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As I write this, I am watching the hour glass run out the last few hours of my first five decades breathing life on this earth. By the time I am done, I will have started my sixth decade. To borrow from Bill Clinton's speech before the DNC, I have more yesterdays behind me than tomorrows ahead, but there are moments such as these, Dr. Who would call them Fixed Points in Time, where you cannot help but take a moment and reflect.

Where I am now is not where I thought I would be when I was a child, though I expect becoming an astronaut was always a shooting-for-the-moon kind of dream. I'm not where I thought I would be when when I was 25, young and full of ambition and energy. This is not the life I expected for myself even a short decade ago when I turned 40. I would bet I'm not alone in these thoughts, and I am envious of those who had the ability to set out life goals at a young age and then check them off the list, one by one.

Frankly, 16 years ago, I wasn't even sure I would reach age 50. I had just been diagnosed as a Type II diabetic and felt life as I knew it was over. I have learned over time that different is not the same as "over". I began eating better, taking medication, even returned to exercising, something I had never been very good at sticking with. I still work out three times a week with a trainer and stick mostly to a controlled carb diet.

And yet, Diabetes is uncurable, degenerative disease. When first diagnosed, my Dr. said my #1 job was to stay off insulin for as long as possible. In that sense, I have been successful, though it has been a rollercoaser struggle. Right now my A1C number is lower than the worst case scenario but not as low as I would like it to be, or it used to be. Such is the ongoing battle against a disease that does not play fair or follow consistent rules.

I bought my home at age 29, and refinanced back in 2004, so I am on target for paying off that mortgage in less than 3 years. Of course, I still have a large HELOC balance from a major renovation I had done 8 years ago. There's still more work I would like done to the house, but I don't have the resources right now. The first renovation took over a decade to be realized. I still have a couple years left before I match that mark.

As for retirement, I wanted to have achieved half a million dollars in invested savings by my mid-century mark. Thanks to the market tribulations, I have fallen short of that by about a small amount, and while I've watched some investments go down in flames, I've seen more reach for the sky. I am a die hard buy-and-hold investor and I think my biggest challenge is going to be to start reigning my aggressive risk tolerance and begin introducing a little more conservativeness into my portfolio.

The second half of my original goal was to grow that half million into a million or more by retirement age in, say, 20 more years. That's still pretty aggressive - I took almost 30 years to reach this point, and am giving myself 20 years more to double it. The last 30 years have been complicated by the fact that I have not worked consistently over the years, and many years have been lean, without fresh contributions into my retirement savings.

As I expect this aspect about my financial life to not change in the near future, it will make achiving my retirement goals more challenging. I will be depending significantly on growing my portfolio though investment growth, so there is a lot riding on making the Foolish tenants of invetsing work for me. I again imagine that I am not alone in that hope. I have positions in 136 companies to date, and a cash infusion coming up from rolling over my old 401k. I am looking forward to being able to make fresh investments as I continue towards my goal.

And speaking of hope, I am basically an optimist. It doesn't always show, I don't think, but then again, maybe it does. Being an optimist can be difficult road to travel when life is constantly throwing you enough road bumps and obstacles to make even Job's trials seem trivial. I think this is one of the reasons I appreciate the life of Walt Disney so much. Can you believe I'm 9 paragraphs into this treatise and I've only just mentioned Walt Disney? Walt faced failure, bankruptcy, theft of Intellectual Property, and a steady flow of naysayers as he followed his dream and vision. I would be lucky to be even half the man he was, and I know I don't even measure up to that.

When I was in high school, I didn't know what I was going to do professinally but imagined it would be in computers. I started out college planning to be a CS/EE but soon realized that logic circuits made no sense and went straight Computer Science. Once out of college, I got my first job a few months later as a programmer, worked for a year and then was fired just weeks before I would have earned benefits. I learned the lesson that employers don't always play fair.

I went through a couple more jobs, one where I became fustrated that the product was not developing fast enough for me to become useful, and I left for another job in support where I thought I could help people. But it soon became clear that I had different ideas of what help meant, and when I refused to advise clients to take actions that I knew could damage their computers, I was accused of "maliciously not living up to my potential".

To this day I don't know exactly what that means, but it sounded really damning to a young me. I learned to not work for praise but for a paycheck. After a 10 month period of unemployment, I struck oil, turning a fresh networking certification into an 11 year career at Turner Broadcasting System, working with the Turner Entertainment Networks (TBS, TNT, Cartoon Network, TCM, etc.). This lasted through the Time Warner merger and into the AOL merger. In 2003, like many coworkers, I finally fell victim to the worst merger in the history of buinsess mergers.

While at Turner, I had developed a diverse collection of IT skills and experience but rather than compete with the next generation of young, eager technologists, I decided instead to focus on the niche area of database reporting that would later be given the buzz word of Business Intelligence - the art of retrieving raw data from company information systems and packaging and presenting it in ways that a business would find useful. This was something I was good at, something that would draw upon my diverse IT background, and something that would set me apart from everyone else and hopefully earn me a premium pay rate.

And for the most part, it did. I embarked on a contract consulting career, working short jobs, long jobs, and sometimes, no jobs. It was not a period of job security, but it did offer a degree of independence and an opportunity to be exposed to a wide variety of businesses, work environments and technology implementations. In 2006, I turned a 9 month contract into a full time job at Avaya that lasted for 2 more years until the company was taken private. After reassuring employees that we were their most valuable resource, the new owners began a force reduction and I was back to knocking on doors again.

Not for long, as it turned out. My prior contract work and my growing list of hard and soft skills led me to a series of jobs, including a Disaster Recovery, Continuity and Business Resilliency project for the IRS. Against all odds, I received a security clearance to Secure but Not Classifed information. It turns out, the same company who processed my application also granted Eric Snowden his, so I'm not sure what that says about mine. This job lasted nearly 2 years until Congress allowed the Sequester to take effect, and funding for the project was slashed, along with my position.

It was purely by chance that I landed my last job with Tyler Technologies. I had applied online without paying much attention to who or for what I was applying largely to satisfy the Department of Labor's requirements that I demonstrate I was looking for work. So when I got called by HR to schedule an interview with the hiring manager, I was taken by surprise. I asked for a premium salary and was again surprised when they agreed to it. You can check over in the Ask The Headhunter board, it's not supposed to work that way.

My time at Tyler lasted just a week shy of 3 years when we parted ways. It was not by my choice, but I knew the writing was on the wall. The company was growing quickly and experiencing growing pains that impacted benefits, client relations and more importantl to upper management, margins. Our values had begun to diverge and I think a fresh start will be healthier for me. What else am I supposed to think, I'm an optimist.

So nine career paragraphs later, here I am at 50, out of work and hoping I have enough savings and credit to carry me until my next job, be it contract or direct hire. I have a few leads which I won't jeopardize by discussing. But my financial obligations are bigger than they were last time I was on my own, healthcare costs are significantly higher, and I know that despite being illegal, age discrimination is a fact of life. My only consolation is that I am pretty confident wherever I end up, I'll at least be making about 30% more than a woman my age with the same skill set.

Of course, she might be more likely to get the job for the same reason.

This is not where I once thought I would be at age 50. I thought I would be a 30 year career employee somewhere, having risen up to the top, gone into management, been a CEO of my own company. I've come to realize that despite all the glorified profiles of successful executives, that's a rare path for one to follow, like reaching the Major Leagues in baseball, turning an audition for a televised talent show into a successful entertainment career, or going from being elected to the School Board to being elected President of the United States.

I thought I would be at the top of my game, the venerated senior employee to whom others looked up to for advise. Instead, I am resetting once again to the role of last-one-in, working for only 2 weeks vacation and paying my dues. When I get a new job, that is. Or not getting any paid time off at all if I go back to contract work, not knowing for sure when my next job will come or how long at last. It may seem romantic and exciting to be professionally ree, independent, not tied down. But after a few decades of that life, I increasingly look forward to the security and (relative) safety of long term work.

But still, even a decade ago, I thought I would be gainfully employed, secure in my financial future, and married with children in college, or even out of college, married themselves with grandkids. None of that is my life today. I have more questions than answers, despite my frequency of replies on the boards would lead you to believe. I am looking back on a life of lessons learned, yet looking forward, I see too many unknowns and uncertainties for comfort.

Don't get me wrong, I think I've built a solid foundation. I have some accessible savings, through most of my assets are tied up in tax-advantaged retirement accounts. I have excellent credit - my score is over 800 - but without income, I cannot refinance my HELOC to tap the $100k in extra equity (according to Zillow). I have a number of financial obligations I need to honor, but I have money set aside for most of them. And don't even get me started trying to navigate the murky waters of COBRA, the Healthcare Exchange and private insurance options. Plus AARP started sending me applications a week ago.

With the help of Senior Citizen discounts, I should be able to get by for two, three months before I start digging myself into a debt-filled hole. I'm counting on not being unemployed any longer than that, but cutting back my spending in case I am. All the while trying to keep my diabetes in check, my mind active and my body in motion. The state of Fuskie is on a razor's edge, but I've walked this knife before and am confident I can do it again. There's that pesky optimism again.

But as I look back at the last 50 years, I can't help but think to myself, dude, you're getting too old for this.

Who is in his 17th year with The Motley Fool and wants to thank each of the Fools he has met in person and on the boards for their advice, their trust and most importantly, their friendship...

Ticker Guide for The Walt Disney Company (DIS), Orbital ATK (OA), Intuit (INTU), Time Warner (TWX), Titan International (TWI)
Disclaimer: This post is non-professional and should not be construed as direct, individual or accurate advice
Disclosure: May own shares of some, many or all of the companies mentioned in this post (
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