I Built My Dream, and Then Lost It

My clothes clung to my body with sweat as I stood in front of room full of stone-faced software developers. Just moments ago I was struggling to park after getting lost. My iPhone couldn't help me navigate through this foreign country with it's narrow streets and winding roads. Arriving almost an half-hour late, I was lead through the hallways of what seemed like a design studio. American movie posters lined the walls that I walked through attempting to find my composure.

Just remember to breath and speak slowly, I thought to myself as I nervously introduced myself and asked the room to go around and tell me their names. There was no way I would remember any of what they said but I needed another moment to collect myself.

This engagement was unexpected and I welcomed the work after a very slow year in my business. My task today was to teach these software engineers to create iPhone apps for their design company. This was a rare skill in 2013.

Five years ago before, I went down a path that turned into an exciting opportunity and ultimately my own business. This business was more than a job but an unexpected path into a place where I could choose my own way and work on my own projects. Projects that I owned 100%. These projects created a passive income for me that was reliable regardless of whether I worked or not that month.

I had effectively stumbled into an online business building iPhone apps which had allowed way more freedom that I ever imagined. This gave me space that that I used to fulfill dreams that I had since I was a kid. I published books, was asked to teach classes, got to travel, and talked to interesting people.

Today was one of the days I got to travel. The night before my ill-fated start to my class I was traveling from Philadelphia to Antwerp in Belgium. I arrived early in the morning the day before after haggling with a desk clerk to get a car with an automatic transmission.

Halfway to my destination I was caught up in a DUI sting even though it was early on a Sunday morning. As a pulled up a cop barked something to me in Dutch. Sensing my confusion he just said "You English?" before sticking a breathalyser into my open mouth. He waved me along after quickly glancing down at the results.

Random early morning DUI stops not withstanding, my impression of Belgium was that it seemed drab. It was kind of like New Jersey in winter but with odd looking buildings. Even the people who spoke English had a New Jersey accent. It was odd but not completely foreign.

Navigating the streets in Antwerp was challenging and when I finally found a place to park it took me 20 minutes to pay the attendant, an old man who spoke only Dutch. After a few minutes of awkward signing I finally freed myself and ran to my appointment and to a room of engineers who were expecting a show.

So there I was in my sweat soaked clothes feeling flustered. The engineers finished reciting their names and we got our smalltalk out of the way. I just focused on projecting confidence and moving the class along one moment at a time. But I was pretending. My mind had not caught up to my situation in the room and I hoped to lean on my curriculum until lunch at least.

Finally, I finished the first module and we got to the first hands-on exercise and their cold eyes were drawn to their laptops. This kept me out of the spotlight for a few moments. Relief. But, then after only 10 minutes they eyes came back up to meet mine. One by one, these engineers finished their first task in only a third of the time it normally takes people.

By the time we got to lunch, we had gone through most of the material that we had for the entire day. Panic started to set in but I pushed it down and moved onto the second day's material. I tried to slow the pace of the class down but the class resisted. It was almost as if they were just trying to get through the material so they could make the class into something different entirely.

The rest of the week went about as bad as that first day. The engineers in the training had clearly studied up beforehand on iPhone software development. They quickly became bored over my introductory material and asked me to skip the basic parts of the presentation. Each subject that I covered was either something they already knew about or was not advanced enough to deserve their attention.

So the week went on with the developers trying to pick my brain about advanced programming techniques and other content that was far outside our agreed upon curriculum. Some of them would ask for presentations on topics I had no background on and in an attempt to save the gig I would go back to my room and bang out a presentation for the next day.

This clearly didn't work and I was stretched way too thin. By the end of the week we had reached a sort of equilibrium and I managed to get through the class. It didn't fail completely but it felt like a near disaster.

I was devastated. Failure is not something that comes often and I'm just not used to it. The experience really soured me and left me doubting myself. Even though I understood the clients and me had far different expectations and I was not the cause of this class being off I still put it all on myself.

I left Belgium with a few stories and enough money to keep my business running for a few more months. When I got back home in Philly my self-confidence just sort of slipped away. The feedback from the training was mixed, it was not a total disaster but there were a lot of negative comments. The consensus seemed to be that the Belgians thought that I was a nice guy but a hack who "acted like he never did a unit test."

To be fair, they were right. I never actually did a unit test and only learned what they meant by that after getting their survey results back. Unlike the engineers, I was not a trained software developer. In fact, my entire business was predicated on this idea that you could turn a hobby like hacking your iPhone into a new career or even your own business. My audience were not necessarily engineers.

What I didn't realize after setting down in Philadelphia was that along with the money and stories I had brought back a poison pill hidden deep within me.

Motivation started to ebb away and new projects didn't seem to be worth investing much time into. Ideas wouldn't come to me. Royalties and sales from apps were on the decline. The big ticket workshops I was doing were being surpassed by newer and sometimes better products.

In spite of my performance in Belgium, I was offered another training workbook to teach. This would have required me to travel to a remote location in India. It would have been a 20 hour flight and another group of engineers had requests that went far beyond the curriculum I developed. Just two years ago I would have jumped at a chance to take an adventure like that. But I was deep in my own head.

I blinked.

I went back and forth with the booking company and ultimately turned down the offer. I just wasn't in a head-space where I could take another failure. This damaged my relationship with that booking company and I only got one more job from them which they passed along begrudgingly because the client asked me for specifically.

My business has slipping away...

Each month after that my income continued to decline and my new projects felt uninspired. I had to take more cash out of my buffer account just to pay myself and eventually I had to cut my own salary to a third of what I was taking a year ago. Any help from virtual assistants or business services had to be cut. I moved my websites to cheaper hosting and I was burnt out.

The burnout was the most problematic issue I faced. The engine that ultimately fueled by business was this constant string of thoughtful blog posts about iPhone development. After five years of publishing at three three posts a week (all of which had to be researched and tested), maintaining eight iPhone apps, constant Twitter posting, and traveling to supplement my residual income my heart was no longer in it.

There were days that I couldn't even look at a laptop screen. My blog posts became less frequent and I started posting only once a week and even those posts were unoriginal. I had no gas in the tank and I was still broken down by my experience in Europe.

Eventually traffic to my website started to decrease along with the new email subscriptions which were the lifeblood of my business. Then changes to the Google Search algorithm damaged my site plunging my traffic to new lows. I had lost sight of why I was even putting myself through this. Sometimes I would take long walks and fantasize about just working a normal job.

While this was happening my wife and I started to talk about buying a larger house for our growing family. The income from my business no longer was enough and each month it was less than the month before. It was time to make a decision.

So, I gave up on it. Soon after, I started to desperately look for a job. At the time, it just seemed like a smart move that we needed to help reach our goals.

After a few months I found myself in a new job and a new house. Life became hectic for a while.

Eventually, I started to sour on my job. Then I started to sour on our new house. The house was huge and felt overwhelming. There were some weekends where I would spend an entire day just doing yard walk. Even buying furniture and decorating seemed too much to deal with.

Once I passed my year point in my job I started to become angry and negative. The position as it was described to me never materialized and I was sidelined. I started to regret my decision to end my business. I didn't realize it at the time but I had become depressed.

One day I was sitting in my car, waiting to go into the office and desperately typing into my iPhone trying to brainstorm new business ideas. Tears were swelling up as I went through the uninspired list that I had produced. There were other days were I tried to start working on apps again but the software had moved so far along that I didn't even remember how to use the tools.

Things went on like this for years: I would get frustrated and angry at work, desperately flail around pretending to restart my business, and I started to resent my new life. Things at home had become strained. I just never let it go. Even to this day I still think about that period in my life and there is always this thought in the back on my mind,

What can I do to get back onto the entrepreneurial path?

This funk lasted for years and until I found a hobby so captivating that I managed to pull myself away. At the same time things at work finally started to come together. However, my career at that job was doomed from the start. It was just a series of false starts and I was never as invested in the role as I could have been.

About a year or so after my life seemed to start to turn around I had suddenly lost my job. I was devastated, angry, and frustrated again because by that time I had become close to the people I worked with and had some promising new projects. It started with the CIO of the company targeting and then disbanding my team. We found ourselves scattered across the company in roles that didn't fit us.

I didn't know how to manage my new role and I was also not motivated to put in extra effort to start over doing something I didn't really care about. My manager would give me feedback like "I just wish you were more curious (about the tickets the had to work on?)" One day I asked for help and that conversation started a process that would end in my termination six weeks later.

Even though I basically despised that company and that role by that point I was devastated. I just seemed that I was racking up more and more losses. First the business and now I can't even keep a simple 9-5 job.

I shut down for a while other than doing family things. Again and again I attempted to restart an online business but I was uninspired still. No ideas and I didn't follow through with anything. Some weeks I would take online courses to get certifications. Eventually, my unemployment ran out and I started to take odd jobs. I didn't really know what to do and felt like a failure. It seemed like I was too old for a new tech job. There was a point where I felt like my professional career was over.

I was still angry about losing my business and being in this position. And I was embarrassed about getting fired from my last job, even though I realized that it was not really my fault. This was about five years after that job in Belgium. Six months after that termination, I started to drive for Lyft.

This was mainly a way to avoid taking on a new job. I just wanted more time to try something different. The last job just seemed like the wrong choice, even before I was having trouble.

The pattern I got into with getting angry about work and reminiscing about my business remained. By this time I was completely obsessed with my hobby, FPV racing drones, and so a lot of my energy was going there. But even that hobby was influenced by my business. Part of the allure was that FPV racing was something I thought I could have turned into an online business. Ultimately, I was wrong about that but that hobby was the closest I had became to getting inspired enough to try again.

Eventually, I became frustrated enough with Lyft driving that I found another job at a local college. This job turned out to be a complete disaster and I started to miss even the position I had the year before that I thought I hated. I started this job two months before the Covid pandemic started in 2020.

This new job started off bad in the first week with my new manager coming into my office and crying because of how terrible the other staff were treating our team. Office conditions were completely unacceptable. It was just an overall bad situation and not at all what I expected from working at a local college.

My mood got much worse in those first three months. Things were so bad that my wife begged me to quit a few times. If it wasn't for the covid pandemic I would have left that job as soon as I had the chance. Things eventually settled down there.

The pattern continues. I've been at this "new" job for around four years now. The roles have been changing so often that I can't even really tell you what I worked on and what I have accomplished. My list of crazy work stories from this place grows by the day. I still think and talk about online business and I still don't feel like I belong in my role.

My business officially ended ten years ago but it may as well ended yesterday.

I still get angry at work and sometimes it's not obvious why. Even though I've some of my best work in the past ten years I don't seem to be able to get any traction. My heart is still in that business that has been gone for ten years.

And this is what it's like to find your dream and then lose it: one day you get what you always wanted but there are no guarantees that it will be here tomorrow. Things fade. Raising to great heights makes falling to new lows even more painful.