courage to retire

Getting The Courage To Jump

When I was in college, I jumped out of an airplane.

It wasn’t my idea.

A friend talked me into it.  He gave me the courage to jump, and I’ve never regretted the experience.

Be it a jump from an airplane or (more applicable to this audience) a jump into retirement, sometimes you need a friendly push to get the courage to jump.

If you’ve been lacking the courage to jump into retirement, consider today’s post your “friendly push”.

Sometimes, it takes a friendly push to get the courage to make a big jump. Like the jump out of an airplane. Or, the jump into retirement. Consider this your push... Click To Tweet

Getting the courage to jump pinterest

Getting The Courage To Jump 

Creative Writing 101 was my first “serious” introduction to writing.  

It was September 1981, my first semester in college. I was 18 years old and out on my own for the first time, able to live my own life, to make my own mistakes,

To take my own risks.

Bob and I were in the class together.  We’d just met, and soon became close friends (years later, he was the Best Man at my wedding). The professor introduced our “major” project early in the semester, giving us time to prepare and finalize our ultimate semester-ending project:  “The I-Search Project”.  30% of the grade.  A real doozie.

Unlike Research, he explained, I-Search required you to EXPERIENCE something.  To find something that interested you, and go out and DO IT.  Then, write about what you learned.  What a great concept (and one I encouraged my readers to do near the end of my book.  Kind of ironic, now that I reflect on it).

The hardest part was thinking about what you were going to DO.  Again, not unlike retirement.  Interesting, the parallels of a good metaphor.  By now, you’ve guessed what Bob came up with.

“Let’s jump out of an airplane,” he suggested, and the course was set.

As you read the following story, you’ll find parallels in the world of retirement scattered throughout in italics.  I hope you enjoy the approach.  I guess that Creative Writing class may have made an impact on me…

getting the courage to jump into retirement

Getting The Courage To Jump From An Airplane

I’ll spare all of the details of “ground school”, other than state that I can still remember the mantra that was drilled into our head 179 times in less than 3 hours:  

“Arch…Look…Reach…Pull…5 Thousand…6 Thousand…7 Thousand…Look…Pull…Punch”

Even 40 years later, that mantra is stuck in my mind.  We recited it over and over and over again.  First in the classroom, then as we jumped off an 8′ platform as we learned how to “tuck and roll” (that training may have saved my life when I fell off our roof, btw).  Finally, we were to repeat that mantra when we jumped out of the plane.

Develop your “mantra” for retirement.  For me, it’s Manage The Buckets, Maintain Your Safe Withdrawal Rate, Rebalance Your Assets, Monitor Annually, Give Back, Enjoy Life.

We were “jumping solo”, with a static line connected to the airplane to automatically deploy our chutes.  The most important step was the “Arch” when we jumped out of the plane, which would ensure we fell “stomach first” toward the ground to avoid the static line getting tangled around any valuable body parts.  “If you remember nothing else,” said the instructor, “remember to arch.”

The “Look…Reach…Pull” were purely simulations of a “real” jump when we’d actually pull our own rip chords.  The “Look…Pull..Punch” mattered, however.  In the event our chutes didn’t open after 7 seconds, we were to “Look” at our emergency chute, “Pull” the emergency rip chord, and “Punch” the emergency chute out of its bag.


You don’t find many “solo jumps” at parachute schools anymore.  Someone died at the school we attended a few years after we took the class, and today they only offer “instructor jumps”, where you’re strapped in with a professional.

Yes, jumping involves risks.   

Just like retirement.  

Fortunately, in retirement, you have the choice of jumping “solo” or doing an “instructor jump” with a trained professional.  If you’re uncertain about jumping alone, there’s nothing wrong with hiring a professional to build your courage to jump.  Regardless of how you go about it, you shouldn’t retire until you’ve “completed your schooling” and made sure you’re prepared for the jump.  To be adequately prepared for your jump, make sure your schooling includes both the financial and non-financial aspects of retirement.

getting the courage to jump from high altitude

Jumping Out Of The Plane

The class completed, the five students all suited up and climbed into the airplane.  I remember the adrenaline as the revs increased and we took off down the runway.  Bob had agreed to jump first, and I was behind him as the plane climbed into the sky.  The other three students would jump behind me.

Recognize there are always others who will be jumping into retirement behind you.  Be generous, and try to find ways to teach them what you’re learning on your journey.  There’s a reason the byline for this blog is “Helping People Achieve A Great Retirement.”

When we got to the correct altitude (when you’ve saved enough money), the instructor opened the door.

It Was Time.

I was scared to death.  We could barely hear the instructor’s voice over the scream of the wind.  I watched as Bob slid toward the door and let his feet drop over the edge, his jumpsuit flapping in the wind.  As we were trained to do, he reached out for the wing strut and, a moment later…he was gone.

Prior to retirement, I enjoyed watching people “jump out of the plane” before me.  I liked to talk with them in their final few months of work to discover what they were thinking.  How they’d planned for retirement.  How it felt.  Ultimately, it gave me more courage when it was my turn to jump.

The instructor gave me the signal.  It was my turn to jump.  I double-checked my static line connection (make sure you have sufficient liquid assets set aside before you jump into retirement) and slid toward the door.  As I hung my legs over the edge and reached for the wing strut, I was amazed at the force of the wind.  Imagine sticking your arm out your car window at ~100 MPH and you’ll get a sense of the sensation. 

The instructor tapped my shoulder – my signal to go.

Almost everyone I’ve talked to prior to retirement said, “You’ll know when it’s time.”  

I stared down at the ground some 2,500 feet below me, took a final deep breath, and…


I still remember my first day of retirement and suspect I always will.


I nearly panicked as my body tilted 45 degrees, a result of the wind from the plane’s forward momentum pushing hard against my body.

Retirement isn't normal.  It takes some time for your body to adjust.  Maintain your position and enjoy the ride. Click To Tweet

Three seconds in, I suddenly realized I’d forgotten to say the rest of my mantra.  I was supposed to do the “Arch…Look…Reach…Pull”, but I was stuck on Arch.  Panic set in as I lost complete sense of time.  “Have 7 seconds passed yet?    Is my chute going to open? Should I Look…Pull…Punch?  How long should I wait before pulling my emergency chute?

Take a breath when you first retire.  You’ve got years to sort things out, don’t panic.  Just focus on “your arch” (the most important thing) and enjoy the ride.

Suddenly, my body was jerked into a wonderful, powerful swing as the chute opened.  Within seconds, all was calm.  There is, perhaps, no better feeling in the world than the moment your parachute opens during your first-ever parachute jump.  I smiled, then reached up for my toggle handles and glanced up at my chute to make sure the dreaded “Mae West” hadn’t happened to me. 

All was good. 

Very, very, very good.

What had been panic just moments before became one of the most exciting moments of my life.  The reality hit me: I was hanging beneath a parachute, free to enjoy the scenery around me.  Turn left.  Turn right.  Look around.  Oh, that view.

I was flying.

The first few months of retirement are pure bliss.  No more work, no more alarm clock.  You may be flying, but realize your flight will evolve with time.  You’ll be doing this for a long time, so settle in and enjoy the ride. 

I located the landing zone and enjoyed leisurely turns as I floated toward my destination.  I watched Bob descending below me and soon saw his chute collapse as he hit the ground. It felt like I would be in the air forever, but I knew it would only be a matter of minutes until my ride was over. 

Take the time to set up your legacy plans.  You won’t be here forever.  Savor the time you’re given, but also be prepared for your ultimate landing.

Lost in the marvel of the experience, I was shocked to see how soon the ground was approaching.  It was getting closer, and it was coming at me much faster than I expected.  As instructed, I turned into the wind and prepared for impact.

The landing was harder than I thought it would be.  I instinctively did the “tuck and roll” we’d practiced, but still had the wind knocked out of me by the impact.  I quickly regained my composure and started jogging toward the chute, making sure it collapsed before it could drag me across the ground.  Bob and I met up, the huge smile on his face telling me his experience was as magical as mine. We high-fived then headed back toward the hangar, carrying our wadded-up chutes in our arms.

Enjoy your retirement with friends.  It’s better that way.

Fifteen minutes later we were getting our “jump debrief” by the instructor.  He said we’d all done great, but only one member in our class had followed all of the instructions.  I’ll never forget the “Jump Card” he handed me at the end of our session.

“Nice Arch,” he’d written, “But No Pull.”


Getting the courage to jump into retirement takes time.  Don’t be worried if you have concerns, it’s a normal part of the process.  Focus on how amazing that journey can be after you cross The Starting Line, and spend time thinking about the life you’d like to design for your retired years.  No one really knows what life is going to be like in retirement until they live it, but most say they wish they’d have retired sooner.

The jump is scary, but the ride is worth it.

As I write these words, I’m living the best years of my life.  I know they won’t last forever, but I’m enjoying the ride for as long as it lasts.  I’m glad I left that airplane, and I’m enjoying the time that I’m floating under this parachute.  I’m present in the moment, and I’m embracing the experience to the fullest.

By the way, I got an A on that paper, and it was the best assignment I was ever given in college.  I was able to experience something that I’d have never experienced, and it’s one of the best memories of my life. And to think, it never would have happened without a little push.  A push from the professor, and a push from a friend.

Sometimes life is better with a push. 

Worried about retirement?

Consider yourself pushed.

Get out of that airplane.

It’s Time To Jump.

PS – today’s post was inspired by the following comment that Ben left on Retirement Is Like A Game of Poker.  Thanks to all of you who interact in the comments.  I read every one of your comments, and they often inspire new posts…

Your Turn:  Are you scared to jump into retirement?  What’s holding you back?  If you’ve overcome those fears and made the jump, what recommendations would you make to those jumping behind you?


  1. I absolutely need that push. I think I am ready to pull the string – January 2023!!

  2. The good thing is, even if you jump into retirement and find it not for you, you can jump back into the plane and get a job again. Or at least you can go back to working part time or consulting.

    I feel this is something a lot of people who plan to retire don’t really think about.

    With a hot labor market right now, people can do almost anything!


    1. Great point, Sam. Perhaps that would be the “Bungee Jump”? Thanks for adding a great point to the discussion. I’ve got two close friends who recently returned to work, but on their terms. Both are working from home with fewer hours, and still have some of their Freedom while building a bit more of a cash cushion. Nothing wrong with that.

  3. Keep your knees in the breeze paratrooper! Fritz love your story about taking that leap of faith from a perfectly good airplane and comparing it to taking that final step into retirement. As a former trained Army paratrooper, I can relate to your experience. Whether you’re jumping out of a civilian or military aircraft you go through the training, and thus, must rely on your trainers and equipment to become confident. Preparing for retirement is the same. Learn, prepare, and then exit that perfectly crafted plan and enjoy the descent which is one of the most peaceful and lovely moments in life you will experience. I remember the Black Hats at Fort Benning Georgia yelling at us during our two weeks of vigorous training before we first jumped telling us all along that it was “not natural to jump out of a perfectly good plane”. Just like retirement after decades of work it is not natural to just stop work and simply retirement. But with the right preparation both financially and mentally you can “put your knees in the breeze”. I look at you as a Black Hat sergeant with your wonderfully crafted retirement preparation posts and book in preparing all of us to take that final leap of faith into retirement.

  4. Thanks a lot your your inspiring articles! Your words are extremely encouraging. I retired one year ago and I still need some time to adjust to the new phase of my life , but thanks to your blog transition is much smoother!!!


    1. Michaela, and THAT is precisely why I write. Glad my words are “encouraging.” Enjoy that transition, you’ll soon find your sea legs and learn what you’re meant to do in this new phase of life. I’m honored to play a small role in your journey.

  5. Fifteen months ago, I pushed the jump over the starting line up by nearly a year. I had been planning, researching and following your posts for a few years in advance. Like you mentioned in this post, I knew I was ready for the jump and then there I was! For me, the first 12 months was like an extended vacation; before I realized I landed and was exactly where I should be at this point in my life. My only sacrifice is paying the high cost of medical insurance, but with the advanced planning I am able to fit this into my budget. In my case, I feel so much better physically and mentally. I have friends reluctant to retire and let them know that they will know when the time is right for them. Love your posts, thanks!

    1. Lb

      You can see my post below. I would love you input on medical coverage and cost prior to 65, if you are able to share? Medical is my ultimate hurdle. 🙂

      1. Ken, I planned on $12K a year for medical insurance for 3 years to take me to age 65. In advance, I maxed out contributions into my HSA intending on using this to pay premiums if needed. I had always carried my husband on my insurance, so when I expedited my retirement date by 8 months, my planned cost for insurance was more, to cover us both until he turned 65. I stayed on my company plan -unsupplemented. First 8 months cost was $1,350 a month, once he hit 65, my cost is $950 a month plus another $88 for his Medicare supplement. It’s expensive, but for us, totally worth it. We are fortunate to both have good company pensions, and we both took social security early (I know the experts advise not to, but in our case we did what was right for us). We have a nice 401K and so far haven’t needed to use the HSA for insurance premiums. Good Luck, I know the apprehension you feel about paying for medical insurance.

  6. Thank you for this post! It resonates with where I am at in my journey. I gave notice of my early retirement at the end of 2022 and while I am largely focused on a smooth transition with the end day over ten months out when I do step back it is scary. Like you, I went skydiving once (tandem jump almost 30 years ago) and can relate to the experiences you describe of training, fear and exhilaration. I feel all of those experiences when I think about the transition to retirement. I have done a lot of planning and mentally know that I am in solid shape. However, as you indicate there is a big difference between knowing something intellectually and experiencing it, whether it is stepping out of the plane onto the wing with your instructor at 10,000 feet in a real-life wind tunnel and making the jump to stepping out of the safety of a regular paycheck and jumping into the retirement journey. The former worked out well for me and I am optimistic that my retirement training will be even more enjoyable.

    1. Congrats on giving your notice, Gregory. Enjoy those final 10 months, I remember mine well. It sounds like you’re thinking about all of the right things, and I’m sure you’ll be ready when it’s your time to jump. Enjoy the ride!

  7. Fritz, You are post is very timely for me. I have a date on the calendar for “my final day” but the closer it gets the more I am getting symptoms of “one more yearitis” My concerns are not rooted in my lack financial planning, or even my lack of post retirement plans, but more on leaving my accounts, and many good colleagues and customers behind. The hardest thing about departing when you work in sales is that you seemed to get involved in more long term projects that won’t pay off until after your final day has come and gone…..ughhh.

    1. MAI, I’m glad the post resonated with you. No doubt, leaving those relationships is one of the harder parts of retirement. In my case, I had many friends who I’d known for decades. I can relate. The best thing I did was to get involved in charity work prior to retirement in our retirement town, it gave me the opportunity to start building new “retirement relationships” to replace the ones I lost. The “softer” side is critical, glad to hear you’re thinking about it. Enjoy your jump, you’ll know when it’s time.

  8. Great article. I’m really struggling with taking the jump. I’ve been over the numbers and scenarios many times and was ready a year ago (beginning 2021), but I decided one more year and now I’ve pushed it out to April 2023 (I want to secure my bonus). The fear is real.

    1. Nancy, there’s nothing wrong with “One More Year” (I did it myself), but don’t let it become OMY, then OMY, then OMY…

      Drawing a line in the sand (April 2023) is a great way to commit to the jump. I did it myself, and the jump went smoothly. Hoping the same for you. Fear is real, but can be overcome.

  9. Fritz – thank you for the timely post. I also did a solo jump 30+ years ago and reading this was like reliving that experience. Yikes! Oh crap! Fun! Well, I am sitting on the edge of the airplane again because I am jumping into retirement in 6 weeks. Yes, I am nervous and excited. Your blog and posts are a great source of information and resonate with me. Thanks for the nudge!

  10. It’s spooky to jump.

    The worst thing is some occupations, once you leave, you can’t go back (currency issues).

    Like anesthesiology….

    (and, the fear of “what happens if….” stays with you)

  11. I had a skydive planned and ready to go years back and then my job sent me on an international trip that made me miss it. My friends went and I didn’t and I was upset, but I also got to go to Korea which was cool. As for the retirement jump, I’d consider that much harder because there’s so many more factors involved – identity, value to society etc. No one is thinking of their identity when they jump out of an airplane, it’s just an acute fear. Retirement brings up more ‘chronic’ fears.

  12. This blog post is very timely. As a former skydiver in my thirties (it was the biggest adrenaline rush ever) I am now in that place where I would like to take the next jump into retirement. I am not 100% sure about the financial aspects though the “models” say “we’re fine”. My work is very stressful and I am getting less and less tolerant though I also appreciate the gifts and connections at the same time. Like you said I’ll know it in my gut when I am ready so I’ll wait for that signal “to jump”.

  13. I was “pushed” into retirement by a layoff. My plan was to work for another 3 years, but that push was one of the best things that ever happened to me. After the initial shock of it all and a 3 minute cry with my wife, we were happy as could be. We phoned our financial planner and he said we were in great shape and not to worry about money. The other fortunate thing was that I had just turned 65 and, with my wife a year older, we were able to get right on Medicare after the 90 day grace period on my company medical plan expired. Since then life has been great and I am actually grateful I was laid off. All those years of working and saving and the timing of the “push” were all lined up perfectly.

    1. Roy, glad to hear that early push worked out for you. I’ve heard from numerous friends who have also stated, in hindsight, that getting “pushed out the door” ended up being the best thing that ever happened to them. Enjoy that view during your parachute float…

  14. Great post — the jump analogy is perfect! I haven’t sky dived but I have taken the leap into retirement — and it certainly felt like a leap! You’re so right that you know when it’s time. Still, it takes work to build a retirement life that will work as you need. Planning is very important, but be prepared for surprises too!! Thanks for a great post!!

  15. Just started reading your Blog and I loved your book. I am about 6 months out and it is stressful. I feel comfortable financially and have spent the last year or so getting comfortable with the softer side of things. Some days I cant wait and some days I’m scared to death. At some point I will need to jump. I appreciate the encouragement.

  16. Excellent article. Thank you

    Like others, I have run the numbers and get a “green light” to jump into retirement. But I continue to feel very unsettled with health insurance coverage and costs prior to 65. ( I am 60 and my wife is late 50’s).

    COBRA only bridges us so far. ACA coverage (quality of coverage) appears to be uncertain to me.

    If anyone has great advice to overcome this hurdle, I would be so very thankful. Because I would “jump”. 🙂

  17. Fantastic article! I love the parallels between skydiving and retirement. I “jumped” 10 months ago and have no regrets. One sentence in the article that got my attention: “It is felt like I would be in the air forever, but I knew it would only be a matter of minutes until my ride was over.” For those that are unsure about taking the leap, remember life is short. Take the jump and enjoy the scenery!

  18. When you push past the fear, a whole world of opportunities reveals itself to you.

    I really enjoyed this blog. It reminded me of why it is so important to challenge ourselves to experience something new, something hard. It helps us to build our confidence to explore and do other ‘hard’ things in completely different areas. Fear will keep our world small and courage can be learned, one small thing at a time.

  19. Great post Fritz, and a really cool story. Beginning my eighth year of retirement and I whole heartedly encourage anyone who is ready to jump to make the leap of faith and go for it. I can’t express how wonderful it is to wake up every morning and feel like you are 10 years old again and it’s the first day of summer vacation. Keep up the good work Fritz, you are an inspiration to us all, Thank You!

  20. Great post Fritz! You have a gift with words for sure! This is where I am at for sure – retire this year or next?! Change is scary. Will I have enough? Enough money. Enough to do. So many questions! Thanks for the post and the push!

    1. Thanks for the kind words, Cathy. Funny that I never knew I loved writing until I started this blog at age 52. I started a blog (scary change) and found something I love. Kind of like retirement. Make that scary change. Make the jump when you’re ready. The fear never goes away until that parachute opens…

  21. Thanks for the article Fritz. I consider myself pushed forward. I feel like my finances are a big lump of clay just waiting to be sculpted into three buckets. How did you start that process? I will most like retire within 6 – 18 months and am not sure how to put my house in order so to speak. Any suggestions? Did you do it all on your own or did you have a financial advisor?

    1. Rob, you’re at a good place (6 – 18 months) to begin the process. The most important initial piece is to start building liquid cash reserves equal to 2-3 years of spending. You’ll want this in place by the time you retire, so best to start now and begin building it up. I outlined the whole process in my post, “How To Build A Retirement Paycheck From Your Investments.” I did it 100% DIY, but I really enjoy this stuff. If it intimidates you, no problem hiring a professional to help you out. Hope the article helps, best of luck as you approach The Starting Line!

  22. My jump is scheduled for March 11!! Thanks for the ground school instructions the last few years.

  23. Fritz, just got your name and blog from a close friend, and really enjoy what I have read so far. I am just about to turn 59, love the company I am working for, and love the work I do…..however, the prospect of being able to walk across the street and sit on the beach while reading my latest book at any time… really starting to call my name! I have opened the “retirement conversation” with my financial advisor and so we are starting down that road. I could definitely hold out and keep doing what I do with this company until 65, but we are talking possibly earlier. Myself, I know that medical coverage will be a big item to bridge the time until Medicare, but wondering what other items might I think about and prepare for that would be similar to medical coverage.

    Always wanted to parachute….maybe I might put that back on my bucket list! Thanks again for all you do for us “almost retirees”!

    1. JPT, glad to have you aboard. Good for you for starting to ask the right questions when you have time to adequately prepare. Hard for me to pinpoint any particulars for you, given that I’ve written ~300 articles on the topic, but the two biggest things I’d suggest are:

      1) Recognize how big the shift is from “Accumulation” to “Withdrawal”.
      2) Focus as much time on planning for the non-financial as you do the financial.

      Hope that helps – best of luck on your journey to “The Starting Line!”

  24. Hi Fritz, Five years ago I went up in a huge hot air balloon at Albuquerque, New Mexico Balloon Festival. What an experience! Still bringing a smile to my face.
    You closed the comments on your drawdown revisited and I wanted to say I look at taking the pension earlier a little differently- it means your many years of dedication to one company gives you for the rest of your life the money for your taxes and health care and more. Every year you live-, the over all compensation From your loyalty and hard work increases dramatically. The younger generation doesn’t have pensions. We are blessed. 24 years of retirement and still jumping into new interest. Sincerely, Lara

    1. Lara, the hot air trip is a bucket list item for me, that’s always appealed. Cool that you were able to experience it.

      As for pension…amazing minds…I’ve had that exact same thought many times since I’ve retired. The pension truly is ongoing compensation for three decades of dedication. No wonder companies don’t offer them anymore.

      Sorry about the comments being closed. That happens automatically (after 2 weeks, I think). I was spending hours responding to new comments on old posts, so decided to take that step to keep my sanity.

  25. You were never coerced into “Let’s jump out of an airplane”.

    You did not know what do with your extraordinary potential at such young age…

    And the idea of …jump out of an airplane… seemed to be on par at the moment.

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