Field Notes / Whoever said happiness doesn’t come from a lack of problems wasn’t self-employed

Whoever said happiness doesn’t come from a lack of problems wasn’t self-employed

Last quarter was a mix of tough luck on the creative side, pipeline headaches on the business side, and unexpected expenses. Yay self-employment.

There’s a saying that happiness doesn’t come from a lack of problems, but from finding the solutions to your problems.

Whoever came up with that obviously wasn’t self-employed.

For the record: I like the grind. I like climbing mountains, metaphorically. I like proving to myself that I can solve difficult problems.

But there’s a difference between difficult problems and annoying problems.

Difficult problems give you a sense of achievement when you overcome them.

Annoying problems grind you down and distract you from what you should be doing. Sick days, daycare issues. That kind of thing.

Last quarter had no shortage of both.

[Aside: I asked AI to generate a picture of a stressed self-employed man in the style of a New Yorker cartoon to illustrate what the last 90 days have felt like, and here’s what it churned out.]

AI’s interpretation of me last quarter

Triggering. Very triggering.

Then I asked it to give me more muscles and it created this.

Me again, but more accurate. It’s like looking in the mirror.

Fantastic representation. No further notes.

Thirst-traps aside, here are the biggest problems I faced last quarter and how I’m thinking about tackling them. (Don’t get me wrong, it was a great quarter — but if all I do is brag about wins instead of highlight challenges and come up with a better game plan, then I’m wasting our time.)

Top 3 “Difficult” Problems

1. Building pipeline is hard

“Pipeline” is a fancy term for deals you’re actively working on. You want to make sure you have enough in the tank to hit your targets and not go broke.

Salespeople understand this deeply. It’s great to have a good quarter, but if you don’t have more leads / calls / steak dinners lined up for next quarter, you’re in for a bad time, especially the longer your sales cycle.

Since being self-employed, I haven’t had problems with pipeline — mainly because I work with channel partners with large sales teams that refer business to me and because my affiliate income is pretty stable.

Unfortunately, when you rely on channel partners, there’s always a chance those folks don’t hit their quotas and you’re left holding the bag — which is exactly what happened a month ago. Projects ground to a halt, referral deals fell through, and suddenly Q4 was looking quieter than a graveyard.

Instead of waiting to see if projects would fall from the sky, I went on the offensive. I put together this video and started cold emailing.

When pipeline dried up, I recorded this video and used it to start prospecting

Results have been good. I’ve got a handful of promising leads and 3 deals at the finish line. No signatures yet, but it’s only been 2 weeks. That said, I shouldn’t count my chickens before they hatch. Birds fly, fish swim, and deals fall through. I’ll sleep better when the Docusigns arrive.

2. Selling a book is hard

Beyond drumming up more agency projects, I’m still busting my butt trying to become the next King / Hendrix / take your pick of household horror name.

After finishing a new book in Q2, I was focused on finding a literary agent in Q3 who would shop it to publishers. This ate up most of July and August.

Getting an agent is notoriously painful and full of rejection. For every fifty “no”s you might get one “maybe”, followed by another fifty “no”s.

The following is pretty much what it feels like.

Another AI representation of me during querying season

The process itself goes something like this. . .

You assemble a query package consisting of a query letter, a synopsis, and a sample of the first few chapters. Then you research the bejeezus out of agents who would be a good fit and hope they’re open to queries. If they are, great. You send over your query, kiss it up to God, and pray that they ask for a “full” — aka the full manuscript.

In the last 90 days, my stats have been the following:

# of Queried Agents: 65
# of Rejections: 11 (17%)
# of Unresponsive Agents: 50 (77%)
# of Full Requests: 4 (6%)

Anecdotally, I’ve heard anything above a 5% request rate is solid, so I’ll take my 6%. What’s hard is staying patient. There’s a site that tracks response times, and many agents take 6+ months to get back to you. Part of me knows there’s a better way to snag their attention, but I’ve also heard doing anything outside the norm can backfire and get you automatically rejected. For now, I’ll play by their rules. If nothing happens by December, I’ll get creative and try experiments to stand out.

3. Work-life balance is hard, especially during summer

Q3 is crazy, particularly when you have two kids without daycare for two months and a wife who’s returning to school.

What I found most difficult was working in spurts. I’m a guy who likes to plug in for hours, but that luxury wasn’t always available, particularly when the two-year-old was having exorcism-level meltdowns.

I know I need to be more efficient and work faster and get over my fear of perfection, but not getting caught up with self-criticism, as Ian Fleming suggests so cavalierly, isn’t always easy.

Ian Fleming’s take on working fast and not getting caught up with self-criticism

Here’s what I’m going to do to eliminate distractions and improve productivity in Q4.

>> Change my phone to grayscale. A friend convinced me to change my phone to grayscale to reduce the temptation of checking social media. I’ve done it for a while and surprisingly it seems to help, so I’ll continue in Q4.

>> Put reading front and center. I’ve moved my reading apps to my Home Screen and set stricter deadlines to finish books.

>> Set more aggressive daily writing targets. Some writers are tortoises (Ryan Holiday, John August) and some are hares (Brandon Sanderson, Anne Rice). I’m a tortoise with hare aspirations. I figure the best way to write more is to. . . wait for it. . . write more. I’m going to double my daily target from 2,000 to 4,000 words during active writing days.

>> Experiment with three-minute networking for 30 days. Jesse Itzler has a way of networking in three-minute chunks called the “compliment, congratulate, and console” framework. Basically, you take 3 minutes every day to send a message to 3 people whom you compliment, congratulate, or console about something. Apparently, it helps network more efficiently, so I’ll give it a go.

By reducing distractions, setting more aggressive daily targets, and networking more efficiently with the 3-minute rule, the plan is to squeeze more juice out the day during the craziest quarter of all — Q4.

Top 3 “Annoying” Problems

1. Unexpected expenses suck

There’s no sugarcoating it. Last quarter was a kick in the coin purse.

On top of normal expenses, I knew there would be some big ones. Namely: a second car and my wife’s college tuition.

But then our pool filter had a heart attack. And Nicole’s laptop had a stroke. And our kitchen window, not wanting to be left out, decided to engage in some sort of self-mutilation and snap itself out of its casing, because I definitely didn’t reef on it that hard.

That’s, like, $50k going poof in 30 days, a lot of which was unexpected.

Basically what happened to my cash last quarter

Thankfully, we’re fortunate savings-wise. It did highlight, however, how important cashflow management is for the self-employed. When the shit hit the fan, I had ~$60k of receivables that weren’t due to be paid for 30 days. Plus, a good chunk of my $$ is tied up in private company stock that’s not liquid. So even though on paper things looked fine, I can’t say it didn’t make me cut back on pumpkin spice lattes for a few days.

My advice? Shorten your payment terms from net 30 to net 10, keep more cash on hand than you think you’ll need, and diversify illiquid equity when possible by staying on top of secondaries and keeping an ear to the ground with old colleagues. You never know when it’s gonna rain.

2. Covid (still) sucks

Not much to say here except the whole fam got Covid again and it knocked us out for a week. That’s 8% of the quarter right there. We got it from a cottage weekend with friends that turned out to be a superspreader (I think 10 of the 17 people got it??). I wouldn’t take the trip back, but still, it sucks to lose a week.

3. Not living near family sucks

Anyone raising kids far from family knows it’s the worst.

Both sets of parents are flights away. There’s no dropping the boys off at Nana & Pop-Pop’s or Grandma & Grandpa’s for the afternoon. No sleepovers, no last-minute babysitters. We’ve been in a crunch several times, and thankfully things have worked out, but who knows when our luck will end?

Why not move? Career reasons. Nicole is studying wine, and there’s only one teaching winery in Canada (Niagara College). We’ve planted our roots. We have our dream house, and we still see our families throughout the year, but man, that doesn’t make the distance suck less.

What's next?

Here’s my updated goal tracker for Q4 2023.

A lot of writing, a lot of reading. A lot of agency work to pay the bills while dogging it with literary agents. Nothing ground breaking.

Catch y’all in the New Year!


Pictures from the field this quarter

Things I was obsessed with this quarter

>> If Books Could Kill. Ever want a podcast that tears pop science authors a new one? Here you go. I’ve always said Gladwell is full of BS, but these guys explain why he’s BS so much more hilariously than me.

>> Barstool. I’m not a sports guy, but everything about Dave Portnoy and his cast of questionables over at Barstool Sports are like a slo-mo train wreck I can’t look away from. It’s like The Office if Michael Scott was a pizza fiend with a Boston Rob accent, and, instead of Pam and Jim, you’ve got more bromances than a Hangover movie. I guess it’s a guilty pleasure now?

>> Return to the Movies. After 3 years of not stepping inside a theater, I returned with a vengeance. Indiana Jones, Barbie, and Paw Patrol 🍿

>> David Remnick interviews. The editor of The New Yorker, David Remnick, might be appalled to see me using AI to mimic his magazine’s art in this blog post, but hopefully he’d be flattered to know I spent hours researching his career last quarter. I’m fascinated by prolific folks, and how anyone can read — let alone edit — every story in every issue of The New Yorker blows my mind. His secret seems to be that he’s good at maximizing every spare minute and has a low tolerance for anything that wastes time.

>> Bing Image Generator. In yet another move to stay shockingly relevant, Bing released its AI generator powered by OpenAI’s DALL·E 3. It’s amazing. I spent a good chunk of time using up my first batch of free credits.

>> ON BOOK: The Scripted Musical Process. Two of my improv heroes, Jess McKenna and Zach Reino, replaced their improvised musical podcast with a new series that’s following them as they create a scripted musical. If you like musicals, this is the best thing ever. If you hate musicals, it’s the worst.

>> John Williams Suite from Hook. By FAR the most watched (and rewatched and rewatched) video in my YouTube history from the past 90 days is this live recording of John Williams conducting the Suite from Hook with the Boston Symphony. Is Steven Spielberg himself ashamed of the film? Yes. Do I still love it more than Romeo loves Juliet? Also yes.

>> LK-99. I almost forgot about this one, maybe because I’m trying to subconsciously erase the disappointment. If you know, you know.

That’s it, that’s all. Catch you in another three months ✌️


Devon Hennig

Devon Hennig is a writer, marketer, and ex-game-show host. He quit his job as a software executive to make a go of it on his own. Follow along as he tries not to go broke.

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