Field Notes / Top 10 takeaways since I quit my job and went solo

Top 10 takeaways since I quit my job and went solo

It’s been a full year since I quit my job and went solo. Here are ten things I’ve learned along the way.

“I’ve been clean for over 25 years, so don’t hold it against me.”

That’s what James Patterson tells people when they ask about his career in marketing prior to becoming an author.

I’m a looong way from 25 years, but I’ve officially been self-employed for one year now. That’s, like, twelve full moons. Not bad, not baaad.

Rather than pat myself on the back, I thought I’d share 10 takeaways from what I’ve learned since going solo. Hopefully it’s helpful if you’re thinking about taking the plunge.

Top 10 takeaways since going solo

Takeaway #1: Separate “worry time” from “execution time”

When you work for yourself, you need to be a blackbelt in accountability — and the best accountability hack I’ve tried is called “worry time.”

Here’s how it works. At the start of every quarter, I carve out “worry time” to reflect on the previous 90 days and set goals for the next 90 days. I’ll set aside a day to retro the previous quarter and plan the next one. After that, I stop worrying and start executing. The key? I don’t allow myself to worry about tactics or goals again until next quarter.

Here’s Sam Parr explaining his version of the same thing.

Sam Parr explaining his version of “worry time.” We basically do the same thing.

Beautifully said, Sam. If you do nothing else from this post, try “worry time” or risk falling prey to your own doubts and distractions.

Takeaway #2: Make sure you are in control of your targets

I’ve found the most important part about setting goals is to break them down into targets that can be achieved WITHOUT relying on anyone else. 

In goal-setting terms, it’s about focusing on “leading indicators” instead of “lagging indicators.” I.E., You want to focus on metrics you can impact.

Here are examples of good targets vs. bad targets.

>> Bad target #1: Publish a book with a Big 4 publisher
>> Good target #1: Write a 90,000-word novel and query 100 agents

>> Bad target #2: Grow social media following by 50k
>> Good target #2: Post 100 TikTok videos and reply to every comment

>> Bad target #3: Earn $100,000 from consulting
>> Good target #3: Apply for 30 consulting projects and send 50 emails to personal network requesting introductions

In the examples above, the bad targets are bad because they’re out of your control. The good targets are IN your control. Most folks have problems setting these types of targets, so practice every quarter.

Takeaway #3: Work like a lion, not a cow

Naval Ravikant has a good analogy about working like a lion, not a cow.

Cows spend all day grazing in order to fill their four stomachs. Lions rest and conserve energy until a gazelle goes by, and then they strike, sprinting and devouring their food before resting again.

The typical 9-5 job is a cow’s work week. You do 40 hours, but you earn a fraction of the value as more successful people because of leverage.

Naval Ravikant explaining the concept of working like a lion instead of cow

This is why I decided last year to focus solely on five-figure consulting and analyst projects. There was a point where I was doing hourly calls for decent money (average $500/hr), but individual projects like that weren’t worth it in the long run, as they ate away at valuable hours that I could be using on higher-leverage activities.

Even though it’s more difficult to sign five-figure contracts than $500/hr calls, it allows me to make enough in one pop that I don’t have to constantly be worried about doing smaller projects — i.e., I’m able to work like a lion. Run, rest, run, rest. It’s also a big reason I was able to take 10 weeks of vacation last year and not feel stressed.

Takeaway #4: Build an army of salespeople you don’t have to pay

Here’s a lesson I learned at Vendasta: channel partners are a secret weapon.

The most valuable network you can build is an army of salespeople you don’t have to pay — particularly if sales isn’t your superpower. That’s exactly what I’ve done with my analyst projects. I’ve partnered with companies that refer me projects, so I’m able to focus on fulfillment and the creative parts I enjoy while they take care of sales. Win win.

Takeaway #5: Change your info diet

Shaan Puri says: “Pretend you want a six-pack. You need to start thinking and acting like someone who HAS a six-pack. Fit people travel with protein powder and resistance bands in their suitcase. They pick hotels based on the gym. They hang out with other fit people.”

Same goes for anyone who’s audacious enough to quit their job and become an entrepreneur. Unless your friends and family are entrepreneurs, they won’t get it. The best thing I’ve found for honing my mindset and staying motivated is to change my info diet and listen to others in my shoes.

Note: You don’t have to know these people in real life. Some of the best teachers are those you’ll never meet. Personally, my info diet consists of podcasts (My First Million, All In, Scriptnotes) and YouTube videos.

Takeaway #6: Watch sports documentaries

Here’s a random one. I’ve found it surprisingly motivating to watch sports documentaries even though I’m the farthest thing from an athlete. It’s inspiring to see how hard athletes work to get to the top of their game, and in solopreneurship where there is no scoreboard, it’s helpful to watch other people competing against themselves to be the best in the world.

Sports documentaries I recommend: Break Point, Full Swing, The Last Dance, and Tour de France: Unchained.

Sports docs I recommend on Netflix: Break Point, Full Swing, Tour de France: Unchained.

Takeaway #7: Look for 4D chess moves

A 4D chess move is a decision that seems counterintuitive or confusing at first, but in the long term proves to be valuable because it anticipated market changes, competitors’ actions, and other factors.

Two personal examples from last year:

1) Flipping a job interview into a pitch for a consulting partnership;

2) Inviting a prospect onto a podcast to build rapport before attempting to make a sale.

It’s not about being manipulative; it’s about keeping your eyes open for opportunities to reframe an interaction and maximize value from a relationship. The two examples above are exactly how I was able to close several big opportunities last year.

Takeaway #8: Take “Atomic Habits” seriously

If you’ve never heard of Atomic Habits, watch the following video (or better yet, buy the book) and then put it into practice as fast as you can.

“You do not rise to the level of your goals. You fall to the level of your systems.”

A few Atomic Habits I’ve adopted that I find valuable:

>> Create a physical checklist for daily goals and hang it in your workspace. When you physically have to cross something out every day, skipping a day will feel like sacrilege. Helps maintain accountability.

>> Put clothes out the night before. My brain is mush in the morning, so having my outfit ready to go is great.

>> Clean baby bottles and have them ready with formula the night before. See previous bullet about brain being mush in the morning.

>> Carry a physical book around. One of my ongoing goals is to read more, and I’ve found I’ll do it if I have a physical book instead of a digital copy. Too many distractions on a phone or tablet.

Simple tweaks like these have made a big difference in hitting my goals.

Takeaway #9: Your network is more valuable than you think

I saw someone on LinkedIn say that most people are so worried about marketing to strangers that they neglect to leverage their own network.

So I sat down and went through all my LinkedIn contacts —

And holy crap. You know what? The person was right. I was able to make a list of 50+ people I know well enough to reach out to and ask for intros or to pitch services to, and it’s turning out great. Cold emailing works, but warm emailing is where it’s at.

Takeaway #10: Try quarterly “offsites” with your partner

OK, so I haven’t done this yet but I want to.

If you’re in a relationship — and especially if you have kids — book a weekend away where you and your partner escape your daily routine to do an “offsite”. Go somewhere fun and take time to review your goals, your finances, your relationship — whatever.

It’s easy to get caught up in the grind and forget to talk about the big stuff with the person who matters most. Does a “spousal offsite” sound cringey? Yes, but so do corporate offsites, and you know what? People come back feeling recharged and motivated. Don’t knock it till you try it.

Goodbye year one, hello year two

Before I wrap up, I have one more thing to share.

I saw this post on Twitter where @gregisenberg listed a ton of things he was thankful for as a solo founder. Every item made me nod and smile.

There’s no better way to sum up how I feel a year into this. Long story short, I’m #self-employed-strong. Here’s to the next year and beyond.


Pictures from the field this quarter

Things I was obsessed with this quarter

>> Music documentaries. Netflix dumped a boatload of music documentaries on me and I was all over it. The ones I recommend are Biggie: I Got a Story to Tell, Clive Davis: The Soundtrack of Our Lives, American Masters: Inventing David Geffen, Can’t Stop, Won’t Stop: A Bad Boy Story, Hip-Hop Evolution, Rapture: LOGIC, and Like a Rolling Stone: The Life & Times of Ben Fong-Torres

>> Shows with compelling people. In addition to music docs, I enjoyed Anna Nicole Smith: You Don’t Know Me, King of Collectibles: The Goldin Touch, and Stan Lee. (All of these, by the way, I was able to watch before breakfast while feeding and entertaining my six-month-old over the course of the quarter. My kind of multitasking.)

>> John Grisham (cont’d). I continued my John Grisham streak by completing the Jake Brigance trilogy and watching a ton of Grisham interviews on YouTube. I particularly love the oldies like this one and this one.

>> Pearl Morissette. For my wife’s birthday, I booked reservations at Pearl Morissette — and it lived up to the hype as one of Canada’s top 5 restaurants. The food was phenomenal, and they spoiled us with the wine pairing, pouring extra samples when they found out Nicole was studying wine making. The server even sneaked us into the cellar while we waited for our Uber to sample more wine. Can’t get better service than that.

>> Southbrook. Another of our favorite Niagara wineries, Southbrook, started hosting vineyard tours this quarter with its always-entertaining owner, Bill Redelmeier. Naturally, we left our children with Nana and Pop Pop to do it. Five stars. Bill is the best in the biz, bringing along a backpack of wine and no shortage of stories. I think it was supposed to be an hour tour and it ended up being two-and-a-half hours. Time flew, wine flowed. If you’re in the area, this is a must for winos.

>> Querying. I finished writing my new book this quarter (yay), which meant the next step was starting the long process of querying literary agents. Since I’ve only ever self-published, there was a lot to learn re: query letters, QueryTracker, samples, etc. Much more on that next update.

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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