Why am I unemployed

Jan 17, 2018 | 6 minutes read

In the middle of November 2017, I did something I never thought I would. Something that just a few years ago I never would have done. Something that surely caused some consternation among my friends and family. The thing I did was quit my job without having another one lined up. This was monumentally frightening to me, I am the person with a years worth of finances saved up, who has a strong retirement plan, no long term debt aside from a house and no credit card debt. In short I avoid risk and prepare for the worst. Yet, it felt right and though I have had moments of doubt I still think it is the right decision. Let’s take a look at some of the setup; but before that I want to start adding why am I blogging this .

Why am I blogging this?

Because I want a history for myself to put it simply. It is like going through my personal journal a few years later, except everyone can read this =). Also I want to chart my journey, and to give some urgency to decisions. I to often find myself complacent and easy to fall into time wasting without a goal or purpose. Warning this is going to an incredibly self centered post.

Work History

Let’s start with the original job that mattered. Homecare Homebase. I was at HCHB for around 11 years, that is a long time in the software industry. I enjoyed 80% of my time there, I love the people and the work can be incredibly satisfying. I learned faster and harder than I ever have in those early days there. From associate developer to senior and then to manager. I managed the Mobile team at HCHB for around 5 years and I can say some of those years are the best work I have ever done. Hopefully my guys and gals also agree =). That being said being a leader who cares and cultivates a team is hard, it’s easy to not care and to see people as just FTE (Full Time Employees) that you move around to accomplish goals. And sometimes you have to, but it’s easy to fall into the trap of not caring.

Then came a work change called Agile that changed the structure and I found myself no longer a leader but a manager who primarily handled HR and projects. This was not a welcome change and I pivoted into a more development oriented role has an architect on the team. This was also rewarding but after being at a place for 11 years I started to realize that I wasn’t growing in the same way I was before. I had become complacent and wanted to see different ways of doing software development, work on different skills. I needed a change. So I started looking, I had great conversations with my leadership and they understood me. So I started looking.

I found a role at Cafepress as manager of a small internal services team. It was also great, very small team ( 4-5 people) working close at hand. Though there was still a tick at the back of my head saying “You are not growing and you are not learning”, then I was offered a role as Manager of Retail, essentially the website. This was with a larger team in a platform I did not have much experience with, this would give me great opportunities for growth. Unfortunately this turned out to be a poor fit for me.

Poor Fit

After a few weeks, I found myself not wanting to go to work. This was especially odd since Cafepress has an extremely laid back culture and many great developer perks. After thinking about it for a long while I came to the conclusion that I wasn’t growing again. The problem I had at HCHB was that I thought after being at a company so long I had exhausted growth (and this could still be true) but I had also done a lateral move into management. In a future post I will talk about the challenged of moving into a hot seat role with a group of people you don’t know that well! I knew I needed to move in one of two directions; higher up the management ladder or closer to development. I needed not just a change in scenery but a change in role.

Road to Unemployment

The leadership team and HR team at Cafepress were incredibly good in talking and working at it from various angles. We had several conversations about options and how to handle the situation. Great thanks to them for accommodating me. Beginning of November I decided to put in my notice. I was going to Germany in early December and with all the holidays it would be a good time to take a few months off. Months, take a second to look at that. I have never had more than a week between jobs since 2005. I knew I had several things to help me do this. Enough reserve cash to handle it, and most importantly an incredibly understanding girlfriend!



At first it was relaxation, Germany, the holidays, a few weeks of lounging and reading. Now that I am reaching out and looking for jobs, having lunches with old friends, reaching out to the network of past employees and companies, I find the freedom is intoxicating. I know what I don’t want, the same old manager role, stuffy development at a huge corporation that talks about people in only FTEs. That leaves a whole realm of options; start my own business, find a small startup, contracting, consulting. I have always been driven by the ability to make change, and now I have the focus and impetus to change not only my environment, but myself. There is fear behind this choice, being afraid of the changes, of holding onto what is safe, what is stable and what is normal. I embrace that, without that then this would not be growth. I wish I could say I embrace it fully, but I do with gritted teeth. I am already having to make changes to myself to accommodate this freedom. Depending on the role I may not make as much money as I once did, there will be less job stability, if I go into business myself there may be no stability! Ask me in 6 months and maybe I will regret everything I have written above, or it could be the best thing I ever did. But that comes with the freedom of choice.