So This Is What Failure Feels Like:

My boss had called me into his office.  I was responsible for selling software no one seemed to want.  On his desk was a piece of paper listing all the issues he had with my performance. Some of them were true, some of them weren’t. Some of them made me feel absolutely horrible.  He wanted me to sign it or resign, but I didn’t think that would help me.   So I begged to stay on and try to make it work.  I didn’t sleep that night, and I barely slept over the next two weeks. It was my responsibility to provide for my family, and I’d failed. I was terrified of having to move back in with my dad and start my job search all over again with the thought of having been fired weighing on me, and everyone knowing I was a failure.



I had taken this job after desperately searching for nearly 6 months. I had gone on countless interviews during that time, many for jobs I didn’t even want or that didn’t pay anything we could live on. Our plan was for me to find a job in Central NJ so we could move there, and I would support my wife while she went back to college to  become a teacher.  But I didn’t have any contacts in Central NJ in the technology industry,  even though it was about 40 miles from where I had grown up and worked for the past 10 years.  Even people who said “call me if you ever need a job!” hadn’t been able to help me.

The job I had taken was for a software company,  selling software and services.  I was excited when I first came across the opportunity. I had previously used extensively and loved it. I had even worked with my former employer’s Salesforce Administrator making some pretty cool queries to monitor the work my colleagues were doing that I was responsible for.  I was happy to share that experience with this potential employer.

On my second interview with the company, I asked to see the software I would be selling.  It was, undoubtedly,  an extremely unattractive user interface.  Looking at it, I was transported back to the days of Windows 3.1 (that’s pre-Windows 95 for those of you who weren’t around back then). That should have been the warning sign that made me pause. But I was so desperate for a job, and this one seemed to be a great way to make money, because each sale was BIG MONEY.  I took the job.


From the first time that I used the software I knew I couldn’t get passionate about it. I tried, but not very enthusiastically. I just couldn’t bring myself to get excited about this clunky, cloddy software and how much it cost. But I tried.
Looking back on that day when my boss brought me in to review that list, I had known all along that the job wasn’t a great fit. I had never stopped my job search, but I’d also tried to find my niche within the company.  My boss’s mindset was that I wasn’t spending enough time working, that I needed to spend 16 hours per day trying to find opportunities and close sales. Since I had a wife and a life outside of work, I knew I couldn’t do that, even if it was software people truly wanted and I was excited to sell.

I stayed on and re-doubled my efforts, both within the company and at my job search.  I had plenty of sleepless nights. I called anyone and everyone I could think of and explained the situation, looking for help.  I went through my old stacks of business cards, which I realize are no longer useful (why save them? Just use LinkedIn and Twitter).  I had a couple of interviews and opportunities, but they didn’t pan out or didn’t pay an actual salary.  I happened to meet a venture capitalist at an event, and started some really interesting conversations with him that, in retrospect, I wish I had continued.  He expressed a lot of interest in getting me set up on my own, and beautifully addressed my concerns about not having a steady paycheck.

Finally, a company that I had helped previously brought me in for an interview, and I ended up getting a job there, working on their IT needs. I was so grateful to them, I don’t think I could ever find a way to express that gratitude fully without coming off as looking crazy.

The whole experience taught me a lot. Desperation, even if it’s eating you up inside, isn’t a reason to ignore clear warning signs that go directly against your thought processes.  Also, I can’t create passion in myself around something I’m not excited about – either I’m interested in it, or I’m not. Trying to force yourself to like something and then get others to like that so they want to buy it – that will never work.

I also learned that jobs come and go.  It’s ok to cut your losses and walk away sometimes, because the painful, scary moments are what make you grow.  I can truly say that I learned more about myself and dealing with adversity in those few weeks then I did at any other point in my life.

Looking at where I am now, I know that since I survived that, I can survive much worse. I wasn’t a failure because I didn’t give up,  I knew I had value to offer someone – and now I’m on a mission to show that value to everyone I meet.