Jobless: a guide on how to successfully be unemployed — Vol. 1

I did everything I was supposed to do.

In fact, I far exceeded and outpaced what I was supposed to do. More than I ever thought imaginable. Especially for some first-generation college, working-class, kid from Sheboygan, Wisconsin.

This is NOT a “how-to” guide to successfully being unemployed (this is Capitalism people — that’s not a real thing). This is actually the story of how a bachelor’s degree, master’s degree, a job at the White House, and the development of an amazingly successful program led to unemployment — with no job in sight — and how I’m dealing with that reality.

Being unemployed is hard. It’s especially difficult feeling like you have all the energy in the world to DO GOOD without a platform to do so. Like a performer without a stage.

It’s an apt analogy — because upon “leaving” my previous position at the global technology nonprofit Mozilla — I immediately fled to Los Angeles to take Storytelling courses at Upright Citizens Brigade (UCB) — an improv theatre co-founded by Amy Poehler (SNL, Parks & Rec).

Taking classes at an improv theatre was my dream as a teenager — ever since I was voted, “Most Likely to Join SNL” in high school. The Storytelling class, taught by national winner of “The Moth” story slam Margot Leitman(NPR listeners unite!), was an intensive course culminating in a public performance at the Upright Citizens Brigade theatre in Hollywood. As the only non-local, non-performer/actor/theatre person in the class, I felt like I brought a unique perspective.

UCB Storytelling Performance — Los Angeles, CA

What an amazing, life-changing, experience. We all have an interesting, unique background — but I had no idea how many stories I truly had until taking this course. My dream of improv was derailed for multiple reasons. Number one being the pressure to take the prototypical 4-year-college path directly out of high school.

Despite having deeply unique things happen in my life: working in The White House for Barack Obama, working with elephants deep within the Thai jungle, and meeting my dad for the first time on international television: none of those subjects were even broached in class. Instead — my stories consisted of funny predicaments growing up with my grandma being my best friend, funny mistakes from being a socially awkward teenager attempting to work in customer service, and attempting to come-of-age as a chubby video-game-loving nerd.

I highly recommend to anyone with a passion they put on the back-burner: it’s never too late. Go live your #dream. You won’t regret it.

I am now writing this story from Japan. Thanks to Scott’s Cheap Flights — I booked a $500 round-trip ticket on a whim to a country I’ve always been fascinated about due to my nerdy childhood involving Nintendo, Sega, anime, Pokemon, and one of my most-beloved books as a child: “Crazy Japanese Inventions”.

Writing this article from a parklet in Shinjuku, Tokyo, Japan.

I didn’t come to Japan because it’s luxurious. I’m not staying at a resort, or a spa — I’m sleeping in a drawer in a hostel for $8US a night. I came here to learn — about the culture and about myself.

A hall of “capsules”. #TubeLiving

Travel makes us think, it makes us more creative, and it definitely makes us more interesting. According to The Atlantic, “foreign experiences increase both cognitive flexibility and depth and integrativeness of thought, the ability to make deep connections between disparate forms.” I wouldn’t word it in that exact way — but I can tell you, I’d rather be writing this from this cafe in Kyoto:


…than sitting at home stressing about how I haven’t heard back from the hiring manager from a dozen jobs I’m in the process of interviewing with.

My friends who are currently unemployed have told me horror-stories about being promised “good news” only to be ghosted for the rest of eternity as they wait with anticipation on the “next steps”. Or, for an organization to “go with someone local” despite them being amazingly qualified and, basically, the perfect candidate (I thought this was the “gig economy”…is anyone really “local” anymore?). This happens at some of the most progressive, forward-thinking, organizations — but I also understand HR managers are dealing with a record-number of applications.

I think this issue boils down to the over-education of our workforce (the “I don’t know what to do with my life, better go get that Phd’ mindset) and the underrepresentation of actual unemployment figures (the United States feds claim to host 4.4% unemployment — but “underemployment” figures nearly double that figure for people who don’t work enough hours to get by, or for people who have simply given up looking for work out of hopelessness). I am of the group that believes “real unemployment” to be closer to 10–15%.

A good friend of mine who is hiring for a major tech company recently said to me, “we already received over 400 applications for this position, and I haven’t even looked at a single application from someone who isn’t currently employed yet”.

THAT’S INSANE. Not only are unemployed people battling with millions of other unemployed people for jobs — they also have to contend with (much more desirable) employed people who want to upgrade their current role or are looking for something fresh. As they say, “there’s never a better time to look for a new job than when you have a job” — but in this evolving economy it seems like everyone begins that job search the second their orientation at a new organization is complete.

Not to be an old fogey who stresses organization loyalty, but I constantly see articles suggesting, “you should always be looking for your next job”:


What kind of life is that, honestly? Constant FOMO and worrying (planning?) about the future is no way of living. You’ll end up at your grave, thinking for the first time, “Oh, now I can take a breath, and relax. The future is, finally, all figured out”. I agree in being a somewhat calculated-opportunistic-employable-entity — but to be on a constant search for the “next gig” is not only exhausting, it’s completely unfulfilling.

Don’t worry — I got a Japanese baseball game in. I witnessed the Yomuiri Giants defeat the Tokyo Yakult Swallows 4–0 (pitcher threw a no-hitter!)

Despite feeling very lonely (I’m over 5,000 miles from my nearest friend): I’m not going this entirely alone. I know many people out there are in the same predicament but are scared to speak up. Admitting to being unemployed, or seeking work, is a blemish that carries a large stigma. We see a rejection from the workplace as a rejection of our entire existence — and why shouldn’t we? We are filled with anxiety beginning in middle school (oftentimes earlier) to worry about our future careers — to figure out what color our “parachute” is. Then, once we finish our 20+ year educational investment, we are constantly asked, “So, what do you do?”. Like it or not, our careers define (a large part of) us. I wouldn’t be surprised if tomorrow I opened up my trusty thesaurus and saw “existential crisis” is now intertwined with “workweek” (actually, I suppose the weekend is the recovery period where we can actually contemplate our purposefulness — or lack thereof).

We see a rejection from the workplace as a rejection of our entire existence — and why shouldn’t we?

(spoiler: we really shouldn’t)

Being unemployed is hard. My job ended due to no fault of my own — I was managing a program called the “Gigabit Community Fund” for Mozilla. It was one of the most successful things I’ve ever witnessed or been a part of — it was my job to hand out money to people doing amazing community development/impact work each and every day. I used micro-impact-grants ($10–30,000) along with community events, meetups, and discussions to break down the silos between government, education, and technology to create sustainable transformative public benefit. I loved each and every day — it truly was a dream job.

Unfortunately — Mozilla decided to focus their efforts elsewhere and sunset the program (and it’s funding from National Science Foundation).

I was so immersed in the amazing work we were doing, and trying to soften the blow of the funding cut, that I wasn’t using my time to find my “next big thing”. So, when the time came, I was a bit unprepared. I wrongly assumed that due to my success, my accolades, and my resume that I would have no problem finding a fulfilling position that compensated me fairly and would allow me to have as much, or more (if possible), impact.

I was wrong — or at least overly-optimistic at how quickly it would happen. My skills, effort, or personality alone won’t guarantee me that dream job — and good things take time. I was just flown out to interview with an organization in DC who said I was in the final four, narrowed down from over 150 candidates (and god knows how many applications). The numbers game is not good — landing that ideal gig takes grit, effort, connections, but also (like it or not) a little luck.

So now I am left here — wondering:

“What’s next?”


...for you, I have chronicled all 46 days of my unemployment experience thus far. Through video blogs, through writings (such as this one), and more — all while taking storytelling classes in LA and traveling across Japan.

Hopefully someone can find this experience relatable, interesting, or even inspiring.

This article is titled, “Vol. 1” for a reason.

Vol. 2 is the success story. It starts with me getting a new role that I can throw all of my passion, skills, enthusiasm, and loyalty into. It ends…well hopefully it doesn’t end for quite some time. I look forward to bringing you along on my journey.

Not in a rush to find the next thing — hyper-literally in my zen space, waiting for the right opportunity.

If you want to help contribute to Vol. 2 (by sending me a job lead) feel free to look here:

Thanks for joining me & look out for Vol. 2 at a Medium/Linkedin near you soon…さらばだ

Craig Wiroll is a has-been reality television “star”, Asian elephant rehabilitator, waterfall repairman, two-time garlic eating champion, and also worked at Pizza Hut and The White House.

He lives alone with nobody — oftentimes out of the back of his Subaru. — attempting to arrange sentences in amusing ways since ‘87 • Peace Corps // Mozilla // White House (44) // AmeriCorps • Oregon ❤ Wisconsin

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