That’s 6000+ days of my life dedicated to working for one company. My previously longest-held job before that was a year and a half, just for some perspective.

This story is going to be a bit lengthy and I’m not trying to write a tomb of a post about it right now — so let’s start small and hope that I’m motivated to keep writing about my experiences — because I think they’re worth sharing.

There’s going to be a good bit to cover — why I stayed at one place so long, how I made the decision to leave, what I did wrong in that process, what it was like interviewing, putting together a portfolio, and how I came to choose the company that I’m now working for.

I’ll start with the good parts of my previous role and what finally convinced me to get out in pursuit of better opportunities.

I loved my job

My job paid well, gave me the freedom to work on what I wanted to work on and to take any approach that I felt would be of value. Over that 16 years, unlike many of my coworkers, I was able to stare at the ceiling and ponder ideas, facilitate rooms of amazingly smart people to help solve problems and to spend my time working with creative people designing solutions that were unique, innovative, and most importantly — viable in old and new markets.

It was fun, oftentimes exciting, and gave me a balance between my professional and personal life.

Deep work

Siloette of a bird sitting on a branch in front of a sunset.
Photo by lensmatter via Flickr

Last year, at some point during quarantine— I was given enough breathing room in my life to realize where my strengths were and where I wanted to go in my career. I talked about the newfound skills that I discovered in a remote working environment, wrote about not wanting to give up deep, focused work just to go back into the office, and told every one of my bosses that if the opportunity came up to be completely remote going forward, that I would jump on that chance. I was hopeful that they wouldn’t have a problem with me going remote-only.

I was wrong.

My pleas for going remote-only

A boxer dog sitting int he grass looking so so sad.
Photo by cuatrok77 via Flickr

I told everyone — The creative director, the head of design, the CFO, and the CEO. The higher-ups understood, but middle management just wasn’t on board.

So instead, I was asked to start going back into the office. in July it was one day a week, in November it was two.

Instead of embracing a culture that succeeded so well in a remote-only workplace, my bosses were convinced that collaboration and innovation were better suited to be done together in rooms with print-outs and sticky notes when we had already proved the opposite.

The impasse

A close up of a wall panted pink with spackle filling in a large crack.
Photo by Sergio Sánchez via Flickr

In much of my career, I had felt like my voice mattered but, with this, there was no getting through.

I had contemplated leaving many times in the past for many different reasons, but that was the last I could take. I had to part ways and there was only one thing that they could have offered to convince me to stay — Not the pay raise, not the extra bonus, not the promise to lead larger teams — but the ability to work on my terms from my home office.

And that offer never came.

What’s next?

Spoiler alert — I am currently working at a new job that is completely remote with an amazing team, an opportunity to grow my skills, and doing work that will make an impact. I couldn’t be much happier.

One of my goals this year is to get back into writing more. Much more. I have a lot to say about how I got here.

in business user-experience

When I got word that the FDA had approved and were starting to distribute the COVID-19 vaccine, I should have been a little happier about it - people are dying, struggling to pay their bills, and/or dealing with mental health.

I hope this vaccine will help prevent the deaths of more people and will get businesses (especially small ones) back up and running. I do.

But, selfishly, I was a bit disappointed that I have to think about transitioning back into a routine that includes going back into an office every day (or more than I am now). I love my coworkers and I love the work that we do, but I’ve had a lot of time to reflect on how remote work has complexly changed the way we work and interact with each other - and it has been almost all for the better.

I’m not going to go fully into the details here, but there are several things that I’m going to have a hard time adjusting to when going back into the office.

The amount of distractions

A time-lapsed photo of several dozen people walking up and down stairs. Its a bit blurry.
This is mentally how it feels working in an open office.

I work in an open office environment, which means that most days that I’m not sitting through meetings I will sit at my desk with headphones on trying to block out all the disruptions that happen during the day. Sometimes I do it to myself - I’ll hear a coworker talking about a project and want to chime in. Other times, people will ignore the fact that I have headphones on and walk up to my desk and knock on it like it’s a front door. I’m guilty of doing the same thing to people.

I’m much less distracted at home.

The ability to facilitate workshops

A close up of a large sheet of paper board with markers.
Ahh. Sticky notes, markers, and oversized sheets of paper. That’s how you know ideas are being created.

Quickly into transitioning to remote work I adopted Mural - an amazing app for holding remote facilitation sessions. Helping teams collaborate more efficiently and pull out new ideas is one of my favorite parts of what I do for a living.

Facilitation complexly online has had some benefits that I didn’t see during in-person sessions. For instance, I was doing a workshop on goals and asked the participants to start writing out their goals onto sticky notes. One of the participants was coming up with some that were a little too broad.

In an in-person session, even though I would have walked around to help coach ideas out of everyone, I may not have noticed the need to step in until after we had started sharing the ideas with the larger group - not great if we’re trying to generate as many ideas as possible.

In the remote facilitation session, I was able to see each idea as they were created and was able to chime in quickly to help get that participant generating more detailed goals - adding more value to the workshop.

Facilitating remotely gives you a gods-eye-view that you just can’t match in-person.

Keeping up with documentation

Two very large stacks of papers side by side.
The last set of functional requirements that I had to make.

I loathe documentation. Or, at least, I thought I did. I never made meeting notes and assumed (because we are all grown-ups) that anyone that was given something to take away and work on, would do that without prompt (and they usually do).

Out of necessity with this new environment and the fact that I could type notes while attending meetings (I used to just bring a notebook and rarely ever revisited those notes in details), I’m consistently sending notes, keeping better track of my tasks, and thanks to our sessions now being on Mural, we have more of a written record of our collaboration than we’ve ever had before.

When I do go back in, I’m going to need to bring my laptop everywhere I go.

Diving into deep work

Looking down a cylindrical pit made of glass with offices on the other side.
You thought I was going to put a picture of someone diving here, didn’t you?

It is so important to have the time and space to think deeply about problems and to research new ideas, methods, and processes. During the last 9 months, I have been able to adopt a better system for managing my knowledge and to turn off the distractions that I would normally receive in the office.

I feel more productive than ever. I am doing my best work and I’m more inspired about the work that I’m doing than I ever have been.

Going back into the office, although armed with new techniques for managing chaos, will bring my levels of deep work back to nearly non-existent if I’m not careful. I’m not looking forward to that.

Dreading the transition back

Several magazines, a phone, and a coffee cup sitting on a couch cushion
This isn’t a bad setup for a remote work environment. Coffee, magazines and a hipster pillow — what else would you need?

I’m pretty sure I can convince my higher-ups to let me stay remote indefinitely, but I’m certain, as a team, we will never be as productive as we are right now. I think back to those meetings where just a couple of people are dialing in on a phone and how difficult it is collaborating when some part of the team is at home and some are in the office. The people at home often missed out on conversations whether that was because of the noise in conference rooms or missing out on impromptu meetings.

It just doesn’t work. That will leave us having to adopt remote-first collaboration even when in the office - connecting to video calls when another participant is sitting just 6 feet away.

I’m not sure how well that will go over culturally.

It’s hard not to see the value that this experience has brought. It looks like we’ll just have to look closer at how we can adapt what has worked for us once we go back in.

I can’t speak for the rest of my coworkers, but I can’t wait to do that from the comfort of my couch.

in business productivity

An old payphone that is spray-painted pink with grafitti and stickers all over it.
This is not the phone I used. Photo by Cameron Rainey

I’ve never worked in sales, so I’ve never had to cold-call anyone before. Being on the other side of a telemarketer phone call, I had a perception of how terrible those people are and questioned how that strategy ever worked - except for scamming old people. I was never going to fall for a cold call and wondered why they ever bothered trying. I just assumed everyone handled cold calls the same way I did - by slamming down the phone while yelling “stop calling me!”

But, one day it dawned on me. I was a tad desperate after one of my largest clients was putting their business on hold — which meant I needed to land some new clients real fast, or I might not be able to eat after a few weeks - not to mention rent.

I thought to myself, “Everyone needs a designer, how do I get in front of them before someone else does?”" I thought back to the time I was working as an on-site graphic designer at a print shop in Philadelphia and how all kinds of random people would show up looking for small projects that they “needed yesterday” and how we sometimes had to turn away people because they expected us to be able to turn around ridiculous projects while they waited. I didn’t particularly like working in a print shop, but I didn’t mind working on small rush jobs. I wondered how other companies handled those situations and that’s when it hit me. I should just start calling people.

Writing down the goals

So I wrote down a small script (a habit and skill that now comes in handy when doing facilitation and research). My goal was to:

  1. Validate that other small print shops had the same outlandish requests with little turn-around time from clients.
  2. Empathize with their situation. (Having to turn away clients)
  3. See if they already had on-site graphic designers.
  4. Let them know that I could help accommodate those situations after-hours in extreme cases.
  5. Offer a rate that was a balance between them being able to make a profit and me being able to eat.
  6. Arrange a meeting.

Mentally preparing

A man sitting at a kitchen table with his hand over his face looking riddled with anxiety.
This guy looks as stressed as I was. Photo by Andrew Neel

I probably wouldn’t recommend this approach to everyone, but if you have a unique experience and an understanding of where you can add value, you just need a clear pitch and some persistence. I didn’t think I would be particularly comfortable in this type of situation, but I felt pretty good about what I was bringing to the table:

  1. I knew the situation that they often found themselves in.
  2. I had a quick and easy pitch - I wasn’t looking for a job. I just wanted to help out in certain situations.
  3. I was mentally prepared for rejection.

The first cold-call

So after feeling a bit more comfortable about what I was about to put myself through, I googled every print shop in the city and came up with about 20 places that were within a short subway ride. After a few deep breaths and maybe an hour or two of pacing around my apartment, I started calling those numbers.

I stumbled through my first call. I should have practiced my pitch before jumping right in, but the person on the other end was quite pleasant. They told me about a client that had come in that day and was asking for 12 posters for an event that next day and they had to throw all their resources at it - probably needing to work an extra hour after close to pull it off. They were used to that kind of work. I offered to “stop by when I was in the neighborhood to check out the place” and I was welcomed with the caveat that they probably didn’t need my help.

I was able to say that this first cold-call was successful and I did stop in the next day to talk about what unique services they offered and shoot-the-shit over their new Canon IR printer. But I didn’t even get a callback.

It wasn’t as dreadful as I made it out to be in my head

Sure, most of my calls were flat-out rejections but all of them were surprisingly receptive, open, and willing to talk about their business - something I wasn’t expecting. Not one of them said not to bother stopping in to say hi - I was hoping once they met me in person and I laid on my awkward charm, they’d have a hard time saying no. That proved to be a little tougher than I anticipated - I guess I’m not as charming or as irresistible as I believed I was.

The one that worked out

While I was mentally prepared for rejection, I wasn’t prepared for a 12-year-old kid answering the phone at one particular shop. He said, “My Dad is kind of busy, did you just want to come in and talk to him - he’s here all week every morning until about lunch.” I didn’t get a chance to even make my pitch. I’m not even sure the kid knew what a graphic designer was, but I added it to my list of places to stop into.

A half-dozen brochures sitting on the floor.
Some strewn printouts on a floor seems apropos. Photo by Henry & Co.

I spent the next couple of days visiting all the shops that I had on my list - believing that I could build a nice rapport and eventually land some business.

On the third day of hustling my services, I went to the shop where the kid answered the phone. It was a little far out of my way but like most of the places I went to in the city, I walked to save money. I thought it was a good idea - 30 blocks seemed alright. I’d done it before, except this time I did it in a suit. In the dead of summer. 90-degree heat, but I was prepared and made sure to pack some paper towels to wipe the sweat. I was very determined not to spend the $2 sub fare.

I went in, did some quick introductions, had a pleasant conversation about how they got into the business and how they were still figuring it all out. I made my pitch and unsurprisingly, the response was “Yeah, we get crazy people in ever so often coming in 10 min before close hoping to have some miracle done by next morning.” I said how aware I was and that because I was a night owl, it wasn’t a big deal for me to pull together something." Like all the other shops, I had a pleasant visit and I gave them my card and was clear to call me if they needed me.

It only took two days for the first call back from them. I got a call at 4:15 and the owner asked if I was still available. He joked that he was charging the client 3x his usual rate for the rush so that he could afford to pay me. We chatted briefly about the project but I can’t even recall what it was. I played it cool, but I was starving and agreed. He sent me an email and I was off.

At midnight I had already sent him my designs and by 9 am that next morning I had was on the phone to discuss. He was overly thrilled. Why?

  1. I lived up to the promise I made. I could pull off a miracle overnight.
  2. I gave him them a little extra - at no charge - to demonstrate my abilities and entice them to call me again.

I told him how glad I was to help out and reiterated that it was no big deal for me and that I was around at the drop-of-a-hat if they needed me.

Recurring work

The next day, the owner called me again with another request. He was right about having a lot of unreasonable clients. The jobs continued to pour in nearly every evening for another couple of weeks until he asked if I would be interested, at all, in coming into the offices and being available for a few hours a day.

Two people working at a table. One has a sharpie in their hand ready to write down ideas. The other is cutting up a printout.
Sharpies and scissors. What else would you need in a print shop? Photo by

I didn’t mind. I went in when I felt like it and they were all so welcoming. The operation consisted of a husband and wife who had only opened up the shop a year earlier - both of them worked there almost every day and often had their 2 kids helping out. There was another guy who knew how to operate the 4-color press, but it was very much a family business.

I tried to instill as much knowledge as I could on them about my process and my experience with printing. While I kept coming back because of the consistent, varying work, I made sure to take the subway.

Moving on

After about 6 months I had to give up the work. I started working nearly full time for a startup and just couldn’t commit any longer. I offered to help find a potential replacement and helped to onboard them.

That was a tough place to move on from. I’ve never been great at “breaking-up” with jobs and this one was particularly tricky. I got to know the owners and their kids over that summer and it felt like family there. For several years following, anytime I was in South Philly, I would stop in to say hi and was always greeted with a “Hey it’s Brad, tell us what cool work you’re up to.” I hope I made an impression on them because I’m still thinking about them many years later.

Make your calls but establish relationships

Cold-calling isn’t about trying to find a job or getting someone to buy your product - it’s about taking the first step to creating a mutually beneficial relationship. Some people won’t find that it benefits them and that’s okay, it probably wouldn’t have been beneficial for you either.

Four peoples hands stacked on top of each other like they're about to shout 'Go Team'. One of them has a cool tattoo.
What followed was a hearty "Go Team!" Also, that's not a bad tattoo. Photo by fauxels

Just like asking someone out, the first steps are a little shaky - but don’t let that stop you.

  1. Don’t fear being rejected. Plenty of people and opportunities won’t connect with you or what you’re offering at that exact moment. There will be other people and valuable connections to be made.
  2. Have a rough script and practice what you’ll say. To this day I write scripts even if I only follow them roughly. Be natural, and use it as an outline for every talking point that you have.
  3. Keep good notes of their responses. Use a CRM like Salesforce or Zoho - you’re going to want to follow up with people, be it in a couple of days or a few months. Make note of their responses (did they validate your goals), their sentiment toward your pitch (cold, neutral, warm), and make sure to set a date for a follow-up. If something isn’t going to happen right away, make sure that it has the chance to happen soon.
  4. Learn something from each call. Could you change the pitch to be shorter and to the point? Did you feel like you need to connect a little more before asking right away? Always iterate.
  5. Don’t waste anyone’s time. They’re busy trying to make money and you’re trying to get them to spend it. Some people don’t want to make time to chit-chat, but others won’t mind giving you some insight into their business, motivations, and needs. Feel them out and see what information you can get from them, but don’t be pushy. If they’re short with you, move on - there will be someone else that’s willing to converse. If they’re long-winded with little interest, go ahead and cut the conversation short.
  6. Keep your pitch short and try not to make compromises - establish what you’re bringing and don’t sell yourself short.
  7. Be clear on the next steps, even if you’re rejected. If they’re interested, great job - make sure you’re available and can make your promises. If you’re rejected, give them an easy way to get in touch and tell them you’ll follow up with them later to see if their situation changed.
  8. Talk to the decision-maker - but be friendly to the person you speak with - they are your in.
  9. Over-deliver on your promise. You want to make sure they know that they made the right decision.

Why you might consider cold-calling

Why cold call instead of launching a website or creating an email list? Personal connections go a long way. I chose cold-calling because I believed it was going to give me the quickest results. Had I needed to take my salesmanship up a notch, I could have sent them emails regularly to make sure I was top of their mind when they needed someone like me. At the time, that one connection was all I needed.

Additional Resources

Motivated to make that first call? If I didn’t convince you, check out some of these:

The Only Cold-Calling Script You’ll Ever Need by Kent Holland

7 Steps To Cold Call Like a Champion by Stian Pedersen

If those don’t help, maybe you should just start calling people.

in business

Nearly 15 years ago I attempted to buy a used car thinking it would be a quick trip to setup a monthly payment and walk out with an inexpensive car that might last me a couple years. Instead, I ended up walking out with a gentleman’s agreement for website design in exchange for a car that lasted me nearly 10 years.

I had driven by this one particular used car dealership a countless numbers of times over the years and paid no attention to it. When I was looking to get a second car, I kept my eye open for anything on the side of the road, when I spotted an inexpensive aging car in it’s lot and decided to stop in.

Without any planning, or cash in hand, I walked in to see what I might need to put down to walk out of there with it in my possession. It was a small place with 20 cars tops. The guy that owned the place was also the salesman, a really nice guy, probably my dad’s age, running a mom and pop business. He was charming and straight shooting and I was sold on the car pretty quickly - he was clearly good at his job.

Like any good salesperson, he asked about me and what I did for a living. When I told him that I made websites, he was determined to pick my brain about what it would take for him and his business to finally embrace some digital presence and get online after procrastinating for years. I was more than willing to share my knowledge. Then we moved on.

When it came time to discuss the paperwork and down payment, he hesitated as if he didn’t want to sell it to me - he wanted to talk more about how I might be able to help him out on his website. In all honesty, I wasn’t really interested in taking on any more freelance work at the time, my life seemed pretty hectic. When he, very straight forward, asked if I would work on a new site for him, I politely declined. I even offered up a bit of advice - I bet I could help find him a college age student that would work on it without breaking his budget.

This is not the car that I got but it is something I would like to eventually have sitting on my lawn
This is not the car that I got but it is something I would like to eventually have sitting on my lawn

That was exactly what he wanted to hear, I guess. His reply to me declining was “well that’s exactly why I want you to do it”. I guess he liked my honesty and put down the pen on the paperwork to propose that we barter for the car.

I’m pretty sure I audibly chuckled.

I can’t say I’d ever bartered for anything other than brown bag food with my classmates in elementary school. Was he seriously saying I could just make him a website, something I do in my sleep, for the car? I guess it was as mutually beneficial as could be because it took less than five minutes for me to talk through with him what I would expect out of him and what I would deliver. He stopped the paperwork and moved on to the temporary tags and getting me out the door with the car.

I walked out of there with no contract, just a gentleman’s agreement. Over the next 6 weeks I helped his business get online and setup to take online inquiries and list new vehicles. I’m glad to say that it couldn’t have gone more smoothly, something that always worries me about new clients.

Who would have known that car lasted nearly 10 years, but now I happen to need a new car and I know where I’ll be headed.

I can’t wait to see if they need any updates to their site.

in business