Staying Sharp For Delaying Your Retirement

Delaying Your Retirement

The biggest risk we have as we approach the later stages of our careers is becoming obsolete. It’s easy to neglect keeping up with the latest advances in our industries or in technology. We risk being left behind and worse, disposable. We need to take responsibility for not allowing ourselves to become victims of ageism. Therefore, it is critical to stay relevant by keeping your skills fresh and up to date if you planning on delaying your retirement.

Just think about how much the world has changed over the last 30 to 40 years. Also, with our longer and healthier lives, the skills we need in order to continue to thrive will evolve. Education is no longer a one shot event. It is a continual process that should never end.

Bill’s Story (Not his real name)

Bill was an estimator. In putting together estimates you need to compare quotes and scopes from competing vendors. This is done by assembling a spreadsheet and comparing line by line of each scope. The problem was, Bill, who was in his 60s, didn’t know or want to learn Excel. He created his spreadsheets by taping together green accounting sheets, big enough to cover a desk, and doing everything by pencil and calculator. The possibility of errors by using this manual method was significantly more than using a computer, never mind how much time it took. And after one particularly big mistake, he was let go and replaced by an estimator who was up to date with current tools, like Excel.

Time To Do Your Homework

Now it’s time to do your homework. No matter how much you think you know, there is always room in your toolbox. Don’t be lazy. Open your eyes and do some investigating:

  • What are the latest industry trends?
  • What new technology is being introduced?
  • Chat with the younger folks? What are they using that you’re not?
  • Don’t ignore industry publications; even the ads can give you information.
  • Assess where your skills are compared to peers.
  • What skills and certifications are you missing?
  • Ask yourself “If I was hiring someone for my job today, what skills would the best candidate have?”
  • Where are you at risk of being left behind?
Delaying Your Retirement


Keeping up with the latest tools and apps can be a challenge for anyone, especially us more seasoned professionals. I’m reminded of a cartoon of a guy leaving a store with his new computer. As soon as he hits the sidewalk a flag pops up out of the box saying “Obsolete” and the same goes for us. Our generation is probably the last one with a built in fear of technology. But we are the ones who need to work hardest to grasp it. Our kids sure don’t.

Invest In Yourself

Delaying Your Retirement

School is not just for kids. There are 20% more people between the ages of 40 and 65 in college today than there were in 2000. Make the investment of not just money but time. Talk to people in the industry who are knowledgeable about the direction you want to go. What are the latest trends? Where do you see things going and what skills will be needed? If you commit to developing new tricks, create a plan and have goals to help you stay on track and get the tools you’ll need to delay your retirement on your terms.

Resources For Learning

Return to school

Community Colleges around the country are leading the charge by working with local employers to develop programs for in-demand jobs. Attending classes is the best way to hone your skills and connect with like-minded people. Many state and community colleges offer tuition waivers for people over 60 and some over 62. The amounts vary from 100% waiver to a fee of $50 and seats may be limited. Check with your local colleges to see what is available.

Online Learning

If time is a challenge and you want to keep your future plans under wraps, online courses through the local colleges are a great options. There are a bundle of online courses available through internet education companies. I’ve personally like Udemy and Skillshare which are apps you can get for your phone or tablet. They offer courses in everything from computer software training and accounting, all the way to learning to play the ukulele. Other highly rated internet course providers are LinkedIn Learning and Coursera. YouTube is another source for educational material from manufacturers, software tips and other skills.

 But my all-time favorite online learning resource is Khan Academy. It was started by a really smart uncle who lived away from his family but wanted to help his nieces and nephews with their school work. He started developing online tutorials that helped them learn basic things like algebra and physics. His tutorials started getting handed around so much he made them available to the public on YouTube. Thanks to contributions from Google, AT&T, and Microsoft it has expanded to now include computer science, finance and a bunch of other topics in different languages. Even today, Khan Academy is free but they accept contributions. http://www.khanacademy.org

Delaying Your Retirement

Audiobooks & Podcasts

How do you spend your time commuting to and from work or other time traveling? Audiobooks, audio programs and podcast are a great way to improve your skills and general knowledge. Whether you want to learn management, finance, history or learn a language, the time you spend behind the wheel can be a great classroom. The best part is that through your local library or a phone app, these are free. For the last few years I’ve been learning about retirement options and starting a blog through a variety of podcasts hosted by the experts in those fields.

Blue Collar Issues

Labor intensive jobs don’t lend themselves to delayed retirements as easily as college educated professionals. This doesn’t mean they are to be excluded, remember Paul the electrician from the previous post. https://yourextrainnings.com/8-steps-to-delay-your-retirement-at-your-current-employer/ With training I’ve seen plumbers become estimators and CAD coordinators. Their field skills add a level of practical knowledge to their new roles that increases their value. People and businesses need to be creative and flexible in order to not lose this mutual benefit.

I Would Love To Hear What You Think

Please leave any questions or comments you may have. In my next post I’ll detail why it’s important to re-establish your network and the ways to go about it. If you provide me with your email, I will send the next post directly to your in box. https://yourextrainnings.com/contact/


Your Extra Innings


It’s never too early or too late to strategize and plan. Take this seriously. In last week’s post How To Delay Your Retirement At Your Current Employer https://yourextrainnings.com/how-to-delay-your-retirement-at-your-current-employer/, I laid out the various work arrangements that are possible. In order for it to happen, you are the one who has to be proactive and come up with a plan that can be sold. Like many things in life, you are responsible for your results. Take planning Your Extra Innings seriously and it will work out your way.



1. If there is an employee handbook, take the time to review it for anything related to retirement, part-time work or anything in these areas. Know what the company policies are.

2. Don’t become obsolete and disposable. Stay on top of changes in the organization and industry. Don’t fall behind with technology. Are there things that other people are using that you are not up to speed on? Talk to the younger people in the organization. What are they using? Is there someone who could help you? Are there classes you can take?

3. Gather intelligence. Look at your situation from your boss’ point of view. What would their needs be? What issues would you need to address? What would they need to hear to buy in?

4. Pay attention to what is going on with your job and how it relates to the business. How does your work benefit the organization the most? What do you do that no one else in the organization does? What parts of your job can be done by others? How can you design a flexible work arrangement based on those questions?

5. Know your numbers. How much do you need to earn? Can you afford a cut in pay in order to be able to stay on their health insurance plan? Are you willing to give up paid personal time? You have to create a plan that is financially workable for your boss.

6. If there is a pension involved, review with HR the impact of reduced hours leading up to retirement. There also may be an issue with Social Security Benefits if you reduce your income leading up to the point you claim. I’m not an expert on either so talk with a financial advisor.

7. Create a written proposal that includes:  Your work schedule.  An outline on how your current duties will be handled by you and by others.  Work arrangement options including pros & cons of each: • Part-time • Freelance • Consultant • Phased retirement  Pay and benefits options

Your Extra Innings

8. Negotiations: Create a vision for your employer of how it will be when you are successfully working under the new arrangement. Focus on the benefits to your employer, not you. 

9. Don’t expect or push for an immediate response to your proposal. Your employer will need to digest this and probably talk with HR before any decision is made.

Paul The Electrician

This is a story about a guy I worked with named Paul. Paul is a commercial electrician who was 62 and near the end of his career. Being an electrician, some days Paul had to climb ladders installing heavy lights or climb into a trench and wrestle with 4” pipe. He knew that time was quickly coming to an end.

But Paul didn’t want to retire. He enjoyed working with his friends, and he liked going to the jobsites. So Paul took a look at the work he was doing and realized that besides installing the electrical work, his employer relied on him to do the layout work ahead of the crews. This way, when the crews got to the area Paul did the layout, they could just install conduit and not wait for someone to figure out where it went. The thing was, doing lay out only took Paul two days a week to stay in front of the crews.

Your Extra Innings

So after considering his options and creating a plan that he felt was good for him and his boss, he approached his Boss. He laid out his situation that it was either he was going to retire soon or he could just work two days a week doing nothing but layout. His employer didn’t want to lose Bob’s skill and knew this was a way of keeping him around for a while longer, so it was an easy decision. Bob even coached a couple young electricians on layout and measurement while he was working, ensuring his skill would continue on after he eventually retired. Everybody was a winner.

By taking the time and effort to review your work situation and being proactive, you can come up with a plan that helps you delay your retirement on your terms. But you have to take this seriously and make it happen. You can’t hope things will work out well.

If you believe it will work out, you’ll see opportunities. If you believe it won’t, you’ll see obstacles.

Wayne Dyer

Your question and comments would be appreciated. In my next post I’ll get into why it’s important to maintain life-long learning and the ways to go about it. If you provide me with your email, I will send the next post directly to your in box. https://yourextrainnings.com/contact/


I created this blog to share what I’ve learned over the last few years as I approached the end of my career. I stepped away from normal employment and reinvented work on my terms.

My Story

My career in the construction industry included roles as estimator, project manager, operations manager and president of a couple turnaround adventures. During this time I also served on the boards of industry groups and non-profit organizations. After years of traveling to assignments in Washington DC, Boston, Albany, and many other stops in between I decided it was time to reflect on how I wanted to spend the later stage of my career.

As I went through my career, I drifted further away from what I really liked doing. I climbed the ladder gaining power, influence and money, but in roles that I wasn’t truly happy in. Looking back, I realized what made me really happy was working on projects, getting mud on my boots and working with the trades helping to build buildings. With the help of friends in the industry I am now a freelance project manager working on a project by project basis. Over the last 5 years I’ve averaged 7 months of full or part-time work a year. The best part, I was doing what I loved.

Our Story

Somewhere between 18 and 22, most people pick a career path they are supposed to travel along for the next 40 plus years. Maybe it’s the right path, or maybe it’s not. But after car loans, marriage, a house, and kids, there is seldom any opportunity to make a change. People feel trapped and endure a career that provides a pay check but not the satisfaction they felt early on. There is a desire to make a change, to rekindle the fire they felt before. They may know what they want but don’t see a path to get there.

Why Your Extra Innings? Look at your life as if it’s a baseball game.


Your First Three Innings

In the first three innings, you are born, learn to walk and talk and hopefully graduate from diapers. Next comes school, sports, dance and so on. Through this stage you grow and develop towards adulthood. This includes education for the development of a trade, an employable skill or college. The 3rd inning ends with walking through the door into adult life and work.

Innings Four, Five and Six

Inning four starts with you getting your first new full-time paycheck which leads you to your first new car and its payments, your first place away from the nest and its payments, your first serious love and its payments, and then probably kids and their payments. You are beginning the process of buying a house, then a bigger one and then nicer cars, and all the “keeping up with the Jones” stuff. Inning six ends with you being a full fledged member of the Rat Race.

Innings Seven, Eight and Nine

During the final three innings life starts to change. Around the seventh inning the kids will be going through their own first three innings and will soon be moving out of the house. You and your spouses career’s have taken the routine steps up with more responsibility,  pressure and hopefully income.  In the eighth inning your still have the mortgage, car loans and college loans but you are starting to think about your later years. You probably will go through your mid-life crisis or menopause, which gets you thinking about what you are going to do now? You enter the ninth inning with the glimmering light in the distance called your retirement years. You’ve heard tales about this mystical world. As you get closer and it starts to come into focus you start to wonder “Is it real?” “Do I want it to be real?” “Will I really be able to enter it?”

Your Extra Innings

The game is almost over and you and your life are all tied up. You thought about that new recliner, remote control, fishing rod and that book club you wanted to join. But you are realizing that you may not be ready for that. The prospect of delaying your retirement is a real possibility. You may have to work to live the life you want. You may want to work to continue the life you enjoy. It’s the bottom of the ninth inning and it’s time to plan Your Extra Innings.

Where Do I Come In?

This is where I can help. Through my first-hand experience in successfully making the shift to an alternative retirement, interviewing others on this path and studying the experts in the field, I can provide insights and tools on how you can take control of Your Extra Innings. 

Some of the topics I’ll be covering are: Reasons you may want to delay your retirement, Reasons you may have to delay your retirement, How to delay your retirement at your current employer, Staying sharp and up to date, Networking, Proper care and maintenance of you as we age, Un-retirement, Ageism, and Being Proactive and in control of Your Extra Innings.

I look forward to being a guide, mentor, and coach to help people navigate this potentially stressful  part of their lives.

Become a subscriber to the blog and you will receive my weekly articles, tips, links to other resources and whatever I can find to help you be in control of these years. In my next post I will dive into the positive reasons people may want to delay their retirement.