Geography Can Shape Opporunity

Having spent the last half-decade of my life in New York City, rural Pennslyvania (Danville), and now a small Midwestern city (Fort Wayne); I’ve been fortunate to experince nearly the full gamut of American life (at least at this latitude).

Today, I finally read the transcript of Joe Biden’s speech almost a year ago at Northwestern University. I think he understands the regional divide in America better than anyone with his platform.

So many people take a negative view towards the half of the populace that doesn’t live near them, not taking the time to understand how their life experiences led them to where they are. I deeply appreciate Biden’s optimism and share it in addition to the fact that he’s contributing specifc, actionable ideas as solutions.

I’m proud to be working in tech in middle America instead of in the VC hubs. I like knowing I’m contributing to the solution instead of furthering the problem.

1026 West Berry Street

Photo of Exhibition Entrance

I stopped by the 1026 West Berry Street: The Fort Wayne Art School exhibition at the Fort Wayne Museum of Art yesterday. It was interesting to learn about the history of art education in my new hometown.

It definitely caused me to reminess of my days at 1700 Lida Street.

Even though it was extremely hard and I work as a developer mostly now, I’m still really glad I studied graphic design at an art school and went through all the foundational classes which that entailed.

It taught me how to create, communicate and execute which remain the core of everything I do and both a developer and business owner. Obviously, those are things you should learn in any program, but I contend that there is something unique about learning design for developing those skills.

Plan Your Year

2019 is the first year in a long while that I could describe as “open ended” on January 1st.

We have no intention to move, no travels planned, and have gotten through a lot of the initial time intensive tasks of relocating.

I went through the Plan Your Year workbook put out by the people behind The Focus Course. Conventiently, I completed a lot of the pages while I was back in Pennsylvania meeting with Joel to discuss the what we want Grid & Arrow to accomplish this year.

The apex of the workbook is writing out your “2019 in One Sentence”; because I think it’s easier to hold yourself to these kinds of things if you make them public, here’s mine:

This year I am focusing on transforming how my businesses generate revenue while creating a home and routine in Fort Wayne that my family can thrive in.

The added clarity of meeting with my business partner in-person and going through the workbook gave me has me really excited about this year even though a lot of the things that I have traditionaly looked forward to (big travel, transition, etc) aren’t on the calendar yet.

I’m excited to write more about what I plan to create and be a part of as the year goes on.

→ Sponsorships

In time for Giving Tuesday last year, Grid & Arrow rolled out a WordPress Multisite network that’s all configured for organizations to manage their sponsorships programs. We have one organization in our pilot program so far and I’m excited about the potential this might have.

I wrote in more detail about the why and how of setting it up over on its blog.

→ Year in Review

Two firsts for me at the end of 2017 all in the same email:

  1. I sent out a company newsletter.
  2. I wrote a year in review.

After completing it, I felt like it was a really beneficial writing excercise for me personally and I hope my readers gained some value out of it too.

→ About South Sudan

A few years back in internet history, there was a great informational website about South Sudan located at, which we linked to from In Deed And Truth’s website. I was checking outbound links on their site earlier this year and I noticed that the site had been taken down and the domain was for sale; so I scooped up the domain and decided to launch my own version at the same URL.

I’ve got a lot of ideas about what this website could be, but for today, I’ve launched a minimal version that includes a basic history of the country, a feed of news articles, and links to books to read to learn more. Go check out the site or look at the source code on GitHub (it’s built on Jekyll).

→ Introducing Grid & Arrow

Grid & Arrow Logo

In my last post, I alluded to a business that I was in the process of starting. Today, I’m excited to publicly announce Grid & Arrow, a joint venture between myself and fellow Central Pennsylvania developer Joel Peterson.

Since my wife and I left Brooklyn in mid-2015, a sizeable percentage of my work had been hourly contract work for one company that I had no equity in. While I really enjoyed the work, if I’m being entirely honest, the looming thought of how many billable hours I completed in a week and my income being 100% tied to that had started to wear on me.

Concurrently, I had noticed time and time again that my business’ entire pricing structure was based on me getting medium to large budget jobs; I had nothing that I could offer to a low budget client without losing money myself. As I’ve gotten more involved with the small business community in Pennsylvania, I’ve been wanting to work less in California and New York and more in my own community, but have struggled to make the switch because of my pricing structure.

When Joel approach me about starting a hosting company after experiencing some of the same things, I realized we could craft a business model that had the potential to resolve both of the above.

We could build websites for a low upfront cost, especially since so many local businesses simply need a modern brochure-style website to present themselves well digitally, and make up for the time investment in the residual income of the monthly hosting fees.

After discussing the shared experience of building out advanced WordPress admin customizations only to have our clients just call us to have a change made, we decided that our primary offering would be “turn-key web hosting”, making basic changes to our customer’s sites just an email or a phone call away.

It solves a need many businesses have and, with a baby on the way, the idea of not all of my working time being devoted to “deep work” but supporting business with smaller tasks seemed like a wise transition for me.

As Grid & Arrow grows its legs, Joel and I will be continuing to operate our individual freelance businesses with full force for the foreseeable future (hire me, I’m looking for new clients). We’re excited about this new venture (and we have some other crazy ideas that extend beyond hosting) and hope you’ll check out the website we launched this week.

How I Applied Do Over

Cover of Do Over

At the beginning of 2014, I found myself in what Jon Acuff calls a “career bump”, a negative involuntary career transition. The agency I had been on a full-time freelance retainer with for the previous two years lost their largest client and suddenly had a lot less work for me.

As it goes, this didn’t happen at the best time either. Stefanie and I had had moved to Brooklyn eight months earlier and were struggling financially with the cost of living adjustment we’d made moving back to the United States (to the most expensive city in the country, no less).

One of the beauties of freelancing is that employment isn’t a boolean, you’re less likely to go from 100% employment to 0. This gave me a longer runway as I was able to continue to work part-time for the agency as I sought new opportunities.

One of the main reasons we decided to move to Brooklyn instead of one of the other options Stefanie’s medical school presented was that if this exact scenario presented itself, it would be a lot easier for me to find work; and in the end, that did prove to be true, but I made things a lot harder for myself. I vowed never to put myself in that situation again.

The Career Savings Account

From the second I picked up Do Over, Acuff’s concept of a “career savings account” immediately made everything I’d experienced click and gave me a tangible framework for how I continue to work to make my next career transitions better ones.

In 2014, my career savings account was almost empty, the rest of this post is about how I translated Acuff’s advice into my own life.


When I started looking for new work, it suddenly became very clear to me that my entire professional network was in southern California. Aside from some remote opportunities, this was less than helpful in New York. Every opportunity I replied to I had to do so completely cold, no one knew me from Adam.

The first step here was obvious, attend some meetups. Fortunately, there is nowhere quite like Manhattan for meetups. The sheer number of people who are below 59th Street at 5pm makes organizing something that 30 people will show up for on a weeknight less of an obstacle to overcome than it is elsewhere. As a result, there’s no lack of events to attend and introduce yourself to others in your industry.

After my employment situation was stabilized, I took the next step. I realized there were so many companies and organizations across the country doing great work who I followed online but I didn’t know anyone that actually worked there. I wanted to change that.

After some research, I landed on Circles Conference being the place I could go to meet as many of the aforementioned people in one place as possible. The experience was even better than I could have hoped for. I met more like minded people in my industry in two days than I had in the past several years combined.

I returned for Circles Conference the following year and will attend my 3rd Squares Conference (its sister conference) this month. Resisting the temptation to go to a new event each year and returning to invest more in the relationships I’d started (while still meeting some new people, of course) has been worthwhile.

When I left Brooklyn and moved to central Pennsylvania, I knew that I was going to have to be more intentional about all of this. There wasn’t going to be dozens of meetups every week on the path of my commute home. It took me several months, but I joined a local coworking jelly of other remote workers and made trips to Illinois, California, Ohio, and Ontario to meet in person with clients and other people in my professional network.

Skills & Hustle

These are separate sections in the book and you rely on them in different career transitions, but personally, my investment in both of these happens at the same time.

Every week I read about new techs from links posted on Twitter and I come up with ideas for side projects that utilize them.

In my day-to-day working, I often get stuck in execution mode, I rely on the the methods I know and only make progress on the most directly pressing work. During the periods I’m freelancing full-time, this comes with an extra sense of guilt, as I’m theoretically in complete control of my schedule.

I’ve developed a few strategies that help make sure I’m making progress on learning new skills and hustling on side projects.

For learning new skills, I’ve had a subscription to Code School ever since I moved to Pennsylvania. Their courses are broken into tiny subsections, making it easy to push myself to work for a few extra minutes at the end of the day to make some progress.

As for using what I’ve learned, I’ve found I have to follow the same strategy that I have with the courses.

I’m a proponent of the maker’s schedule, but the reality is I’m far less likely to get four or six uninterrupted hours to work on a side project like I do on my main paying client’s projects.

If I’m ever going to make any progress on a side project, I need to make a plan and divide it into as many small tasks as possible so I can do a little each day.


This section ended up being a lot more convicting than I was expecting from a book of this genre. Acuff writes that character is what you must invest in order to make a successful career jump, a positive voluntary career transition.

A few pages were dedicated to the negative patterns we repeat as we move from job-to-job and how they are like weeds that prevent your character from growing.

The negative pattern I repeat is that I consistently don’t complete work when I communicate that I am going to complete it.

While I continue to struggle with this, I am making progress by identifying the two causes of it – poor estimation and lax scheduling.

The root of my poor estimation comes from not valuing what I do and what I contribute enough. I minimize all the time I spend finessing over small details. I ignore that I like to step away from something for a few days and come back and change it drastically for the better. I make estimates based on the path to the final product being a direct one, which isn’t how I work nor a representation of the value I am capable of contributing.

My lax scheduling is a pattern that I’ve been letting establish since college, but it’s gotten worse since we moved to Pennsylvania. Our time here started with a lot of disruptions to my working time and space – we had a puppy running around and work being done on the house we just bought – and I let being disrupted become the norm even after the puppy grew up and the house was mostly finished.

If I correctly estimate that something is going to take 32 hours and I want to complete it in eight business days, I need to work on it for 4 hours a day. It’s simple math.

If I don’t spend 4 hours on day 1, I need to actively adjust schedules and/or expectations instead of my patterned behavior of being lax and just assuming everything will just be fine. It might all be fine, but I will not finish when I said I would.

Being proactive here has been challenging, it does not come easily to me; but when I look back at how I operated a few years ago and compare it to now, I can see that I have made progress.

Today’s Career Transition

Today, I find myself in a weird mix of another negative involuntary career transition and a positive voluntary career transition. My largest client was acquired at the end of 2016 and they’ve phased me out as part of the acquisition. While that was all happening, I started a business with a colleague where we’ll be using the skills we put to use in our individual freelance practices to create a business with an entirely different revenue model (something I’ll post about separately).

While transitions are always uncomfortable and require a lot of faith, I feel much more prepared today than I did in 2014.

Whether you’re going through a career transition right now or expect to go through one some day (hint: that’s everyone), I highly recommend picking up a copy of Do Over. It’s now available on paperback.