The Mid-Year Review
A professional post: Context Collapse #145
What’s been going on at work, January-August.
(Based on format from David Perell)
It’s August of 2022 already. LOLOMG this year’s gone quickly.
With that said, I’ve never actually written a mid-year review (two-thirds-of-the-year review?) before. David Perell did a pretty good job of writing his, and I thought that was a pretty good excuse for jumping into mine.
This is going to be a walkthrough of what’s been going on in my work life for the past eight months or so—running a consulting firm, working with clients, juggling work life and personal life and a whole bunch of other things.
Let’s do it.
Work Projects
Over at Ungerleider Works, the past year has been, well… pretty damned fun as far as work goes.
Our marquee projects for the past year included:
Cannes Lions award applications for a major technology brand and their advertising agency of record.
Writing LinkedIn thought leadership posts for a major consulting firm.
Research and question/storyline advice for a trade association’s B2B professional education podcast.
Editing white papers and ebooks for a venture capital firm’s portfolio companies.
As a cranky consultant from the journalism and advertising world who also happens to be running a small business (as any boutique agency is), it thrills me endlessly seeing the company thriving and picking up lots of work.
The one twist has been, of course, the economy! The current recession/recessionish? situation means that a couple of projects we were working on were scrapped and that our client pipeline took an unexpected hit this spring as the first bad news hit the advertising and tech worlds.
However, we had a surprising upside to this. The cutbacks and layoffs at many agencies meant an increasing interest in outsourcing writing and creative work to us—I mean, being able to write and edit content more affordably+effectively than our clients can in-house does have some advantages.
Now onwards to the behind the scenes stuff…
Restructuring The Business
I took a big step at the end of 2021 and shut down the S-Corporation under which I had been operating since 2014 (first freelance, then full-time) and opened a new business, Ungerleider Works, Inc. after the start of the new year.
Basically the gist is this: I started my old S-Corp when I lived in Los Angeles. I then moved to Chicago in 2018. Without getting in the weeds of tax stuff, this meant I was dealing with tax authorities in Los Angeles, California and Illinois! This meant lots of annoying compliance things that took time away from making money. My accountant recommended shuttering and reopening. I took his advice.
I also used the restructure as an excuse to grow from freelancer into agency. We’ve been taking on a lot of projects where we’ve been working with external graphic designers/web developers/video editors/etc. and the shift made sense. Rick Webb of the Barbarian Group’s excellent book Agency helped a lot with figuring out the nuts and bolts. So did a few 1:1s with agency operators who walked me through the whole scaling-from-full-time-freelancer-to-running-an-agency michegas. So far, so good.
I’ve been working with some great vendors and contractors who are handling things like bookkeeping, admin, marketing and creative. All of these are good things.
Down the line, I made the decision to run the business almost entirely on Notion with the exception of bookkeeping, payroll, CRM and to-do lists. Todoist has been great for to-do lists and Toggl for time tracking specifically.
I also made the decision to join a combination coworking space/social club in Chicago to use as my business’ headquarters. While working from home can be great, I found that having a seperate living space and working space—and setting clear boundaries between the two—was the best path for my business and myself. So far so good.
Learning Things
I made an intentional decision at the start of 2022: Read less non-work related online content, read more books and dedicate time to guided learning.
The good news: It’s been working.
I specifically decided to pay for two online courses.
The first is Corey Wilks’ Intentional Life Design. Wilks is a psychologist in Kentucky who recently made the transition from private practice to executive coaching; I found his course completely by accident in a Twitter rabbit hole when my sister was discussing some of the issues she faces in her therapy private practice (plug plug if anyone in NY needs an amazing therapist!). Anyway, he describes Intentional Life Design as a course on how to “Build a fulfilling life and business, without the bullshit.”
It worked 100% for that promise—and, specifically, for figuring out how to reconcile running a small business, being a parent and finding time for things I care about outside of work. The framework of having other students in class to collaborate on coursework with and accountability in set times for the class meant a lot. Check it out.
The second was a video archive of Ramit Sethi’s How To Talk To Anybody. While I like to think that my social skills are pretty good, the facts are the facts: I run my own company now and I’m doing all the client pitches and business development that my old companies had fancy sales and marketing people for. Salespeople who have specialized training in these things. Not to mention we just spent two years or so in a global pandemic starting at screens instead of other people! So a course on upping your small talk game, in this context = Gold.
I mentioned Agency earlier, and I’ve also been leaning a lot on YouTube tutorials for skill-picking-upping. Also learning Spanish, Portuguese, French, Hebrew & Yiddish on Duolingo for fun (Whew!). Which brings us to…
Handling The Hiccups
This year had some unexpected personal challenges. My mother died suddenly of acute leukemia in March several days after hospitalization, and both my father and stepfather were hospitalized in the following months. Nothing that anyone can do about it, so it goes.
My son is now 3 years old and has made amazing progress over the past six months. Seeing him pass developmental milestones and master things like potty training, independent play and even smart aleck conversations is an absolute joy. He attends preschool full-time; my wife works a senior-level role at an advertising agency while I run a consulting firm—juggling work and parenting is a constant project but one we’re both becoming better at.
Apart from family emergencies, work plans this year were also derailed by a few unexpected situations. We lost childcare for approximately 2 weeks in January due to a COVID outbreak. My wife, son and myself all got COVID later in the year. All of these meant unexpected time off from work when I had a new business to launch and eyes to keep on the ball.
There was a blessing to all the unexpected hiccups though: Realizing that I needed to build systems in my business so we could continue to serve clients at the same quality they’re used to, and scale to serve additional clients, even when I’m not in the office. This means building systems and frameworks so business doesn’t come to a standstill when there’s a personal emergency. That means…
Building Structures
Some of the things I’m proud of:
Finding the right Notion templates so day-to-day business management stuff isn’t a shambles of different web pages and apps.
Outsourcing work where it needs to be outsourced.
Streamlining our CRM so we know who we’re marketing to and how we’re marketing.
Creating checklists and routines for everything from onboarding new clients to writing blog posts to publishing YouTube videos for clients.
Personal Habits
I stopped drinking from July 2021 to February 2022 and lost 40 pounds in the process. Since then I’ve been intentionally focused on making drinking alcohol an occasional reward instead of a daily habit.
I built a fitness stack for myself of alternate days of running and Peloton, with weight training everyday. Of course, sticking to that damn fitness stack is an entirely separate project but one I’m trying my best at.
Bought both an Instant Pot and an air fryer, which have stolen so much damn time back in the kitchen and made cooking easier.
And reading books instead of doomscrolling the internet has been a stunning success—even if it meant rebuilding my attention span in the process.
I genuinely hope you enjoyed this look behind the scenes and that you found it useful in your own work and life projects.
That said, I’ll update this with a rest-of-year followup in December. See you then.