Doug Osborne DOES NOT QUIT

I’m a very talented and experienced software engineer who once had a successful career (see: Background), but I became depressed after leaving my startup company and moving to Chicago at the end of 2013.  As a result of this depression, I haven’t been employed since 2016 and I’ve been on Social Security Disability Insurance since 2018.  

Since going on disability, I’ve pursued my own unique software projects with the idea that eventually one of them would lead to my success again.  While I’m proud of these projects shown on my portfolio, 2020 was a low point for me because they hadn’t led to anything yet and I was running out of ideas and motivation to write software on my own.

So in 2021, I went on a mission to get a position at a company where I can make a difference solving problems again.  While I’ve worked very hard towards this goal ever since, it’s taken a lot longer than I thought it would.  The day after I submitted my first job applications in over 7 years, my landlord told me that I had to either buy his house or vacate his property in less than one month.  While I nearly got the best paying job of my life from my very first application, instead I had to postpone my job search to find another place to live. 

Since then, I’ve accomplished a lot along my path towards applying for jobs again.  I successfully defended myself in an eviction lawsuit, and I bought my first house, a four-season vacation home in Summit, NY.  I fulfilled a commitment I made to a friend by writing the Puzzle Box software featured on this website.  I used this software to make my mother a 120-piece painted Christmas Tree Box and my brother a 108-piece wood-stained Sphere Box.  I’ve gotten back into shape and have run over 500 miles and lost 30 pounds since moving here.

I resumed applying for jobs earlier this year, but I took a break to make my brother’s sphere box after only about 10 applications and one interview.  Afterwards, I was feeling a bit down because for all that I had accomplished since 2021, I still hadn’t completed my mission.  So I started thinking about the best year of my life and the Doug Osborne that I’ve worked very hard to become again.

2012 was the peak of my life.  That year, I was at my best professionally working from my home in Woodbury, CT.  This was the year that Minify, LLC was conceived, a company started in 2013 to market and sell the eDiscovery software that I wrote for Digital Legal Services.  This was also the year that I did 4 triathlons, 4 road races, and a 103-mile charity bike ride.  

My first race that year was just over ten years ago, when I won this medal on a 90-degree day in May when a lot of other people were quitting:

Thinking about this race and others that year, I remembered how I was able to push myself harder than anyone else, all the way to the finish line.  Any time I thought about quitting, I told myself that “Doug Osborne DOES NOT QUIT.”

This phrase has become the title of my personal redemption story because in December 2020, I was a shell of my former self and nearly quit trying to do anything about it.  It’s also the only rule that I have to and will continue to follow to keep myself hitting the apply button so I can finally finish this journey that I started over a year ago.

In case I ever have doubts and think about quitting, the following banner will remain outside my house for the world to see until I cross the finish line that I’ve fought long and hard to reach.

I start every morning by looking at my banner and saying “not today.”  But the best part of my day is after I’ve worked hard on my mission and then kick my ass until I finish my workout, and then I get to say it like “NOT TODAY!!!” because I DID NOT QUIT today.  Now I even have a NOT TODAY! sign out by my mailbox: 

It will be the best feeling ever when I finally complete my mission and I get to hang an even bigger banner with the same words and my next company logo on it. Then I get to start a new mission, because I’ve promised myself that I WILL NOT QUIT until I’ve made an impact wherever I end up working next.  

I plan to yell “NOT TODAY!” 365 times in 2023, because I don’t plan to quit fighting any of them days.  Watch my first “NOT TODAY!!!” of 2023: NOTTODAY_NewYears2023

My New Year’s resolution is to keep fighting no matter how many times I get knocked down and feel like quitting.  In 2022, I was knocked down a whole lot while pursuing last year’s resolution of getting a remote software engineering position and going off of disability.  

Since I hung my banner last May, I’ve been rejected so many times that it feels like I’ve been playing 1-on-1 with LeBron James.  I suspect I was being turned down because I haven’t been employed since 2016 and/or I am on disability, because I can count on one hand how many times I was rejected before I began my mission.

With everything else I’ve accomplished since 2021, I earned the respect of many nice people who now support me on my mission, while I can tell that others won’t believe in me until I finally succeed.  Unfortunately, people in the latter category can make it so much harder for a poor guy on disability fighting for a second chance at life.

Conversely, I am extremely grateful for everyone who has supported me, many of whom can’t believe that no one has hired me yet. This includes many of my new neighbors around Bear Gulch Lake in Summit, NY.

Over the holidays, I took a break from applying for jobs to make gifts for as many of my supporters as I could.

I have even inspired a few of my supporters who have told me they are glad to have met me.  Of all of my recent accomplishments, this is the achievement that I am most proud of, because my personal redemption story is not just about becoming successful again, it is about becoming a better person.

I look forward to proving everyone who has doubted me wrong by proving my supporters and whoever finally gives me that second chance right.

For my 42nd birthday, I’m sharing a video because Coach Prime gave me the gift of a title for my third book, Do You Believe Now?

My first book, Doug Osborne Does Not Quit, covers the start of my mission of getting a job and going off disability. The sequel, Not Today!, will conclude with its successful completion. That should have happened long ago, but I am still fighting. In 2021, I nearly ended it with my first job application since 2013. In 2022, I applied for hundreds of jobs and interviewed with dozens of companies. 

The memories of last year’s interviews are still fresh in my mind. A lot of companies passed on a great opportunity to get a very talented and determined software engineer and problem solver. Many recognized the talent but lacked the vision or courage to hire me, likely because I’m “different” and I’m on disability. Although most people say they believe in giving people second chances, few are willing to put their money where their mouth is.

This year, I took a longer-than-expected diversion to explore other ways to complete my mission, which included writing and promoting my book along with my art.

While it was time well-spent, I’ve been working hard lately to prepare to bomb that apply button again. I am excited to share my new resume and my redesigned website. However, I still expect to fail many more times before I succeed. When I finally do cross the finish line, it will be the end of a long and hard-fought battle, but just the beginning of a war that could last for decades.

Do You Believe Now? will chronicle the fight for my future success. I will begin the road to success by doing whatever it takes to make an impact for my next company. Although my banner is enough motivation, I will be thankful to everyone who rejected me for giving me more reasons to keep fighting throughout my second career.

Because like Deion Sanders, I have complete faith in my abilities and “I keep receipts.” It might be 10+ years from now, but I look forward to sharing my receipts. I expect to send out many free copies of Do You Believe Now? both to those who believed, and to those who did not believe. For now, it is time to finally reach the real-life ending of Not Today!

Who else believes?