Help With The To-Do-List

It seems as though each year the list of tasks required to just manage your life gets longer. The pandemic pause had the silver lining of slower pace, fewer errands, and less responsibilities. Enough things are back to something resembling “normal” that to-do-lists are long and there once again are too many tedious tasks demanding far too much time out of each day.

Buying Time From Strangers

Personal Assistance sound like an intriguing idea, but how many of us have the money, time and/or inclination to share all the details of our lives with a stranger … even if they are professionals? If the cost doesn’t get you, the supervision of your helper will. While you can shop around for help with some generally impersonal tasks using Task Rabbit, Angi (formerly Angie’s List) or Fiverr, life tasks are harder to outsource and coordinate.

How do you prepare for the management of these tasks as you age? We are all expecting to become at least a little more forgetful. How many more services will only be accessible with an electronic device? Meds??? Which ones, when, and ooops, I’ve run out of that yellow pill. Meal and snack planning may not be as interesting as it used to be. Details, details, details … doctor appointments, “procedures” and the occasional lunch with a friend.

Downsizing and moving to senior living communities are attempts to simplify life and reduce daily chores. Another alternative that is taking hold in the marketplace is the offering of wrap-around services to residents in units scattered in conventional apartment complexes. Rather than heading to an assisted living or other expensive life plan community, there are choices for singles, couples or several friends to live in attractive multi-generational communities that are easier on the wallet and that foster continued independence.

The ‘Upside’ of Aging in Place

In late 2020, as the pandemic was still further isolating people and vaccines were not yet available, Jake Rothstein and Peter Badgley formed UpsideHOM (pronounced “home”) to, in their words, “destruct the assisted living facility.” The idea came to Rothstein after he noticed that his grandmother and her friends hated living alone but also wanted to stay independent.

Currently in 41 states, Upside partners with carefully vetted, traditional multi-family apartment complexes. Upside works with building operators to access units appropriate for older adults — modifying them as necessary — and then incorporates services into the base price. The end result is a variety of living spaces, from studio to 3-bedroom units, within the apartment complex, which remains multi-generational.

The concept is simple. When a person calls Upside, they can request their own place, or bring friends to room together, à la Golden Girls (or The Odd Couple). The base price includes furnished common areas, cable/internet, utilities, housekeeping, and maintenance. Because not every older adult needs or wants the same amenities, Upside has a list of à la carte services like meal delivery, transportation, entertainment, travel, and leisure concierge services.

Triple Returns: Time, Money and Fun!

Additionally, the base price includes an assigned Upside Manager — basically, a geriatric care manager, someone similar to a property manager but who can help connect you with resources, help you find a new doctor, even change a light bulb and other routine tasks. The Upside Manager also creates custom social calendars for each Upside member, based on what that resident enjoys and/or is passionate about. No two calendars are the same — in other words, there are no “one size fits all” monthly activities that you’re not interested in.

Regardless of the amenities one chooses, the unit and services are managed by Upside, and all payments are streamlined into one bill. Upside reports that its approach results in units that can cost up to 70 percent less than comparable independent living communities. For example, the base price in the Greater Cleveland market is approximately $2,000-$2,500 for a one-bedroom apartment. For a two-bedroom, the price is between $2,500 and $3,500/month.

Upside is a creative response to a serious and growing demand in the marketplace: affordable support services flexibly provided in attractive multigenerational communities. The Goal: To maximize the ability of residents to be independent and thrive in the Third Chapter of Life.

I’m on board! How about you?

Third Chapter Living celebrates, challenges, informs and promotes conversations about housing issues affecting the Baby Boomer Generation. Check out our website to learn more about our work. Our Facebook Group is a resource center with tips and recommendations on navigating those issues. Share experiences with others who are looking for Housing Downsizing Tools that allow them to successfully age-in-place.


  1. Don Karg on January 10, 2023 at 8:27 pm

    Very informative!
    Great to see some creative alternatives in the marketplace. And hopefully more to come.

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