How to Retire Successfully with House Sitting

4 Jun, 2023

How to Retire Successfully with House Sitting

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HouseSit Match’s blog editor recently sat down with Pauline Field, an experienced coach who helps women on the brink of retirement discover how to retire successfully.

Discover How to Retire Successfully by House Sitting

Edited by Kelly Hayes-Raitt

Hi, Pauline, thanks for being a new member of HouseSit Match! You’re a coach who helps women discover how to retire successfully. What challenges do women face? 

For many women, the first challenge is whether they can afford to retire. Will they be able to have a reasonable lifestyle if they retire? Will they have enough money for the unpredictable things, healthcare in particular. Will they have to work for more years than they would like? Will they have to work, at least part time, if they want to retire?

How to retire successfully
Pauline in her car that matches her hair!
Photo Courtesy of Pauline Field

There are other major questions many women have about how to retire successfully, perhaps the biggest of all are: What will I do? How will I find meaning in my life? Right behind those questions are: Who will I do it with? and Where will I live?

How are these challenges different from what men face?

The biggest difference for men is the financial aspect. They usually have earned more, have not taken time off to raise children or care for aging parents, and have often been making the financial decisions, so they are much more prepared.

The biggest challenge for men is answering What will I do? How will I find meaning? Their identity is so much about what they do in their career that retirement looks like a black hole.

House Sitting Helps You Discover How to Retire Successfully

House sitting was instrumental in helping me figure out how to retire successfully. What advice do you have for women who are searching for their ideal retirement destination?

House sitting is a terrific idea and you are a great role model. The pandemic opened our eyes and minds to the possibility of living in another country. More people than ever before are considering such a move. Deciding where to live – and particularly moving to another country – takes a lot of thought and research. It is a major life-change.

I recommend to first do some soul-searching. Why do you want to move? What are your basic values and priorities? For example, do you value climate over transportation; good healthcare over knowing the language? Do you want to live in a safe, urban environment or in a peaceful, rural setting; by the mountains or near a beach? Knowing what you really want and need will help you create a life that makes you smile.

How to Retire successfully
Pauline enjoying the Lisbon breeze while vacationing in retirement.
Photo Courtesy of Pauline Field

There are so many things I wish I’d considered as I was figuring out how to retire successfully. For example, I wish I’d spent more time on long-term financial and tax planning – especially as it relates to relocating to another country. It should be part of our retirement calculator.

I mean, now that I’m dipping into my investments each month, which accounts do I tap first? Do you have a magical checklist of things women should consider as they near retirement to discover how to retire successfully? Can you spill a few secrets?

Although everyone’s retirement vision and circumstances are different, there are some basics that are important. Once you have decided that you want to retire and are considering where to live (either in another state or in another country), I would say, make your own magical checklist of what would be your ideal location. It helps you find a purposeful life after retirement.

Make a list of the “deal breakers” that would have you say no to a particular location.

Visit the places you are considering at least once – twice or three times is better. This is where HouseSit Match is a boon. You get a much better sense of the community when you are in the neighborhood than if you are staying in a hotel.

Find an expat group for the area on social media and browse their comments, ideas, hiccups they have encountered – as well as what they love about it.

As you mentioned, do check the financial aspect – the cost of living, the cost and quality of healthcare, the tax considerations, the cost of visits back to the U.S. If you just look at the basics of what it will cost you each month instead of looking at the whole picture, you could find yourself running into financial trouble down the road.

Coaching Women to Help Them Learn How to Retire Successfully

How did you get into coaching women on how to retire successfully? Is there something you wish you’d known before you embarked on your own semi-retirement path?

A client from my management consulting career had asked me to coach her on retiring because she wanted to retire but had a lot of anxiety about it. When she was happily retired, she mentioned there are many other people like her who could use my help.

As I love coaching and was looking for something more to do in my own retirement, I jumped on the idea. I dove right into researching how to retire successfully, looked at my own experience, and put Coach4Women together.

How to Retire successfully
Enjoying life with hubbie on their 25th anniversary
Photo Courtesy of Pauline Field

There is much I wish I’d known and which I’ve learned mostly by trial and error – and I am still learning, by the way! As I have retired 3 times, I have had the opportunity to see what I was missing and what I could have done better if I had been able to find a coach to guide me.

I bought into the societal narrative that retirement would be a 20+ year vacation, doing everything I had always wanted to do. What I didn’t think about was that vacationing loses its luster after a while. While I needed time to decompress each time I retired, when I had totally recharged my batteries, I was left with Now what? Is this all there is?

There has been little available about retirement planning other than the financial aspect. Coach4Women is spreading the word that there’s a whole life to design when you retire!

Single Women’s Special Concerns

I believe house sitting is an especially safe way for women to solo travel. Do you coach a lot of women who find themselves single – and what are their special concerns about planning how to retire successfully?

Yes, single women do have special concerns. The most obvious is about who to do things with. Particularly for my clients who would like to move to another country, it can look overwhelming when doing it alone.

Traveling alone and safety concerns

Concerns about safety when traveling alone is also what I hear from women who are just starting to travel solo. Women who have been single for a while have already worked out much of the challenges of doing life as a single. Those who are newly divorced or widowed, however, can quickly become overwhelmed when thinking about retiring without a partner.

Single women may have to defer retirement longer because of financial concerns. When they do have a date set for retirement, the specter of isolation can loom large, and if they do not see themselves as someone who makes friends easily, this can be a huge barrier to overcome.

When thinking about where to retire, single women need to think about who their social circle will be. Moving to a different area and starting anew at building a community is more daunting than it is for coupled women.

Travelling in Retirement – The Secret of How to Retire Successfully

I know you’ve recently joined HouseSit Match and that you and your husband parent a very cute dog in a fabulous Southern California 55+ community. Is travel on your horizon – and will you be engaging a house sitter from HouseSit Match? What key things will you be looking for in your ideal sitter (especially since you’ll need someone who is likely retired!)?

Retirement to Discover When and How to Retire
Pauline and Marley
Photo Courtesy of Pauline Field

Yes, we do have travel plans and yes, we hope to engage a house sitter from HouseSit Match. Our ideal sitter will indeed be someone who is retired, or close to it. Our community is a very laid back, safe and quiet environment, so our ideal sitter would be someone who is happy with such a lifestyle – and likes yappy, protective little dogs!


And, Finally…

What’s something most people don’t know about you?

I like to buy as many previously owned things as possible: cars, clothes, accessories. It’s one of the ways that I can help reduce landfills.

Are there any questions you’d wish I’d asked?

Do you think you will ever stop working? And to that I would answer I hope not! Norman Lear, producer and screenwriter, is still working at 98, and like him, as long as I am able to, I intend to keep working.

Thank you, Pauline!


Pauline Field just retired for the third time from the non-profit organization that she founded, 50/50 Leadership.

Her first retirement was from a successful career as a management consultant, including her global management consulting agency, International FieldWorks, Inc. She is widely interviewed about business practices and management skills and is the author of Feisty & Fearless: Nice Girls CAN Be Leaders. She is now the expert on how to retire successfully!

As part of her Coach4Women webinar series, Pauline interviewed Kelly Hayes-Raitt about the many ways she house sat while planning her retirement in Portugal.  Watch here.

Pauline is happy to be a mother and grandmother and lives with her spouse and rescue dog Marley in Seal Beach, California.

Join HouseSit and discover the world of housesitting, please follow these links:

HOUSESITTERS – to find house and petsits all over the world

HOMEOWNERS – to find collaborative house and petsitters for affordable pet and home care

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Kelly Hayes-Raitt

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