated it immediately; felt super glad I didn’t move there three years beforehand to follow love; took the next bus to Valparaíso
- loved Valparaíso for its poetic beauty, hated the pollution and consumerist development; agreed to let a local man take me sightseeing on the basis of his Spanish being clearer than any other Chilean I had met (sorry, Chile). He was super sweet and we had a good day, so I only felt slightly bad.
- thought about how people use people
- returned to Buenos Aires, totally missed my flight
- learned how hard it is to argue/reason in a foreign language with airline employees to help you catch a flight before last departure for the night, especially when they don’t give a shit
- stayed awake for over 36 hours thinking mean things about American Airlines while waiting for the next afternoon flights
- debated once again about not going back to the U.S.
- returned to the U.S. and tasted good cheese again
- drew a lot
- finished, finessed, and framed all my new work for a solo show
- exhibited and sold work
- started selling and commissioning art pieces on my own
- studied my art sales history and realized I’m a better salesperson than I’ve given myself credit for
- also realized I’m underselling myself, spending more than I want to spend, making less than I ought to make, and a terrible negotiator
- realized I had unresolved feelings for a crush that didn’t want me back and took it more poorly than I’d like to admit
- decided that after a year of not trying for anything serious, I should force myself to start dating again
- signed up for online dating with some success; began analyzing these online social experiments of human interactions and realizing I’m mainly on OKCupid for the questionnaire and that little personality chart they generate for you
- faced my hatred of the dating game and went on a lot of dates, both good and shitty ones; didn’t worry about the end game
- met someone I liked a lot, deflected my feelings like a cop-out
- started training for the Tough Mudder
- began forgetting my Spanish
- went camping and enjoyed the Wisconsin summer to the fullest
- went to business workshops, some really good, some genuinely worthless
- started exploring the startup realm; to those of you who’ve drunken the Kool-Aid, I’m here to say, same shit, different place. It’s all the same highs and lows and problems and opportunities as any other type of work setting. That’s not to discourage anyone, but really, don’t buy the hype wherever you choose to go to make a difference. Just do good things, where you are, with what you have. And find people who are better than you, in different ways.
- questioned human progress
- met someone else I liked and dated him for two months; came to the mutual conclusion that we were good on paper, but not really right for each other
- was happy to have learned more about myself in the dating process, but wondered if I would feel that spark again
- reassured myself that I would feel that spark again and to be patient
- got asked to consult for a chemical company, a salon, an artist, other consultants, said no
- got asked to consult for a health clinic, said maybe
- got asked to consult for a software company, said yes
- learned that even though I chose that software company based on its values and vision, it still wasn’t the right fit; changed my yes to a no
- realized there are shit tons of consultants
- in general, got a lot better at saying no
- but also got worse at saying no; accidentally triple-booked myself on one occasion, was reminded of the saying, “If you try to please everyone, you’ll end up pleasing no one.”
- wondered if I might be unemployable
- got in a better habit of calling my mom; realized that she, too, was finally healing after my dad’s passing; saw her true personality come out, the one my dad must have fallen in love with; got to know her better and love her more deeply; began wondering why I have so many more dad stories than mom stories to share and how to change that
- read a shit ton of books, even for me (one of these days I’ll put together a favorites library)
- met one of my former bosses for lunch, told him I would have been a better employee had I known what I know now; made him laugh
- became super skeptical of coworking spaces after being invited to try one out. A phrase I’ve thought of often since quitting my job, per George Orwell, “Freedom is slavery.” Are we free, or are we just entering a different cage? Per Bob Dylan, “Everybody has to serve somebody.”
- was attacked at knifepoint near the Madison bike path; fortunately got away, but realized pretty quickly that, like most major things, it would go unresolved until something more serious happened
August 30th-present
- completed the Tough Mudder, which wasn’t that tough except for maybe a couple obstacles, but still a lot of fun. Do it with an awesome group of friends, don’t hesitate on the high jumps or the big moves, and remember to smile because they are taking your picture, or don’t smile if you know how to make fun of yourself.
- coming down from my endorphin high from the Tough Mudder, I checked my phone that night and saw an article about a woman who had just been raped on the bike path, a block from my own close call
- got super disillusioned, by survivor’s guilt, by people only rising to action after a catastrophe, by the media sensationalizing more than informing; decided if I didn’t want to become a part of the problem, I should speak up about it
- also felt encouraged by how good and responsive the Madison community is; seriously, we have some solid people here
- got interviewed by Wisconsin State Journal when they caught wind of my blog and Facebook post; thought they did a better job than WKOW
- still worried (and worry) about becoming part of the problem
- started trying to figure out how I can use my skill set to drive sustainable social change
- meanwhile, participated in Maker Faire Milwaukee and drove a steamroller to make giant woodblock prints
- applied for a grant to do a public art project for City of Madison; got the grant, now I need to figure out how to build two light sculptures as prototypes for something bigger :|
- also got interviewed by Channel 3000, who did a good job addressing community safety and asking what community members can do about it; also, for pointing out, hey, this guy still hasn’t been caught yet, this isn’t over just ’cause we’ve had some fundraisers
- since the summertime, went to four weddings and two funerals; thought about love and loss and what I might regret not pursuing; felt happy, felt sad, felt grateful for how many examples of strong relationships I now have in my adult life
- trying to figure out how to resolve my desire for a relationship with my disinterest in the dating scene
- rewrote my business plan and goals for the next year
- strategizing
- combatting imposter syndrome
- meeting and getting advice from people who are better at business than I am
- embracing what Nassim Nicholas Taleb said about a monthly salary being one of the most dangerous addictions
- wondering if we as a culture can surpass the charity mindset
- working on becoming a better teacher and making sure that education is always a part of what I do for and through work
- thinking and writing about paradigm shifts
- scared like you wouldn’t believe
Ten Important Lessons, of Many
- It’s hard not to feel pressured to live up to certain expectations. It’s hard not taking your ceiling with you. It’s hard saying no to things you don’t want. It’s hard saying yes to things you do want.
- When business is slow, it’s a good thing. Use that time to reflect and improve.
- While I’m a great go-getter, I’m a lousy get-it-doner. I make it to 90%, and then my perfectionism kicks in. I worked like mad to get my artist’s book, The Golden Cage, finished in three weeks. But even though it’s a childhood dream of mine to publish, I haven’t done it yet. Why? I’m not happy with the cover. I’m not happy with the text. People I show it to love the story, but I don’t think it’s good enough yet. I need to get over this, or else it’ll never happen.
- It’s okay to need other people. It’s okay to ask for help. To love others and let them love you, that’s the bravest you’ll ever be.
- It can be a very tit for tat world. Be mindful, not all reciprocity is good or for the right reasons. And sometimes, people reject each other, not because they don’t care, but are scared of what they have to lose, of being the one who cares more. Don’t be scared to be the one who cares more.
- The things you care about will hurt you. If you didn’t care, it wouldn’t hurt.
- You never know what the “by-products” of your actions might be. I quit my job because I knew in my heart, it wasn’t it. Suddenly, I had all this time. So what was a “by-product” I didn’t expect? A better relationship with my mom. I didn’t quit so that I would have time to get to know her, but because I quit, I finally did. If I got nothing else out of this past year, a closer and healthier relationship with my mom would have been enough.
- Embrace, acknowledge, and hone your strengths. That’s the only way you can use them for good and prevent them from being used for evil.
- Waiting isn’t always a waste. Just like the apple trees need winter to grow apples, learning when and how and on what to wait is important.
- Even though I’m a cat person, I have a dog personality. But I love people with cat personalities. Remember to surround yourself with people who are better than you, in different ways.
Three words that people keep calling me, and even more so in this past year than previous ones
- brave, which makes me wonder how people define bravery
- ballsy, which I hope you find as much humor in as I do
- unpredictable, despite being reliable
Three critiques I keep getting
- uncompromising for both better and worse
- independent to my own demise
- too nice, too forgiving
Whether you agree or not, it’s important to pay attention to the feedback people give you.
I wrote the following passage last year and feel it still holds true; it’s a worthy reminder I’ll need to come back to as I pursue my next set of goals.
“Some people have called me brave for being willing to quit without knowing what’s next, and others most definitely think I’m a reckless idiot. But if there’s anything I’ve learned, it’s to trust as much in the counterintuitive as we normally would the obvious or the sensible. To be in control requires a willingness to let go of control. To have stability and security requires that we not need either. To grow, we must always be questioning, always be listening, without needing to find the answers we are searching for.”
