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Are You a Failed Retiree? Check Out These 5 Fun and Profitable Business Ideas

By Kim Neumann August 01, 2023 Managing Money

Oh, blissful retirement! Is it a reality or is it a myth?

You planned it all out – endless vacations, hobbies you finally have time for, and no alarms ringing at the crack of dawn. And voila! You finally retire!

But instead of relaxation and joy, you find restlessness and boredom knocking on your door. Or, you may have just discovered that the retirement savings weren’t enough to sustain the lifestyle you dreamed of. Or worse still, you might be missing the routine workplace hustle, the purpose, the morning coffee interactions.

If any of these signs are squeaking louder for your attention, you may have fallen into the quirky category of ‘Failed Retiree’.

Fear not, you’re not alone, and it’s not as dire as it sounds. It’s merely an inner alarm sounding off, telling you it’s time for…

Retirement: Take 2!

Kind of like a do-over, Retirement: Take 2! is where you reintroduce elements of work, social interaction, or new habits to create your version of retirement.

To assist you on your new, exciting journey, I’ve got 5 fun and profitable business ideas for your consideration. Use these to get your own creative juices flowing, or grab one and take it for a spin.

What Makes These 5 Business Ideas Fitting for Failed Retirees?

I’m glad you asked! A few reasons:

They’re Unique

I put a lot of thought, marketing insight and even some brand brainstorming into each of these business ideas – by standing in your shoes.

They’re Profitable

Each of these business ideas meets my criteria for being specific, practical, and – cha-ching! – profitable.

They’re Flexible

One thing’s for sure: you don’t want to be chained to a desk all the livelong day, now that you’ve graduated to retirement!

They’re Enjoyable

Whether it’s teaming up with friends or getting in steps with a furry companion, supporting local businesses or meeting new people, these ideas pull together other enjoyable aspects of daily life.

And finally, for each of these business ideas, you’ll find resources such as articles and online courses to expand your knowledge and training, along with marketing tips to make your business stand out as THE best choice in the crowd.

Now let’s dive in!

Idea 1: Virtual Marketing Assistant for Life Coaches

The coaching industry exploded over the last 10 years, with approximately 23,000 certified life coaches in the US today.

New coaches in particular need help promoting their services and growing their client base. As a virtual marketing assistant, your job is to execute the marketing plan, not devise one. So pressure’s off there!

The most effective digital marketing activities for coaches include email marketing, guest blogging and social media marketing. These tasks also happen to be time-consuming, and not so easy to outsource.

By specializing in marketing services tailored specifically to coaches, you can position yourself as an expert in this niche yet sizable market and attract clients who need a reliable, skilled and resourceful marketing VA.


To get acquainted with the terrain, I recommend Coach Pony’s free Couch Training guide.

For free online training, check out The Virtual Savvy.

Marketing Tips

  • Offer three distinct service packages tailored to new coaches and spell out exactly what each package delivers.
  • Consider offering a free sample of work needed (within reason – keep it under a couple hours of your time) to showcase your value and build trust with potential clients.
  • Develop relationships with coaching organizations or associations to increase referrals and build trust.
  • To reach a wider audience of coaches, run a sponsored ad on LinkedIn. I recommend a video that shows you talking about your services, and how you can help.

Idea 2: Nonprofit Multitasking Extraordinaire

Sure, you could market yourself as an “admin assistant” or “operations manager.” But a multitasking extraordinaire? Now we’ve got a real picture of who you are and what you’re capable of! This is a great example of shining your own beacon of professional light in a sea of so-so sounding prospects.

I’ve worked with a couple nonprofits myself and can attest to the fact that multitaskers are deeply appreciated. Throw in “resourceful, creative problem-solving, passionate team-player” and you’re really speaking their language!


Since many nonprofits are funded by memberships and donations, I recommend getting acquainted with popular membership management platforms such as MemberClicks, Classy and Wild Apricot. Try a demo or free trial to get familiar with this type of software.

Read up on all-things-relevant to nonprofits. For example, Wild Apricot’s blog is brimming with resources on marketing, organizational management, and fundraising ideas.

Marketing Tips

I recommend these two simple steps for landing a client or two:

Research Nonprofits You Want to Work for

You may already have an idea, but also check out sites like Charity Navigator and VolunteerMatch as well as local or smaller nonprofits that might not make these lists.

Write a Warm Outreach Email to Each One

Mention why you’re reaching out and detail a few ways you could help. Be totally honest – even mention you’re a “failed retiree” and want to put your skills and passion to use, but only for the right organization. Keep it short, and personable. Follow up in two to three days.

You might be thinking… Hey, wait a minute. This sounds like a job I’m applying for. But it’s not – it’s a service you’re offering. It’s up to you whether you call yourself a freelancer or a business owner (they’re really one and the same) and ultimately, you need clients to be in business, right?

Idea 3: Financial Advocate for Seniors

I just heard another – YET ANOTHER – story in the news about senior fraud.

You know this already – older adults are especially vulnerable to scams. In fact, over a quarter of financial fraud victims are over 60, according to the FTC. Coupled with that, seniors often struggle with managing their finances and navigating the complex world of retirement planning.

Here’s where you can help – not as a financial advisor (unless you hold the proper credentials, of course!) but as a financial advocate, someone who is chosen to manage money matters, such as paying bills, managing property, and handling taxes. A financial advocate may be a paid professional, or a trusted friend or relative.


For this idea, I recommend exploring the National Counsel on Aging: Connect, You can become a facilitator using toolkits and guides offered here. For example:

Khan Academy’s Financial Literacy also offers life skills on detecting scams and fraud.

Marketing Tips

  • Consider the outcomes you want to help seniors and their families achieve, such as peace of mind, along with financial wellbeing, safety and security. List all the ways you can deliver these outcomes, in both group and one-on-one roles.
  • Network with local senior centers, retirement communities, and organizations catering to seniors.
  • To establish yourself as a compassionate and skilled resource, offer free informational seminars or workshops that include takeaways on how to identify fraudulent calls, emails and text messages.
  • Network with other professionals like estate planners or elder law attorneys.

Idea 4: Dog Walking: Fitness and Fun, Rolled into One!

If you live in a dog-friendly neighborhood like I do, you’re basically surrounded by potential furry clients!

And, if the idea of getting dragged through the hills with a Rottweiler isn’t your cup of tea, you can be choosy. Want to be an exclusive walker of lapdogs? Anything is possible.


While many cities don’t require any special license or permit to walk dogs, you’ll want to check with your city or county for local license requirements.

Consider taking a First Aid Class for pets. The Red Cross offers this class online ($25). Try Googling “pet first aid and CPR class near me” to find other training options – preferably in person so you can ask questions, meet others and network!

Marketing Tips

  • Since this is a hyperlocal kind of business, you needn’t market your services any farther than you’re willing to go. Posting at grocery stores, pet shops and dog parks (if allowed) in the neighborhood can get the word out effectively.
  • If ever there was a perfect website for those seeking a trusted local to walk the dog, it’s You can even start by searching “dog walker” and responding to people looking for your services.
  • Try offering your services on Craigslist if you’d like to cast a wider net.
  • To boost your income potential, consider offering additional services like house sitting and doggy daycare. We’ve hired an actual babysitter off of to watch our pup while away at the beach. I’m guessing ours isn’t the only pup with a severe case of separation anxiety who needs this kind of attention!

Idea 5: Local, Caring Customer Service

Ah. Remember the days when you called customer service and someone actually picked up the phone?

I predict a return to those days. Maybe not for the Comcasts and the Verizons of the world, but for local businesses that want happy, repeat customers. Well, YOU can be that service!

This is a slightly less flexible business idea, assuming your services would be needed during normal business hours. But it’s certainly a “work from home” option, and if you team up with a couple friends, you can alternate shifts, and maybe even build a fun and lucrative business together.

And just remember, you offer clients something the competition simply cannot: friendly, personalized answering services by and for locals!


Here’s a great article by Grasshopper, a virtual phone software.

If you’re less interested in running your own business, check out openings at Back Office Betties, ReceptionHQ, and my personal favorite, Ruby.

Marketing Tips

Identify real businesses in your area you’d like to serve. Those that risk losing business without a live receptionist include: home improvement and repair companies (roofers, plumbers), lawyers, veterinarians, and health and wellness services.

Become knowledgeable in these specific businesses by visiting their websites (and their competition) so you can “speak their language.” Look at their Yelp pages to see what customers like (and dislike!).

List all the benefits these businesses will get from your services. These might include increased aquisition and retention, more positive online reviews, and peace of mind knowing they’ve got the phones covered – especially during busy hours, lunchtime, and possibly after-hours and weekends.

Once you land an interview, ask for specific details on how you can help improve customer acquisition and retention. For example, do they need someone to make outgoing calls, for a friendly check-in? Come up with your own ideas to share.

Final Thoughts

Remember, You’re in Good Company

More and more individuals are opting out of traditional retirement and embracing what some call “encore entrepreneurship.” I just love this description, don’t you?

And, according to the Global Entrepreneurship Monitor, a significant number of Americans between the ages of 55 and 74 started new businesses in recent years, driven by a desire to make a difference or build wealth.

Inspiration Is Around Every Corner

I love reading about business success stories – especially deeper dives on how they did it. Here are three women who prove that starting a fresh business venture is possible at any age:

  • Janice Lennard, at the age of 72, started her own brand, Janice Lennard Yoga. She promotes and provides classes for maintaining physical and mental well-being through yoga, Pilates, and ballet.
  • Roberta Kagan decided to become a self-published author in her early 60s. She started her own company, Roberta Kagan Books, and became famous for writing historical fiction and romance novels.
  • Judy Gross founded LightHeart Gear, a company that designs and manufactures lightweight, durable camping gear, at the age of 60. She turned her love for sewing and outdoor adventure into a successful business.

Looking for More Business Ideas?

If none of these five ideas float your boat, consider how your hobbies or passions might transform into potential business opportunities. Are there any other business ideas you’ve had and want to revisit? You may also like to check out my megalist of 81 Business Ideas.

Remember, Retirement: Take 2! is an opportunity to explore, innovate, and contribute in ways you might never have imagined.


Let’s Have a Conversation:

Do you consider yourself a failed retiree? How are you dealing with that? Is Retirement: Take 2! On your radar? What’s your next big idea? We’d love to hear about it in the comments!

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Shari Harris-Dunning

I’m definitely a failed retiree. I spent over 30-years as a civil servant in the environmental regulatory field. I DON’T want to go back to that kind of work, but would love to do freelance/contract work in the environmental/sustainability/climate change field. Problem is that I’ve been out of that profession for over 5-years and lack some of the savvy web skills, AI, web-design, marketing skills that seem to be in demand. After retirement, I went back to school for my AAS in massage therapy — and yes I am an LMT, but am very tentative to work for a spa or health care facility in that the hours are long, the massages are back-to-back and it can be grueling. I have a little set-up at my home, but I live in the country so it’s kind of challenging to get clients. So, I’m a failed retiree who is spinning her wheels…

Kim Neumann

Hi Shari, I think you speak to a pretty common theme for people. Spinning wheels (btw, been there, plenty of times!) is a perfectly good place to start. Also, knowing what you DON’T want – that’s huge. I’ve found it helpful to write it all out – all the things you DO want in one column, and DON’T want in the other column. I find just getting it all out on paper gets things flowing.


My husband has already decided he’s not retiring. He was self employed in a business we owned before going back to becoming an employee. This was purely because he was offered something he couldn’t refuse in his late 50s, both financially and relating to his sought after experience. He plans to work for his current employer until retirement, then we’ll return to our home country and he’ll set himself up as a Consultant. I’ll be seeking an online job I can do remotely with hours to suit myself.

I have a bachelor friend who’s 82, he still works 4 days a month in his old job as front of house in a gallery. He enjoys the contact with the public and the money he earns pays for his love of theatre, film and travel. In a previous life he was a professional theatre actor and still takes on small roles when they come along. He also does paid work as a film and TV extra from time to time.

My view is if you want to keep on working and are capable you shouldn’t let anything stop you. I’ve seen too many people who’ve retired and given up, sadly one is my own brother. He retired way too early at 59 and at 73 is completely lost.

Kim Neumann

I really appreciate what you’ve shared here, Linda. All three of your real life examples (plus your own) attest to the importance of how to / “if to” retire. Thank you for reading my article and happy unretirement to you both!

The Author

Kim Neumann is a one-woman marketing agency based in Marin County, California. With over 20 years of experience and a Master's in Traditional Chinese Medicine, Kim weaves wisdom into actionable advice for DIY business owners at When not strategizing, she enjoys time with her family and spicy Chihuahua, Fonzie.

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