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Fun and Potentially Profitable Side Hustles

Some unusual ideas for how to spend your time in retirement

Dear Friends,

In future newsletters, I will discuss more serious ventures, such as starting an actual purpose-driven business, entrepreneurial ventures, and encore careers. Helping my clients visualize what this can look like is one of my superpowers!

But today, I want to get your creative juices flowing and talk about some fun “side hustles” that you can pursue in retirement. These can be money-makers if you want, or they can give you some passion and purpose for a couple of days a week or for a season. You could use the extra money to upgrade your travels or even donate it to a good cause if you have already planned well financially for your future. Some of these are a bit unusual, but the idea is to get your wheels turning!

This newsletter was inspired by a recent episode of one of my favorite podcasts, My First Million, where they talked about some of these ventures. You can check out the full episode here:

1. Porch Pumpkins 🎃

For my readers with a flair for design. This idea revolves around decorating people's front porches with seasonal or holiday-themed items, specifically pumpkins during the Halloween and fall season. The concept is simple but profitable. The founders of Porch Pumpkins made over $1 million in just eight weeks by offering customized porch decoration services, making it an ideal seasonal side hustle that leverages holiday demand and a knack for decor. You can check out the actual business here: https://porchpumpkins.com/ They are SOLD OUT!

How to get started:

  • Go door to door in your neighborhood or a neighborhood where you think this service could be desirable. Have 3 or 4 photos of examples of what the packages would look like at different price points. Have a few different tiers of pricing. Gage the interest.

  • Her pricing is $1350 for a luxury package, $750 for a medium package and $300 for small.

  • If people are interested, then these are your pre-orders and you can go and buy the inventory.

  • Once you’ve done a few you take take more pictures (with permission), post on instagram and Facebook and start promoting. Get up a quick website as well. Start driving traffic. Word of mouth will also spread among the neighbors!

  • You could also offer an upcharge to dispose of the pumpkins/decorations when the season is over.

💡 This idea could also be adapted for Christmas lights/decorations.​

2. Professional Grievers 😥

For my readers who have theatrical talents. The concept of "professional grievers" involves individuals being paid to attend funerals or memorial services and mourn on behalf of the family or loved ones. This service is typically used to either make the gathering appear more attended or to perform a ceremonial role in the process. Although it might seem unusual, it is a legitimate business opportunity, especially in cultures or communities where large turnouts are culturally significant​.

How to get started:

  • Visit a few funeral homes in your area and inquire if they are using or need this type of service. Make connections with several and you will be attending a steady stream of funerals!

For more on this, here’s a great article that features the first hand account of being a professional mourner: https://www.cracked.com/personal-experiences-1994-i-am-professional-mourner-6-realities-my-job.html

For a less morbid experience, there is also a need for crowd fillers for political events, concerts and other high-profile events. This can also be a good way to see some excellent shows for free. More: https://otlseatfillers.com/seat-fillers-in-chicago/

3. Non-Sexual Companionship as a Service 👀

Loneliness has become an epidemic, particularly among the elderly, as social isolation and the breakdown of traditional community structures leave many older adults feeling disconnected. As people age, they often face the loss of loved ones, health issues, and reduced mobility, all of which can make maintaining social ties more difficult. Research shows that loneliness can have severe health consequences, including increased risks of heart disease, cognitive decline, and even premature death. Despite the growing awareness of this issue, many seniors continue to suffer in silence, feeling invisible to the younger, more digitally connected generations.

This is an example of how you could help with this epidemic and make some money. Of course, it can also be volunteer work!

For my readers who find purpose in meeting new people and being social. This service entails renting oneself out as a non-sexual companion for people who are lonely or need someone to accompany them for social events. One example mentioned on the podcast was Shoji Morimoto, a man in Japan who makes $80,000 per year by doing "nothing." He rents himself out simply to be present, offering companionship for those who might be socially isolated or friendless. Similar services in the U.S. include platforms like RentAFriend.com or companies like Papa, which provides companions for the elderly​.

Although these ideas are not going to be for everyone, hopefully, they did spark ⚡️ some new ways that you can spend your time in retirement. These ideas illustrate how niche markets can be profitable by focusing on specific unmet needs and utilizing personal skills, creativity, or simply being present. What did this spark for you? If you want to chat about how you are going to spend your time in retirement and do some brainstorming together, book some time on my calendar.

Stay tuned for weekly content about travel, health, relationships, identity, spirituality, doing good and starting a new venture as it relates to retirement/the next chapter in your life ✨

Please subscribe and forward this newsletter to others who are thinking about retirement planning or are already retired. Thanks for your support 🙏.

Warm regards,

Cara Gray
Retirement Coach (CPRC), CEPA™️

P.S. If you want to start planning your retirement, set up a time on my calendar for a chat: Schedule a Chat with Cara

P.S.S. If you are curious about my coaching, there are two options to work with me: deep-dive, transformative 1:1 coaching or a 90-minute intensive, quickstart coaching session. Details about both options can be found here.