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5 Dream Jobs for Your Retirement

Category: Work and Volunteering

August 12, 2014 — OK, it’s a little bit of an oxymoron to put jobs and retirement in the same sentence. But we are not talking about full-time employment, we mean part-time or flex-time jobs. We also don’t mean for this article to be a one way stream of information – our hope is that our members will contribute their ideas on dream retirement jobs – both the positions themselves and the criteria that make for a great gig. We also recommend our Blog series on Adventurous Baby Boomer Retirements, where we’ve posted multiple profiles of fascinating, and off-beat retirements.

Criteria for dream jobs
Here are some criteria that we associate with dream jobs:
Flexible schedule. You are retired, so who

wants to be a slave to someone else’s schedule. Sure, if you want seasonal work you might have to work long stretches in the peak season, but then you’ll have plenty of time off the rest of the year.

Has to be fun, or at least interesting. If you are retired you’ve probably had it with a job or a boss that kept you singing “Take this and job and … it”. We are looking for jobs that if not downright fun or engaging, are at least interesting enough to make you want to report for duty.

You get something out of it. That something might be a paycheck – or it might not be. If it is a volunteer job, you get to feel like you are helping other people or a good cause. Perhaps the wage isn’t the greatest, but maybe you get great discounts, a free or discounted place to stay, or special privileges.

5 Dream Jobs for Retirement
Here are our suggestions for 5 dream jobs. We’d love to hear yours.

1. Spend a day in the park. The New York Times published an article, “Learning to Make Work More Like Summer Camp“, that listed many great jobs that baby boomers are enjoying. America’s parks (local, state, federal) are mostly examples of seasonal businesses. They need lots of workers during the high season. Which makes it tough to staff for them and ideal for retirees, because non-retired people don’t care to work only 4 months a year. Aramark is one of the companies that has some of the biggest park concessions. Most of these jobs are outside and in beautiful locations!

2. Mail order company/seasonal employment. LL Bean, Amazon, and many other giant companies do a tremendous percentage of their business in the weeks leading up to Christmas. Some of these companies actively recruit retirees, many of whom move temporarily to areas near fulfillment centers with their own RVs. They get a free or discounted place to stay, and plenty of work for a short season. See: “Holiday Season Turns RVers into Workforce“.

3. Be a travel guide. Like to travel, and have experience? Why not get paid to do it, like Leanne Robinson does for Road Scholar. Leanne, who works as a part-time tour guide, was just one of the boomers profiled in the Times article. Companies in the travel, hospitality, and entertainment business like ski resorts, tour operators, amusement parks, and summer resorts need lots of workers who can fill in at peak times. They offer a variety of jobs, some of which might be perfect for your skill set and interests. Our friend Bill bought a used tour boat – now he takes people on tours of the coastline here in Connecticut. He gets out on the water and gets a kick of meeting new people too.

Skip Budge, who started a business driving cars to FL

4. Turn your hobby into a business. Can you repair bicycles like our friend John, who operates a small bike repair shop out of his garage? Our friend Bob takes people on garden tours. How about doing home or computer repairs for the many people who are starved for someone to fix their stuff? If you live in a place that has seasonal residents, offer to check their houses while they are away. Pet-sitting or dog walking are great for folks who love pets.

Mary Anne Johnston in Guatemala on Rotary literary project

5. Be a volunteer. Write down what interests you, for example: helping sick people, mentoring/tutoring young people, taking care of abandoned animals, working in a library, reading or talking to senior citizens. We profiled Barbara Traynor’s exciting adventures as a professional volunteer in our Adventurous Baby Boomer series. Once you decide on what interests you, start looking around or ask at the Town Hall what organizations in your area are looking for help. You probably won’t get paid – in dollars anyway, but you will get psychological benefits that might be worth a lot more.

Bottom Line
Working on your terms in retirement might be just the thing to round out your life, and put a little more money in your pocket. But just don’t take any job – there are too many good ones to settle for one that doesn’t meet your terms.

Comments? Please share your thoughts – both about the criteria for your dream job in retirement, and what those dream jobs might be.

Further Reading:
Best Places to Find Work in Retirement
How to Find a Job in Retirement That Suits You
Our Adventurous Retiree Series (multiple profiles of interesting retirements)
Should You Start a New Business in Retirement

Posted by Admin on August 11th, 2014


  1. I decided to start a business BEFORE I retired so when I do retire, I will have it well under way. I started a travel assistance business to help people who want or need to travel, and may be alone, get to their destinations. Many adult children cannot just leave their jobs to go get an older family member for celebrations, vacations etcI get them to their family safely we assist in navigating airports and train terminals. I also will travel with the client to their winter and or summer home, get them settled in and come back for them when they are ready to go back. I have a nursing background however this is a non-medical service and as my business grows I will be hiring mature workers. My website is for anyone who is interested.

    by Jennifer — August 12, 2014

  2. Here are three more suggestions….
    About 5 years ago, I did turn my hobby of roasting coffee beans into a business. Along with a partner we put an initial $1,800 each into it and never put another dime of our own into it. After three years, we were grossing over $50,000 a year in sales and having fun! It was the first time either of us had done anything like this. I ended up selling my half of the business to my partner because I wanted to be able to travel more, especially in te winter.

    Seven years ago, i retired from the corporate world. I found a part time job at one of our local golf courses, working in the pro shop. After working at a high pressure job, it was quite a change of pace. One of the benefits was all the free golf, including carts and range balls I could stand. Basically, a free membership! I still do this two days a week.

    Do you ilke the opportunity to pick your jobs when you want to do them? Ever wished you could do something about customer service in different businesses? I have a suggestion for you. In the last six months, I have started performing mystery shopping. From businesses like restaurants, home improvement stores, auto dealerships, golf courses, gas stations, you can get paid to act like a customer and interact with these businesses and fill out questionaires. Not only do you get paid (not a lot) but you get to enjoy reimbursed meals, etc. i even had an opprtunity to go to Grand Cayman for 5 days to mystery shop the entire experience, from airlines to taxis to hotels, etc…all reimbursed. Unfortunately, I could not time it right to go. Once you are signed up with companies, they will email you opportunities in your area. I even recieve phone calls asking if I can perform a mystery shop. I actually feel that I am helping to improve customer service with my feedback. If you are interested, start your search at

    by Bill Yoder — August 12, 2014

  3. Jennifer ,

    Sounds like a great idea

    by Bob — August 12, 2014

  4. @Jennifer — a very interesting concept. I presume you live in a large metro area near lots of airports? (e.g., New York/NJ etc?) How broad are you thinking of reaching out, geographically, as you consider hiring retirees? I presume the entire cost of the companion’s travel needs to be covered by the client, as well as the fees for the service itself. Quite an upscale demographic! Kudos to you….hope to hear more about how it’s working out, as you expand.

    by Paula — August 12, 2014

  5. Paula:

    I am very broad thinking about reaching out geographically. I have found that a travel companion is cheaper than a single supplement when one travels and the service I provide is for those who have no one to go with them and yet they want or need to travel. It is a needed service and will be more so in the future as more families continue to live apart or have busy schedules–to busy to take time off every time their parents need to go somewhere. I make sure they travel safely and get to their destinations with as few complications as possible. I live in Washington, DC

    by Jennifer — August 12, 2014

  6. Working from home” sounds like a scam, with visions of stuffing envelopes, purchasing start-up kits, or buying work-at-home directories. Not anymore. In fact, there is a name for this type of work: homeshoring. Think of a call center where employees (or sometimes people are independent contractors) work from home. An example? Alpine Access ( Marie V. contributed an anecdote to my book about doing this kind of work (as a tech support representative for a cell phone company). As Marie says, she can “stay connected, earn money, and enjoy the comfort and security of working from home.

    by Jan Cullinane — August 13, 2014

  7. I tried the mystery shopping route based on an e-mail I received from a so called HR department. After giving all the required information I eventually was told I would be required to make a purchase of a pre-paid visa card at two pharmacies in my area. They even had the exact address of these pharmacies. They sent me a cashiers check for about $2,000 I was to make two purchases with this check and my pay would be the remaining $170. Before I went to my bank to cash the check I called the bank that it was drawn on and was told based on the routing numbers and other information I gave them the check was counterfeit. I contacted the person that sent me the chack and, no surprise, never heard back. Be careful when someone wants you to cash what looks like a legitimate check to use for a mystery shopper purchase. You could be out some of your own cash. I sent a copy of the check to the bank and the FTC hoping there would be an investigation but have not heard anything back

    by Mike M — August 13, 2014

  8. I found a part-time job pet sitting. I work for a woman who owns a company locally. Her company is bonded and insured. I get 65% of what she charges her clients, and my two-week pay check averages about $700-800. The hours are great, and the dress code is better. It’s my ideal part-time retirement job!

    by Kate M. — August 13, 2014

  9. sorry…but trying to find an ACTIVE (hiking guide) job etc is virtually impossible at a nice location like Nat. PK etc
    I am very active athletic etc but any jobs that are made available to me are driving van , running a concession stand etc because of age>65 despite my abilities and fitness
    In addition there is very little housing near these areas and the good jobs are taken by local folks who retired there and have a nearby cabin or can afford a livable RV

    the interesting & active jobs are gobbled up by students and aspiring NPS rangers etc

    there is, unfortunately a reality in the older workers get the boring sedentary jobs because they are judged by stereotypes and there is plenty of younger competition 🙁

    by Ingrid — August 13, 2014

  10. Jan, there are scam companies out there, but there are many reputable companies that do this. The only cost is typically a $1 purchase, 2 gallons of gas, or the price of a meal. All of these are reimbursed. If a company asks you to deal with thousands of dollars, tere is something wrong.

    by Bill Yoder — August 14, 2014

  11. I am currently helping my 83 year old dad navigate the complicated path of securing home care, getting doctors to talk with each other, physicial therapy and making sure his house is safe. He has limited mobility but mentally very sharp. I am familiar with the medical care process and wonder how inexperienced family members manage this transition. So many details and I live out of state.

    Could this be a retirement opportunity?

    by Lee Anne — August 14, 2014

  12. Both my parents were in hospital before passing away, both were in their late 80’s. My Mom had a stroke and could not speak for herself, my Dad was sharp as ever until a couple of days before his passing. My sisters and I acted as their advocates in the hospital, with the nursing staff and communicating with the doctors as our parents seemed unable to speak for themselves. I realized that this is a needed service for those who don’t have adult children or their children might simply be too far to help on a daily bases. I’m still working (for another 18 months) but might just put this idea into motion once I “retire.”

    by Barb — August 14, 2014

  13. Barb that sounds like a good idea as there are many elderly with n family living close. I love to travel and have checked into becoming a travel agent but the requirements are many. Maybe I will check into helping a travel agency once retirement gives me more time.

    by Wendy — January 4, 2015

  14. Hi all,
    I am within 19 months of retiring from my job. I am excited and grateful. I have been singing since I was a teenager. I decided I would record a gospel CD in 2014. It turns out I learned my mother and best friend was dying of cancer. Decided to turn the loss and anguish I felt into a dedication CD in mom’s honor. I have been able to sale 320 of the 500 CD’s I ordered to date. I wrote a check for $10,000 and donated the sales from the CD and other money to an endowment scholarship fund in Mom’s honor… linking Big Brothers, Big Sisters, college I attended for undergrad, and VA. Mom volunteered with Big Brothers Big Sisters for 26 yrs. So I want to assist children enrolled in the program with accessing scholarship funds for college.
    I love to sing, help others, and give back. I am working on my second CD. I plan to begin another scholarship endowment in another state and have fun singing, meeting people, linking businesses that help others, and giving back. I have gained a lot of ideas for other retirement jobs from the other responses. Thanks everyone!

    by Virginia — September 4, 2015

  15. Mike M. I have a similar story to yours. I responded to a job offering on Craigslist and it was for a Personal Assistant job working from home. What it boiled down to is this person was going to buy me a laptop, printer and other supplies I would need to work from home. The person would send me a ‘check’ to buy this stuff. I emailed the person and told him I changed my mind and was no longer interested. Truthfully, I never thought this was legit from the get go but I waited to see how it played out. He sent me a check anyway even though I told him I was no longer interested. Initially the check was supposed to be around $1,000 to buy this stuff but he sent a check for around $2,000. I was to deposit the check, buy the stuff and send him back the difference which would be around $1,000.I never took the check to the bank because it was just too fishy. I did take the correspondence and check to the police station in my town and the officer was totally not interested and basically says there is no way to catch them! By the time they try to investigate the scammers they have moved on. Glad I have a few miles on me and could see it was too good to be true. I also saw a show on Dr. Phil where a woman met some guy online and they ‘fell in love’. He always had a story where he needed money to get him out of dire straights. He would tell her as soon as he returned from the foreign country he was doing business in, and after he settled his problems, they would get married. Well, he scammed her out of her life savings and she STILL believed he was real and they were in love! OH PLEASE! She never met him in person once! Scammers are everywhere…

    by Louise — September 5, 2015

  16. I hope to travel with the family and possibly turn that into an income by working at state or national parks for free rent. I have talked to other campers who currently do that and seems cool. Also house sitting or care taker seems like a fit for us. The Dreamers

    by The Dreamers — October 11, 2016

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