Welcome to her comeback. I'm so glad you're back
with me. This is where 50 isn't your finish line.
It is your starting point. The starting point
of everything you want your life to be. The person
that you are meant to be. I'm your host, Michelle
Thompson, and we are proving that your best chapter
may just be the one you haven't written yet.
We'll continue each episode featuring honest
conversation with women who have stopped going
at it alone and have found their way to fulfillment,
joy, and purpose in their second act. You'll
hear about their struggles, their breakthroughs,
and the practical steps that they took to create
lives that they actually love. This podcast will
show you how other women have made their comeback
and how you can too. Welcome back. Good day,
everyone. Welcome to her comeback. I am so happy
to have today Cheryl Dillon all the way from
San Diego, California. Welcome, Cheryl. Thank
you. I'm so happy to be here, Michelle. Oh, it's
so wonderful to have you. We have a few things
I was going to ask you, but just could you get
us started? Just maybe just some general things
about yourself you'd like to share before we
get going. Oh, sure. Well, I am originally from
New Jersey, born and raised and lived there for
the first 40 something years of my life. And
then moved to Chicago and lived there for five
years. And it was right when the Cubs won the
World Series. So I'm a huge Cubs fan. My dog's
name is Wrigley. Like we're really, you know,
all in with the Cubs. It was really fun to be
there. The winters were a little bit too much
for me. So we've been out in California for about
seven and a half. half years and I feel like
I couldn't go any farther west at this point
you know unless maybe Hawaii but just you know
I will never lose my Jersey -ness. The good news
is when I lived in Chicago I got a little friendliness
to me so I lost a little of my edge and and then
now out in California I think maybe have gotten
a little bit more laid -back although like a
smidge. Very good, very good. So you've spent
your time these days with the community that
you've established for women in midlife. Tell
us a little bit about that. Yeah, thanks for
asking. I started a company called Thunderful
Experiences last year and it's the umbrella.
I had gone back to school, you know, after all
my life coaching skills and my, you know, psychology
background and all the work that I had been doing
up until this point. I knew that I wanted to
do something a little bit more joyful. I had
an idea of what I wanted to start but I needed
some additional skills so I went back to school
last year and I got a certificate in event planning
and then I put put that in with with everything
else and I started a company called Thunderful
Experiences and it's It's got different facets
to it. So I write a free newsletter called the
uplift. It goes out every Thursday and it's just
a little bit, you know, stories from my own life,
some challenges that I faced or I'm facing. It's
meant to be uplifting, help other people see
that they're not alone if they're experiencing
any of these same things. And then I give them
some tips on how I've addressed it or I'm working
to address it so that hopefully if they resonate.
they'll be able to use some of those things as
well to help themselves. Another facet of the
company is a membership community. It's local
and it's called Connected Hearts and the purpose
is to bring women in their 50s and 60s together
face -to -face for personal growth, for some
conversation that goes deeper than small talk,
friendship building and also we have a lot of
fun and I've really noticed Throughout the pandemic
where we were also isolated, social media were
online all the time. I really was craving in
-person connection. So this community is new.
We're going to have our second official gathering
tomorrow night and it's growing and we're just,
we're really enjoying what we're doing. So it's
basically the community I always wanted, but
could never find. So I decided to build it. And
then the third aspect of the company is private
coaching. In the future, I'm looking to also
do some one -off events, maybe couples or some
retreats or some conferences. But right now,
just enjoying day by day how things are growing
and evolving. Oh, that's wonderful. I love that.
You describe a midlife pivot and you say that
midlife is not a crisis but a powerful turning
point. Can you walk us through a moment when
you realized you wanted to intentionally design
this next chapter rather than just let things
happen? What was the catalyst? Yeah, there's
a lot of things. It wasn't one. one thing. It
was a whole bunch of things that were sort of
happening within a period of time. One of the
things was moving to California because I moved
here in my late 40s. I work from home. I don't
have children, not human children. Mine have
four legs. And so I really felt like I had no
built -in community. All of my deepest friendships
were on the East Coast. I did make some good
friends in the Midwest, but here it was essentially
starting from scratch. Also, you know, The pandemic
happened very soon after we settled into our
home. So right when we were, my husband and I
were ready to go out and meet people, we couldn't.
And I feel like that pandemic really actually
took a lot of motivation out of me because once
it lifted and you could go back out, I was very
complacent. It was, you know, I'd rather be home
in my sweatpants, you know, versus like getting
up and out and putting yourself. out there. I
have lost some of those skills I think and the
motivation. So even though I was looking to meet
friends and build community like physically and
physiologically I just couldn't get myself up
and out so easily. So I was feeling pretty isolated.
My father passed away when he was 58 and this
year I'm 56. So I'm starting to sort of have
these jolts like First of all, how did you get
to be this age? You know what just happened and
also Reflecting on the fact that you know, we're
all kind of marching towards the same destination
and It really was just like looking in a mirror
if I want to make some changes and if I want
my life to be different Now's the time to do
it because if not now then when I had visited
a close relative who actually lives in Florida
and I realized also a pattern. My grandmother,
when she was getting older in life, you know,
I had always seen her as a little girl, as this
very outgoing, social, you know, big personality,
friendly woman. And then as she got older, she
was just inside all the time, sitting in her
chair, watching TV. Again, I don't know if she
was depressed or what was, I know she had some
arthritis and some health issues, but. I just
saw a really big change from what I remember
of her when I was young to what I was seeing
as she was getting on in life. And then I went
to see another relative. Last year and I started
noticing that same pattern and I'm afraid because
I don't want that for my own life So again, it
was another jolt like you better do something
because if you keep doing what you're doing You're
gonna keep getting what you're getting and it
wasn't aligned with what I wanted and so I realized
that I was waiting for life to feel differently
instead of me designing it for how I wanted it
to be and sort of felt like It's the first time
where I realized that I have enough self -awareness
and you know emotional intelligence and perspective
to Just do what I want to do now again with all
these other things happening. It just felt like
the right time to make a big change That's terrific
and I love what you describe that connection
and the power of connection because you know
needing to feel that and just critical to good
mental health or good health in general being
able to feel those connections how important
that is. So from doing the right things to doing
your thing, you spent decades being responsible
and showing up for others. And I think that's
so common that so many women over 50 can relate
to. How did you navigate that emotional shift
from external validation to that internal fulfillment?
And what advice would you give to women who have
that guilt about prioritizing themselves? That's
a great question. And by the way, I'm still a
work in progress shifting that external validation
thing. It seems to be ingrained, you know, from
a young age and a lot of other women that I speak
with, they say the same thing. You know, you
just grow up with these expectations and, you
know, to be the good girl or the good wife or
the good daughter or, you know, dot, dot, dot.
You know, many of us are working full time. We're
taking care of the home. A lot of the women in
my group. have children so that you know they
raise the kid like they're doing so much and
a lot of it of course they love the kids of course
they love their spouse but a lot of it is just
these expectations that they feel and this obligation
to just be the responsible woman you know to
get it all done they're the emotional support
for all of these people and I think you know
this is the time now you know for myself I explained
what my motivation is to make that big change.
It doesn't mean I don't love the things I'm doing.
It doesn't mean I don't want to be there for
everyone or want to make sure my house is running
or whatever else. But it also means that I am
deliberately carving out time for myself and
to focus on my own needs and really focus on
What are the things that are meaningful? And
realizing that, again, if you don't make a conscious
decision to seek that out and design it. no one's
going to just realize that and hand it to you.
So it is really your responsibility. A lot of
the other women who are in my group and my friends,
they say, now the children are adults. You know,
a lot of them are empty nesters or the kids,
some of them, the kids are boomeranged back home,
but still the children are adults and they feel
like now it's my time. And so even though their
identity has been wrapped up into being the mom
or, you know, this primary you know caregiver
they're starting to wake up a little bit and
and see I don't I won't trade all those things
I did but now is time where I can finally like
take a breath and decide you know what I want
and just start prioritizing myself so I think
that in terms of doing all the right things for
many of us it's natural and we don't question
it. We measure up to our parents' expectations
or our teachers or society, whatever we think
we're supposed to be doing. And not everyone
gets this awareness, but the ones who do realize
whose beliefs were those or whose expectations
were those. And with the time I have left, I
deserve some time for me. I deserve to do the
things I love. I deserve to be happy and are
now making the space to create lives like that.
Absolutely, that's that's beautiful. I love that.
And it's so true. You mentioned, you know, your
father passing an early age and, you know, none
of us know, you know, nobody's guaranteed, you
know, how long a life we get to be here and just
to know and be able to take what we have today
and do the very most with it, make the very best
of it. It's the way to go. Wonderful. There was
something you mentioned that you noticed kind
of a connection gap, that the events and communities,
a lot of them seem designed for the under 50
crowd. What do you think older women need that's
fundamentally different from maybe the younger
demographics? And why is finding that authentic
connection so much harder at this age? Do you
think? Yeah, great question. I actually feel
like all people, women and men need connection.
And my perception is that society idolizes the
youth and that when you get to be a certain age,
you know, like men get distinguished when they're
older, but women just get old or discarded or
if beauty was, you know, what made them important.
as that starts to fade visually, because they're
still beautiful, but their appearance changes
getting older, that society doesn't seem to acknowledge
or respect or celebrate that. So when I say about
under 50, it's really like under 30, but it just
sort of feels like women at our age need to remember
that yes, things might be changing when you look
in the mirror. You don't look to say, I look
in the mirror and I'm like, what just happened?
Where did this wrinkle come from or what's going
on here? But that again, because we believe society
only cares about us if we are young or beautiful
or thin, that it's really important that as women
are getting older, they don't buy into that.
And so I think what's missing in midlife spaces
There's a few things. One is emotional safety
and I can speak from my own experience. I never
really had a close group of women friends because
they all just became very clicky or competitive.
Somebody was always gossiped about or like undermined
and so for me throughout life I always saw groups
of women as scary and because I had gotten hurt
or I felt left out or you know it was the target
of something and so throughout many years I might
be lucky and have a close woman friend but not
a group of them at the same time and fortunately
my husband is my best friend so I you know Enjoy
spending time with him, but there are just certain
things you don't want to be talking about With
your spouse or there are just certain things
that only other women would understand or appreciate
so this year I made an intentional decision that
I wanted to make a group of women friends even
though I'm scared of them and That I was going
because I'm building it now that I'm doing it
the safe way, the way that I would want supportive
and women who really genuinely care about each
other. So I think having the safety, if there's
other women who have experienced what I have,
and I hear these same kinds of stories about
groups of women and drama and like all these
things that happen that maybe there's some apprehension,
you know. not to connect with somebody because
you don't trust them and you feel like whatever
happened in your life, your disappointments or
your hurts are going to happen again. So you
kind of stay away from that. Also, I think there's
more and more women who want to talk about things
that are deep, not just, you know, what car you're
driving or or your clothes or you know how much
money you have or they want to just have some
deep and meaningful conversations but they don't
need therapy they just connect on a deeper level
and and i'm in that bucket too i just i love
to have meaningful conversations with people
to me that's more of a bond than these, you know,
friendly acquaintances. So and then I also think
that even though many women want to connect,
they actually don't know how. And, you know,
we don't learn it in school. And not everyone
is a natural extrovert. And so people need to
feel like they're in an environment where they
will be asked a question and they will have time
to answer without someone cutting them off or,
you know, they just have to feel comfortable,
safe, included. And I think that those are some
things that have prevented some connection. And
then as your children get older, you don't have
built in ways to meet other people. Maybe as
your children were younger, you had friendships
with the parents sitting in the bleachers at
the soccer game or, you know, in the little league
or something, or the scouts. And as the kids
get older, You know the only thing that maybe
connected you with these other people was the
shared children so there isn't anything to keep
you connected and also You know some people are
widowed or some people are divorced or some people
especially in my area are retiring and moving
here so again, they're starting with no knowing
no one and Having to start all over again without
these easy built -in ways to meet people preventing
connection and we're all so busy and you know
social media it's amazing how time evaporates
when you're just scrolling or when you're watching
the news and you just feel so depressed about
what you're reading that you just don't want
to go out so I really feel like there are many
many things creating the connection gap and even
though we all as humans need connection It's
like an uphill climb and we really have to make
some bold moves to to start to create that, you
know. Do you find that women in your group kind
of embrace some of this vulnerability that you're
talking about? Or do you think some are still
a little resistant to that? What do you see there?
Yeah, it's a great question. You know, fortunately.
I lead so. If I share, I share a lot of vulnerable
things in my newsletters, in my group, just in
life when I'm out talking to people. And you
obviously have to read the room. You know, it's
not like you're going to meet somebody and talk
to them about your childhood trauma or like your
cholesterol numbers or, you know, that you have
some health thing. You kind of have to know who
you're talking with and what kind of situation
you're in. But I do feel, you know, if I share
something first, I'm leading by example and I'm
showing everyone that I'm courageous and that
this is what I want and this is who I am anyway
and I'm willing to be myself. Then they can take
the lead because they see that it's okay. They
have permission to be vulnerable. You know, in
my community we have some guidelines. It's called
the Connected Hearts Promise because Connected
Hearts is the name of my group. We just have
some guidelines where what we talk about in this
space is kept in confidence or we don't interrupt
each other. If someone has the floor, they have
the time to share. Sometimes people need time
to process before they start talking. They need
a little more introspection. Sometimes someone
else will jump right in then and fill that gap.
but our guidelines really prevent that. There's
different ways that we interact with each other
that shows a lot of mutual respect and that we're
all wanting to be in there for the same reasons
and we're willing to kind of follow these rules
because it preserves the integrity of the space.
And so there are people who flat out don't resonate
with this at all. they don't come in which is
a good thing right because this isn't for everyone
and if we had somebody come in where everyone
else is sharing and someone isn't it does create
some Safety concerns emotional safety, you know
people feel comfortable when everyone sharing
and certainly We don't force anyone to say anything.
They don't want if someone doesn't feel comfortable
They just pass and there's no judgment but I
just feel like there are some unspoken and spoken
rules that help people to feel more comfortable
and wanting to share. And I feel like because
there aren't a lot of spaces in life where it's
acceptable for them to share in this way, like
you're not going to go into your workplace. You
know, it's like... My experience working in a
corporate environment is you're really not supposed
to be very emotional. It shows weakness or you're
not supposed to bring your personal stuff into
the office. So my point is, I think at least
the women that I am connecting with are really
wanting this because it doesn't exist anywhere
else where they feel like it's welcome and it
makes them feel less alone. Truly a safe space.
Yeah, you're also running mediation practice,
helping people through their divorce transitions
and the wonderful experiences. So how do you
see the parallel between helping people exit
one chapter of their life and then embracing
a new one? Yeah, I've worked with my husband
and partner in our mediation and coaching practice
for. Gosh, 17 years now? So a long time. I myself
was previously divorced and used mediation. My
husband's parents had a pretty terrible divorce
when he was a kid, and so he knows what not to
do, right? But we've been working together for
all these years, helping people, you know, respectfully.
end their marriages, you know, preserving their
bank accounts and preserving their relationship
with their children. But it's a really painful
time in life, a divorce. It is a major life transition.
And in my community now, working with women in
midlife, it's also a life transition, right,
where a lot of people, their identities are changing.
If they're an empty nester, or again, if they're
divorcing, or if they're a widow, or if they're
retiring, just, it's an identity loss. when you
look in the mirror and you're like, how on earth,
you know, what just happened? You know? I'm sitting
here, who am I? Yes, these are kind of lots of
deaths. You know, you have to sort of grieve
the loss of these things, these parts of you.
There's some similarities in divorce and what
I'm doing. These are all major life transitions
and there are different phases people go through
when they're healing from it. And I help them
really build resilience so that they can kind
of reflect on what's happening, accept it however
they can, heal from it if that's what's needed,
and then be optimistic as they carve out what
they want next, you know, for their next chapter.
I think that a lot of people, they fear the unknown
more than the pain they know now, and it's horrifying.
It's like a new frontier, you know. I don't know
what to do now, I'm lost. And I feel like an
identity loss, it's harder a lot of times than
a logistical change. It was a big change to physically
move from New Jersey to Chicago or Chicago to
here. But an identity loss is something, it's
not tangible. You don't see it and it's more
difficult. It's like a silent thing, but it's
still pretty significant. And I also feel like...
because divorce there's so much stigma although
maybe maybe not so much anymore but it depends
the stigma of it there's a lot of embarrassment
or you're ashamed or you don't want to broadcast
it you feel like something's wrong with you or
that you're a failure same thing in midlife some
of the things we're talking about it's like you're
not going to talk to your husband about how like
there's a chin hair like you're just not going
to talk to your husband about what's going on
for your body or how you can't sleep through
the night anymore or a lot of us feel very isolated
and alone and I feel like in order to heal and
grow and move forward that requires support and
it's like there's so many similarities between
the mediation and the midlife women and it's
that resilience it's not about just powering
through get over it it's really about slowing
things down listening to yourself choosing differently
next time in ways that really align with your
values and your integrity. So beautiful. What
would you say is maybe a universal truth that
you've learned about resilience during these
transitions? Anything that comes to mind? Yes,
I've learned that the key to resilience is being
your own best friend. And you know, if you think
about it a lot of times, especially in a divorce
situation, you... Feel like your spouse you lost
your best friend, right? You lost the person
you're confident or someone who was always there
for you or that had your back maybe the divorce
is because that that person didn't have your
back but but but during the marriage you get
married and you feel like the process of getting
married means you have someone looking out for
you or who's there with you through through the
good times the bad times who's got your back
and And then when you're making a major change
you you don't have that person anymore. But who
do you have to help you? You. And this is really
a time to start thinking about being your own
best friend is trusting yourself, really loving
yourself, taking care of yourself and treating
yourself the way that you expect everybody else
to treat you. Because if you aren't kind to yourself
and if you don't have self -compassion, You're
not going to attract people in situations into
your life that that mirror that back And so when
you're going through these major life transitions,
and you need resilience it comes from inside
It's it's from you certainly there are lots of
places to get support therapists, self -help
books, there's support groups. Same thing for
midlife. There are support groups. You can go
to therapy. And all of those are wonderful ways.
But even those things are helping you reconnect
with yourself. And if you have a great relationship
with yourself and you love and care for yourself,
the choices you make and the way you look at
life are going to be in alignment with that and
you're going to have happiness. You know, because
it only they would say, right, it comes from
within. Absolutely. So important. That's that's
right. Well, I have really enjoyed our conversation
here, and I am just really thankful that we were
able to connect and you're able to join me today
as we wrap up. What else would you like our audience
to know about your community or anything, anything
that you're promoting? What else would you like
for everyone to know about you? Yeah, thank you
for asking me. I would say a newsletter is available
to women who live anywhere. So if you want a
weekly dose of inspiration and reflection and
just to know that you're not alone, you know,
to have a weekly little bit of joy, so please...
subscribe to my newsletter which is called The
Uplift and you can do that directly on my website.
It is wonderfulexperiences .com slash get dash
v dash uplift so that's one way and if anyone
lives in coastal north county san diego and resonates
with the things that I've spoken about. I hope
you'll check out my group, Connected Hearts,
and there's a membership tab on the website as
well with more information about coming as a
guest. Oh, that's wonderful. Well, thank you
for the work that you're doing. I absolutely
love the community that you're building and the
connection that you're making with women and
just being able to be that safe place where women
can come and share and be open and vulnerable
and make true genuine. have true authentic relationships.
That's just awesome. I love that. It's a great
thing. Thank you. So thank you. And I wish you
all the best. Continue success as you build your
community and your business there in San Diego.
Thank you. Thank you, Michelle. Thank you so
much for spending time with me today. I am truly
grateful that you chose to listen in and I hope
that this conversation sparked something meaningful
for you. Please take a moment to subscribe, leave
a review. It helps other women to find us who
need to hear these stories too. And if you know
someone who is ready for their own comeback,
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The question isn't, can I transform my life?
The question is, are you ready? Let's go. Said
all the right things just to belong Smiles so
sweet