Diane Rolston Coaching
  • Home
  • Coaching
  • Services
    • Speaking
  • About Diane
    • Customer Reviews
  • Connect
  • Blog
  • Store

 

The New Way to Build and Maintain Meaningful Friendships as a Busy Woman

4/29/2026

0 Comments

 
Women ask me, "Diane, how do you maintain friendships if you're a busy woman?"
That's what I'm going to talk about today. Not just how to do it, but the new way to build and maintain meaningful friendships as a busy woman.
Picture
This is the last blog of a four-part series all about friends, which was sparked by me being vulnerable and sharing how at my 50th birthday (which is in three and a half years), I want to have 50 girlfriends there. I say girlfriends just because I am craving, wanting more, closer female friendships.
Friendships Don't Just Happen
We all know friendships don't just happen. But what do we actually do to make them happy and healthy and meaningful?
I used to think friendships had to be forged over years and years: high school friends, some sports friends, neighbourhood friends. 
They don't have to be forged over long dinners, big plans, lots of time. That's also because I don't have a lot of time, and I suspect you don't either.
Because of this, I decided, "Well, I guess I'll be friends with who I can be friends with in the time that I have and in the things that are already happening in life."
For quite a while, I've actually built a lot of friendships:
  • Over walks
  • Over quick coffees
  • Even over voice notes with people who I don't get to see locally because they live further away
How We Normally Build Friendships
1. Put it in your calendar.
If you don't schedule it, it doesn't happen.
That's just the reality of life. Looking at my schedule every week, every few weeks, I think: Where can I plug in these walks, and coffee dates? Where can I invite someone I know to an event with me, or drive with me to an event so we can catch up?
2. Reach Out Without a Reason
Just sending messages like:
  • "Hey, I've been thinking about you."
  • "Hey, I thought you might like this."
Every time I do that, it's so well received. Sometimes it's "Oh, you were on my heart, and I prayed for you."
This ability to reach out and even connect it to something you've seen before, like sending an impactful article, funny meme, or something that can be inspirational to the person, shows that you're thinking of them and that you care. 
3. Be the One Who Initiates
If you've met a cool person and you want to be their friend, initiate. I stopped waiting because I was waiting a long time for people to reach out, and it just wasn't happening.
Picture
Most other people are waiting too, and they're wondering why it hasn't happened. If you are the one who initiates and sets up the meeting, the next piece is easier.
4. Make a Plan While in a Plan
While you're at the movies, on the walk, having dinner, having a coffee with someone, on the phone for a chat, make a plan for the next time you're going to be together.
I learned this actually from my chiropractor. After my appointment, as I'm paying, he'll say, "Okay, so how long do you want to give it? Three weeks, four weeks?"
I appreciate that because it goes in my calendar. Otherwise, with practitioners that don't book it in with me, I find months go by, and I'm like, "Oh, right, I need to book in." Then I'm too busy to even just book it.
That's the easiest way to do it: While you're on that coffee date, just say, "Hey, let's look at our calendars. When can we meet again?" That makes it so easy to just keep going without a whole bunch of texts trying to figure out your calendar when it's probably already a month or two later.
5. Change Your Focus
From "I'm just going to know all these people" to "I'm going to be making more meaningful connections."
Then ask yourself: How do I actually do that? How do I make more meaningful connections with people?
Is it one of these?
  • Letting your guard down
  • Sharing more
  • Cheerleading the person
  • Offering support
What is it for you that would help you really gain depth in that friendship, in that relationship?
We could think about even the Five Love Languages. What is the love language of your friend in terms of their friendship language? Is it acts of service? Is it words of affirmation? What is it that they need?
You could even ask:
  • "What makes a good friend to you?"
  • "What do you need in your life right now?"
  • "How can I best support you as your friend?"
That would really give more information for a stronger friendship.
The New Way: Blend Friendships Naturally Into Our Lives
I'm encouraging you to try not just a new way, like shorter coffee dates or going for walks, but what if we changed the way we spent time with others?
What if, instead of it being another task, it just blended naturally into our lives?
Invite a Friend to Do Errands With You
  • Grocery shopping together: Either you meet there, do your grocery shopping, then go to your separate homes, or one picks up the other and then drops them off. When I had young ones, I’d do this on a Sat night with a friend. It was like a night out.  I’d even grab a tea on the way.
  • Other errands together: Waiting in lines for things or running here or there is so much more fun when you have someone with you.
Picture
Help Each Other
I did that with one friend. I shared with her, “When my family goes away, I really want to organize my son's room. It's chaos."
She surprised me by saying, "I could help you with that."
And she did, so I asked, "Well, then what can I help you with?"
I just remembered that I need to reach out to her because I haven't reciprocated yet. I was going to help her with some gardening. Since it's springtime now, it would be a great time for me to support her by spending a few hours with her in the garden. Many hands make little work, and it's much more fun to do these things with someone else.
Invite Someone Over to Your Messy House
How about we even change it from, we need to go out for dinner, using a lot of time and money " to " inviting someone over to our messy house to eat leftovers or grilled cheese sandwiches or something super simple?
I remember when a friend of mine said, "Do you want to just come over? I've got some great leftovers." I gladly accepted. It just felt more personal to be in her everyday life.
What if that was the new way we built meaningful relationships?
I remember being invited over to stop in at someone's house. Coming into her house, I noticed that she hadn't vacuumed in a while, and I was like, "Oh, good. She's not perfect, and her home doesn't have to be perfect. This is just normal, and that's okay."
Better that I get to go over and spend time with her than she freaks out and is like, "My house isn't ready, and I can't have you over."
What if we just made it easier for us to do life together?
We don't have to go on these big plans or adventures (though they are fun). What if we just build meaningful relationships as we live our everyday lives?
Take Action Today
With those thoughts, with this new way of building these deeper, more meaningful relationships as a busy woman, what is one thing that you could invite a friend to do with you?
Look at your calendar. See what's on there. Is there something that you can invite them to be a part of?
Then who is that one person that you could reach out to, even if it's just "I'm thinking of you"? Who is the one person that you would like to either rekindle your friendship or go into a deeper, more meaningful friendship with?
Who could you reach out to? Really, that's the first step: just knowing who, and then figuring out the what.
Given that it's spring right now, you could plant flowers, or depending on the season that you're in (maybe it's winter when you're reading this), there's always something that could be done physically outside, like shovelling a driveway, raking leaves, whatever it may be.
What is something that you could do together?
You don't need more time. You don't need to have it cost a ton of money. You just need a little bit of intention and a little bit of innovation to have it be the new way of meeting, doing life together, and building our friendships at the same time.
And that's something you can start today.
We Weren't Meant to Do Life Alone
If you just found this blog, know that I don't normally talk this much about relationships and friendships. I just felt like this is something that a lot of people have been commenting on and sharing with me, the struggle that they have around friendships. So I'm putting time and energy into this because I know it will have a big impact.
We weren't meant to do life alone. We're meant to be surrounded by other amazing women, other friends, people with whom we can live our lives with.
So reach out to somebody today.
Until next time, stay dynamic!
0 Comments

The Wealth Shift: Why Working Harder Isn’t the Answer to Growing Your Income

4/23/2026

0 Comments

 
There comes a point in business where working harder stops being the answer.
You can be doing all the “right” things. 
  • Showing up consistently. 
  • Saying yes to opportunities. 
  • Working long hours. 
  • Carrying a lot. 
  • Hitting goals.
And yet… your income still doesn’t feel like it matches your effort. If that feels familiar, you’re not alone.
Many high-achieving women reach a stage where the very habits that helped them build momentum become the same habits that keep them stuck.
That is why The Wealth Shift was created.
Picture
Why More Effort Stops Working
So many women have been taught that success comes from pushing harder.
Do more. Be more available. Wear all the hats. Keep proving yourself.
That mindset may help you build something real. But it often does not help you scale.
At some point, more effort creates more exhaustion, more pressure, and more complexity, without creating more wealth.
You may find yourself:
  • Working hard, but your income does not match your effort
  • Saying yes to everything and feeling stretched thin
  • Hitting goals, but not feeling satisfied
  • Wondering why growth still feels heavy
This does not mean you are failing.
It often means your next level requires a different way of operating.
What Successful Women Quietly Experience
Many capable women have built businesses through discipline, resilience, and being willing to do whatever it takes.
They are smart, committed, and dependable.
They are also often doing too much themselves.
Behind the scenes, many are asking:
  • “Why doesn’t this feel better?”
  •  “Why isn’t it easier to grow from here?”
  •  “Why am I still carrying so much?”
These are not signs of weakness. They are signs that growth now requires evolution.
After building multiple businesses, supporting women entrepreneurs around the world, leading conversations through the Dynamic Women® Podcast, and helping business owners scale through Virtual Assistant Made Easy, one truth keeps showing up:
The next level rarely comes from more effort.
It comes from a different way of thinking, leading, and growing because success should feel as good as it looks.
And it should create more time freedom and financial freedom too.
The Shift From Effort to Leadership
Getting to six figures and beyond requires a shift in how you think, lead, and operate.
That means moving from:
  • effort-based income to leveraged income
  • being the hardest worker to becoming the leader
  • reacting to everything to operating with clarity
  • doing it all alone to building support
  • chasing income to creating consistent wealth
This shift can feel uncomfortable at first.
Especially for women who are used to being the capable one. The one who handles it. The one who figures it out.
But staying in that role too long can keep growth heavy.
What Needs to Change
Sometimes the next level is less about what to add and more about what to stop.
  • Stop saying yes to everything.
  • Stop overcomplicating.
  • Stop measuring success by how busy you are.
  • Stop relying only on effort.
The next level often comes from simplifying, strengthening systems, building support, and leading differently.
Picture
It also comes from being in rooms with women who are growing too.
Because who you are surrounded by changes what you believe is possible.
Introducing The Wealth Shift
The Wealth Shift is where things change. 
This is not another “do more” workshop.
It is for high-achieving women who are ready to stop working harder for every dollar and start building sustainable, supported income.
Inside this experience, you’ll discover:
  • What may be keeping you stuck at your current level
  • How to shift from effort-based income to leveraged income
  • What to stop doing so growth feels lighter
  • A more aligned path to six figures and beyond
  • How to grow with more ease, clarity, and support
Most importantly, you’ll leave feeling clearer, lighter, and more in control of your growth.
Who This Is For
This is for you if:
  • You are serious about growing your income
  • You are done with hustle being the only strategy
  • You are ready to lead differently in your business
  • You want both success AND satisfaction
This is NOT for you if:
  • You’re looking for quick hacks or shortcuts
  • You’re not open to changing how you operate
  • You’re not ready to invest time and energy into your next level ​
Join us virtually at The Wealth Shift, happening on April 29th, 9-11AM PT.
And since you’re reading this, I’ll gift you a seat!
Picture
It will be intimate, interactive, and focused on real shifts.
You’ll be surrounded by high-achieving women who value depth, honesty, and meaningful conversations, not surface-level networking.
Because sometimes one room, one conversation, one shift in perspective can change everything.
If you are ready for your next level, this may be exactly the room for you. Make sure to save your spot here.
0 Comments

The Friendship Gap That No One Talks About

4/15/2026

0 Comments

 
There’s a friendship gap that doesn’t get talked about much, but a lot of high achievers feel it. Today, I want to share what that gap really is… and see if any part of it feels familiar to you.
Picture
This is the third in a series all about friendship. The first one is about the 50 friends before I’m 50 challenge that I’m committing to. The second one is about why high-achieving women struggle to maintain friendships. The next one will be about how to build and maintain meaningful friendships. 
The Gap Isn't About Not Having Friends
It's deeper. It's about the depth of those friendships.
There's something I don't think we talk enough about: we can have a really full life but still feel really disconnected. You can know a lot of people and still not feel deeply known, or still feel lonely.
I've had moments where my calendar is full of events with lots of people, my business is moving forward, I have lots of clients, my family is good, and yet something feels a little bit off. It's not that I feel bad or like life is terrible. It's just like something's missing.
When I really looked at it, it wasn't more people I needed. This is not about getting just 50 people to be my friend, because I can just name off 50 people.
It's the deeper connections with the right people. I'm not saying there are wrong people, but the right friendships for me and that I'm the right friend for them, and that we have a deeper connection.
Surface Level vs. Depth
What I’ve noticed is this layer of surface-level friendships and acquaintances.
There are a lot of people in my life. A lot of conversations, interactions, and little touchpoints throughout the day. It can look full from the outside.
But it doesn’t always feel deep.
And it’s not because they can’t go there, or I can’t go there. It’s just that we haven’t crossed that line into something deeper yet.
The Circles of Closeness
I was talking about this inside my Dynamic You program, and one of the women brought up something really interesting.
She said, “I know a lot of people… but I don’t actually want to bring everyone in close.”
Because she’s so warm and friendly, people tend to open up to her really quickly. And she finds herself thinking, “Whoa, whoa… we just met. This isn’t the level I’m trying to be at right now.”
And it led to this conversation around circles of closeness.
Not everyone belongs in the same circle. You might have a small handful of people who are truly close, your inner circle. And then, like rings on a tree, it expands outward. Still meaningful, still valuable… just different levels of depth and access.
The High Achiever Experience
A lot of times, high-achieving women are often the leaders, the ones running things, holding space, teaching, training, being there for others, coaching, advising, consulting, or just being a role model to others. They're often the successful ones in the room, and they just feel like they don't have a place where they can actually just exhale, to be fully themselves, to say what's really going on beneath the surface.
Picture
I realized that I've fallen into that. I've had proximity to a lot of people, but not always closeness.
I was chatting with someone I consider a friend through my church and in the business world. Just sharing openly about this and how it was vulnerable for me to share it. She was like, "Yeah, I thought you knew a lot of people."
I shared, "Yeah, I do, but I don't have a lot of close friends."
She agreed that she's had trouble in certain parts of her life forming those stronger, deeper friendships. She's tried. She's put herself out there, she's reached out, and she just hasn't had the same response.
There's a difference between being around people and feeling truly connected and able to be yourself, where you can let your wall down.
There are the surface-level friendships, the acquaintances, and then the people who really know you.
Often, high-achieving women have wide circles. They know so many people in so many areas of their life, but they don't always get to go deep. That's the gap. That is often a very big gap.
It's not that they lack people or great people who could be fabulous, deeper friends. It's just they're lacking the depth.
Real Life Examples of the Gap
Here’s what it can actually look like in everyday life:
“We should catch up soon.”
And somehow… that turns into months.
“Hey, how are things?”
“Good, good… busy.”
And that’s where it ends.
Those quick check-ins happen in passing, in a hallway, at the mall, in a DM. The moment doesn’t really allow for depth, and if we’re honest, sometimes neither person is ready for the real answer anyway.
And then there are the messages that never get sent.
You think of someone… but don’t reach out.
You mean to send a voice note… but don’t.
You see their message… and don’t get back to it.
Individually, they feel small. But over time, they add up… and keep the relationship sitting at the surface instead of moving deeper.
Picture
I was away recently, and both a neighbour and a friend sent me Happy Easter messages. I remember sitting by the pool, thinking through what I wanted to say back… and then I just never hit send.
When I got home, I felt bad. I apologized and replied, but it made me realize how easily those small moments slip by.
And the same thing happens on social media.
Likes and comments are great. I’ve had moments where I think, “Wow, they care about me. They’re engaging with what I’m sharing.” And that does matter.
But it doesn’t deepen the relationship. It maintains a connection.
Those quick touchpoints, the scroll, the like, the short chat at a networking event… they can fill that space just enough to feel connected.
But not enough to feel truly seen, supported, or known.
When You Can't Let Your Guard Down
There have been so many times I’ve been in programs where I wanted to be vulnerable. Where I needed to process something, or feel frustrated, or talk through not getting the result I was hoping for.
But instead of being supported… I found myself being the one supporting everyone else.
And I realized this isn’t new for me.
Even when I was younger, if I shared something emotional, the other person would often share right back. I remember when my grandfather passed away when I was 16. I was in drama class that day, and during an activity, people were teasing each other. Someone made fun of me, and I started crying.
People didn’t get it. They said, “It’s not a big deal.”
And I said, “My grandfather just died this morning.”
My teacher came to check on me… and then she started sharing about her own loss. She looked sad, and in that moment I thought, okay… I guess I can’t be the one who’s sad right now.
So I shifted.
And I’ve noticed that pattern shows up again and again.
It’s part of why I’ve invested in support, such as counsellors, my naturopath, and my massage therapist. I’ve paid for spaces where I can actually be taken care of… because it hasn’t always felt easy to find that in friendships or even in group programs.
My clients know I can be vulnerable. My friends see that side of me too. But having a space where I can fully let my guard down… that hasn’t always been easy to find.
And maybe you can relate to that too.
Surface Level Only Gets You So Far
Surface-level connections are only going to get you so far. At some point, you start craving something more:
  • Those deeper conversations
  • That real support
  • People who understand you without explaining everything
  • People who understand without the need to say more.
When you have that, you feel seen and heard, and then you can let your guard down.
I hear many of my high-achieving clients say, "Other than you, I don't have anyone else I can lean on." I answer with, "Bring your mess to me so that you can be magnificent out there." 
Full Life, But Empty
We don't want to have a full life but then feel empty. This is what success in life can look like without satisfaction. Friends are one area of life, which is why I'm focusing on this.
I will take responsibility for what I've done or haven't done to gain deeper friendships and close the gap between surface-level friendships and deep friendships.
Where in your life do you have people but not the depth of relationship that you're going for? Who do you actually feel safe being your full self with?
Being Your Full Self
Often, I'm the one holding space or leading. I have to be the responsible one. I have to be the good girl. I have to be the one who sets the bar high. But sometimes, like in school, I can be the straight-A student who gets all our work done, but then I can be the class clown a little bit.
It was surprising when I went away for one of my friend’s 40th birthday to Hawaii for the week. I was able to be silly, goofy, and funny. At one point, she just stared at me. She'd been laughing quite a bit at what I was saying, and she looked at me and said, "Wow, Diane, you're really funny. I haven't seen that side of you."
I felt sad that a friend of mine hasn't seen the funny side of me, because I'm having to be responsible, hold things together or be professional or whatever it may be."
Knowing that you have a safe place to be your full self is so important.
It's About Depth, Not Width
Just remember:
  • More acquaintances won't close the gap. 
  • It's not about the width of the friendship. It's about the depth of the friendship.
  • More proximity doesn't work either. If you see a neighbour friend often in passing, or you're closer in proximity to people because they’re at your work or sitting beside you at your kid’s baseball game, you still have to put in the time and the effort and let your walls down and be that for someone else. Let them have their walls down so that you can connect in that deeper place.
When you have that, it changes everything. You know that at 2 AM you could call somebody to help you. You know if you needed people to do a meal train or to go have fun, you'd have a list of people you could reach out to.
Depth only happens when we choose to create space for it. That is what I'm doing right now, and I guess that's what I've been choosing for the past six months, and will be for the next three and a half years and probably the rest of my life.
What did you relate to? Comment below or email me: [email protected].
Until next time, stay dynamic!
0 Comments

Why High-Achieving Women Struggle to Maintain Friendships

4/8/2026

0 Comments

 
High achievers don't always have many close friends. Some of it is our fault, and some of it is how society sees high achievers.
Picture
If this is something you can relate to, or you're just curious, keep reading. Today I'm talking about why high-achieving women struggle to maintain friendships.
This is the second in a series about friendships. This came about because I started the 50 before 50 challenge, meaning I would love to have 50 close friends before I turn 50. I have three and a half years to make that happen, which is fantastic, because it takes time to make friends.
Reasons why high-achieving women struggle to create and maintain friendships
Reason 1: We’re Busy and Goal-Focused
No surprise here. High achievers often think, “I should reach out,” but don’t. Work and life take over.
We show up consistently for business goals, deadlines, and commitments. Friendships don’t always get the same structure or priority. If a friend truly needs us, we’re there. But the lighter, everyday connection? That’s where things slip.
This isn’t just a stereotype. It comes up often in conversations with high-achieving women. Many feel it, even if it shows up differently.
It’s a familiar pattern:
“I should text her.”
“I should plan something.”
Then the calendar comes out:
“When are we both free?”
“Can I fit this in?”
“Will our schedules ever align?”
Between work, clients, kids, and everything else, it gets pushed to later. And later keeps moving.
We’re wired to prioritize what feels urgent and measurable. Productivity wins. Friendships don’t come with clear metrics or immediate outcomes, so they’re easier to delay.
It can even feel like we have to “earn” downtime. Work first, then maybe fun. So connection gets treated like a luxury instead of a need.
One client realized this when the earliest dinner she could schedule with a friend was three months out. That was the signal that something needed to change.
I can remember someone in an association that I was getting close to as a friend. We did some board stuff together that was really fun. Then she asked me to do some higher-level board stuff, and in her invite, she said, "Hey, this is going to be so great. We could hang out together more." I didn't want to do the board work, but I wanted to hang out with her more. So I replied, "Can I just say no and still hang out with you more?" She was like, "For sure, for sure."
Reason 2: Identity Shifts
As high-achieving women, we grow and change quickly. With each new level comes new roles, responsibilities, and expectations.
Sometimes, the people who understand us best are in similar environments, like business. That’s often where new friendships form.
But growth can also create distance. Not every friendship evolves in the same direction. Priorities shift, time gets tighter, and without intention, connection fades.
It’s rarely dramatic. No big fallout. Just less reaching out, fewer shared moments, and eventually, silence.
Even structured time together can be misleading. You might spend a lot of time with someone through work or volunteering, but once that shared context disappears, so does the connection.
That’s when you realize the friendship depended more on proximity than intention.
Reason 3: The “Later” Trap
High achievers are always working toward the next thing. So we tell ourselves, “I’ll reach out after this launch,” or “when things calm down.”
But things rarely calm down. The next goal replaces the last one, and the pace stays the same.
Short busy seasons are normal. But when “later” keeps getting pushed, it quietly turns into never.
It’s not a time issue as much as a pattern. The same drive that fuels success can also keep friendships on hold.
Reason 4: We Don’t Want to Be a Burden
This one is subtle but powerful.
High achievers are used to being capable, reliable, and self-sufficient. So instead of reaching out, we think:
  • “I don’t want to interrupt.”
  • “They’re probably busy.”
  • ​“I’ll wait until I have more time.”
And we don’t reach out at all.
We handle things on our own, even in moments when we’d normally lean on a friend. Not because we don’t value connection, but because we don’t want to feel like we’re adding to someone else’s load.
How Society Screws Us Over
This is almost the opposite of a lot of the things I've already said, or connected to the things I have already said.
We're told:
  • We are capable, therefore we shouldn't need to reach out to friends to carry a heavy burden or to talk through something.
  • Strong women don't need help. We can do it all ourselves.
We not only have to bear the emotional burden, but maybe a physical one as well when doing things.
Society's Priority Setting for Us
Society tells us: You need that bigger house, that better this, that bigger that, that next level. Our value comes from external things, based on our success, rather than from our satisfaction, which would be the friendships.
They're not valued as highly, though everyone says, "You know, people are the most valuable.” When there's a fire, as long as everyone's okay, that's all that matters.
With higher roles, there's an expectation that you're the first one there, the last one to leave, that you're giving up your evenings, your weekends, that you're always there at the helm. Could you really skip out on an extra meeting at night or somebody asking to meet with you through work and say instead, "I can't, I'm hanging out with my friend"?
It's a little bit frowned upon. Even though people are like, "No, no, family is important, friends are important," saying no to something work-related is very frowned upon.
The Assumption: "They Already Have a Lot of Friends"
Since society says this person's successful, this person's high-achieving, this person knows a lot of people (I touched on this in the last post), they already have a lot of friends. Therefore:
  • We don't need to reach out to them
  • We don't need to see if they want to be included, invited
  • They have a lot of friends, and they don't want to make more friends
Often, high achievers and leaders are the loneliest because we know many people, but we don't have many we can confide in or lean on.
Picture
Many times I've tried to lean on people, and the result was that they leaned right back on me in the same conversation, or they didn't know how to handle it when I became vulnerable, which meant I put the wall back up, pulled back, and acted okay again.
Check on Your Strong Friends
I've said this before: You have to check on your strong friends. You have to check in on the strong women, the successful women in your life, because you never know what kind of demons they're dealing with behind the scenes, or the loneliness & the pressures.
They need not only friends to lean on and share the burden with, but also friends just to have fun, because that's one of the first categories that leaves a high achiever's life.
When we look at the 10 areas, the top three to leave are:
  • Friends
  • Fun and recreation
  • Health (sadly)
We Need to Change
I think as a society, we need to change how things are. Not just having friends in business, but having friends in all areas. As I said in my last blog, I have friends in different categories and different areas: my soccer friends, my church friends, my neighbourhood friends, and my childhood friends.  Those relationships really enrich my life in different ways.
The Truth Moment
We don’t lose friendships by accident or lack them for no reason. The way our lives, businesses, and drives are structured often works against us.
Picture
We can push back against society, but high-achieving women, let's drop the walls a little bit to show a little bit more of the vulnerability, because we're really good at building systems and reaching our goals, except in this category.
Start Making This a Priority
I encourage you to make this a priority if you want to build more friendships or deepen the ones you already have. Prioritize them intentionally so they don't slowly disappear. Instead, they can build up.
You can choose to design this part of your life. Be intentional about your friendships, how they look, and how they fit. When you care about them, you make space for them by giving your time, energy, and attention on purpose.
A good girlfriend time, that's where you get the belly laughs and the care, love, and support.
You can always use this as an opportunity to reach out to a friend, to share this with them, and maybe start a conversation.
Until next time, stay dynamic!
0 Comments

The 50 Friends by 50 Challenge (And What It’s Teaching Me)

4/2/2026

0 Comments

 
I recently published on social media about wanting 50 friends before I turn 50, and I'll be honest, I almost didn't post it. It felt way too vulnerable. 
Picture
In this blog, I'm sharing more about the 50 friends by 50 challenge, why I'm doing it (the vulnerable part), and what it's teaching me.
The Pattern Started Early
Let me start with when I was younger. In high school, I've always been the person who knows a lot of people and is known by a lot of people. I knew classmates, students from sports and clubs and the student council, plus my soccer and rugby friends.
I wasn't around at lunchtime because I was always in a meeting or catching up on something for sports. I had a friend who kept me connected to the group, but I had a lot of acquaintances and teammates, not a ton of super-close friends.
But this was the age of no cell phones and no texting. I'd sit at home waiting for the call to know where people were going, and I wouldn't get it. I'd often sit at home by myself.
I'd get to the lunch table on Monday, and people would talk about a party that had happened. I'd sit there quietly because I wasn't there. People would say, "Why weren't you there, Diane?" Everyone thought everyone else was inviting me. I also had a boyfriend for many years, which took up some of my free time.
The Pattern Continued as an Adult
As an adult, moving out to BC, I started making new friends through Toastmasters, soccer, and rugby. I remember sitting after a Toastmasters event, talking about wanting to hike in North Vancouver, but feeling nervous to do it alone because of bears.
Another lady around my age said, "Oh, I thought you have so many friends you can go with."
I said, "No, I don't."
She was shocked. She said, "I've been wanting to hang out with you, but I just thought you already had a lot of friends."
It was a real eye-opener. I'm either putting that energy out there, or because I know a lot of people, people think I have tons of friends.
I've always had a few super close friends growing up, but one now lives across Canada (because I moved), another in Australia, another across the world and another further away in BC. I have some friends, but again, as an adult, I know many people and many know me. When I was running the Dynamic Women community across eight locations, I met hundreds of women, but they weren't my close friends.
The Birthday Party Dilemma
When it came to my birthday, it felt weird saying, "Hey, do you want to come to my birthday party?" I felt very vulnerable asking. That idea of "Don't you have a ton of friends? You only know me a little bit. Why would you invite me?"
I often had super small birthdays because I felt weird, bad, and uneasy asking people. One year, I didn't really do anything. The following year, I decided to do breakfasts, lunches, and dinners with my Dynamic Women community in different cities. Women came, and it was wonderful. I felt honoured they would want to come.
Since I haven't really been running Dynamic Women® events, I've been thinking, "What's going to happen when I hit my 50th birthday?" I would love for my husband to throw a party for me, but would I have friends to invite?
I've been to other people's 50th birthdays where they rented a place and had all these people there, and it wasn't just people, it was their friends. I thought, "Wow, that would be so cool if I could confidently invite 50 friends to that party."
I'm 46 now, turning 47 in September. It's not like I haven't built closer friends here.
I do have friends at church, soccer, business, in my neighbourhood, and parents of my kids' friends. I just want them to be closer friends.
How I Learned to Be a Better Friend
One lady I met at Dynamic Women® started calling me on Mondays. We'd chat, get closer, and she kept calling every week. I felt so special that she called me.
Picture
A lot of times, when people invite me, call me, message me, or say they're happy to see me, I feel so good. I feel like I've missed out on that kind of feeling, which is very vulnerable and almost embarrassing to admit.
I'm at that stage of life where I've been thinking a lot about friendships and about having more super-close girlfriend friendships. I know people who have had the same group of friends for years, and they all still hang out because they all live near each other.
The Realization
I've built businesses, been married for 16 years, and have kids who are 11 and 14 now. My life is full, just like I'm sure yours is.
Picture
Over time, I started to notice: I've been intentional about growing my business, but not nearly as intentional about growing my friendships.
That friend who became close by calling me every week taught me something. You can intentionally build closer friendships, not just be friends with people by default or hope they get closer.
I don't want to get to 50 and feel like I've let potential good friendships drift or never happen. I want to be surrounded by people at my 50th, not because I want to say, "Look at how many people care about me," but because I want to say, "Look at how many people are important to me, and I'm important to them."
The Surprising Support
I remember someone I'd only met twice found out my son had broken his femur at two and a half years old, and she set up a meal train. I was so surprised. She asked, "Who should I invite to partake?" I said, "I don't know." That seems like something you'd do for a friend, someone you know well.
When I had my babies here and considered a baby shower, I thought, "Who do I invite? I don't even know who I would invite." It's a weird feeling.
The 50 friends by 50 is not for the enjoyment of that party. It's really about the process of getting there and having really rich relationships in my life.
The Vulnerable Post
When I did the post, I thought, "Can I really let this go out there? I should delete it. I don't want it to be public knowledge that I don't have a ton of close friends."
Then the response was amazing. Other people said, "I feel this too. I want that for myself." Some were younger, some older. They wanted to do it as well.
It made me realize how common this is. People are always longing for a sense of belonging.
The most emotional thing was ladies commenting, "I want to be there" (claiming a spot at the party), and people closer to me saying, "Count me in your 50." I had people I don't know well wanting to connect for coffee to get closer. That was really encouraging and exciting.
The Categories
When I came up with this challenge, I went to the notes section on my phone and started listing groups of people:
  • Friends (ones I've had forever)
  • Church friends
  • Neighborhood friends
  • CAPS (Canadian Association of Professional Speakers) friends
  • Soccer friends
  • Business friends
I wrote down the names of people I'm already close to and the names of people I'm intentionally building friendships with. Surprisingly, the list was longer than I expected.
What I'm Learning
Friendships don't maintain themselves. Just because you've known someone for a long time doesn't mean they're in your inner circle. It takes intention and time.
People are more open to connecting than we think. That's really cool.
I've been setting up small, intimate business events that have the potential to build friendships with women who can inspire and challenge me, and vice versa, where we can do life and business together (which is part of why I created Dynamic Women® in the first place).
I've been messaging people: "Hey, do you want to get together for coffee? Do you want to go for a walk?" I have 3.5 years to make this work.
What's Coming Next
In my next blogs, I'll cover:
  1. Why high-achieving women struggle to maintain friendships
  2. The friendship gap no one is talking about
  3. How to build and maintain meaningful friendships as a busy woman
I'll keep you posted on how the 50 friends by 50 goes. It's teaching me a lot and shifting a lot for me.
I've been reaching out to people I haven't talked to in a while, even just to say, "Hey, I was thinking about you." Every time I do it, I think, "Why didn't I do this sooner?"
This isn't about the party with 50 friends. It's about the process and the joy that come with strong friendships and not leaving connection to chance.
Your Turn
That wasn't as vulnerable as I expected (I didn't cry, which is cool), but it is still hard for me to share.
If you can relate, let me know. Send me a message at [email protected]. Share this with a friend or potential friend. Maybe this will start a conversation about wanting to hang out more and do more things together.
Until next time, stay dynamic!
0 Comments

    I'm social, are you?

    View my profile on LinkedIn
    Picture

    Archives

    April 2026
    March 2026
    February 2026
    January 2026
    December 2025
    November 2025
    October 2025
    September 2025
    August 2025
    July 2025
    June 2025
    May 2025
    April 2025
    March 2025
    February 2025
    January 2025
    December 2024
    November 2024
    October 2024
    September 2024
    August 2024
    July 2024
    June 2024
    May 2024
    April 2024
    March 2024
    February 2024
    January 2024
    December 2023
    November 2023
    October 2023
    September 2023
    August 2023
    July 2023
    June 2023
    May 2023
    April 2023
    March 2023
    February 2023
    January 2023
    December 2022
    November 2022
    October 2022
    September 2022
    August 2022
    July 2022
    June 2022
    May 2022
    April 2022
    March 2022
    February 2022
    January 2022
    December 2021
    November 2021
    October 2021
    September 2021
    August 2021
    July 2021
    June 2021
    May 2021
    July 2020
    June 2020
    May 2020
    April 2020
    March 2020
    February 2020
    January 2020
    November 2019
    October 2019
    September 2019
    August 2019
    July 2019
    June 2019
    May 2019
    April 2019
    March 2019
    September 2017
    August 2017
    May 2016
    April 2016
    March 2016
    February 2016
    January 2016
    December 2015
    November 2015
    October 2015
    September 2015
    August 2015
    June 2015
    May 2015
    April 2015
    March 2015
    February 2015
    January 2015
    December 2014
    November 2014
    October 2014
    September 2014
    August 2014
    July 2014
    June 2014
    May 2014
    April 2014
    March 2014
    February 2014
    January 2014
    December 2013
    November 2013
    October 2013

    Categories

    All
    Business
    Business Development
    Coaching
    Entrepreneurship
    Mentoring
    Mindset

    RSS Feed

My services

Coaching
Mastermind
About Diane

Privacy Policy

I respect your right to privacy. Your email or any other information you submit will never be shared.

Coaching Resources

The Coaches  Community

Connect with me

Proudly powered by Weebly
Diane Rolston Copyright@2019
  • Home
  • Coaching
  • Services
    • Speaking
  • About Diane
    • Customer Reviews
  • Connect
  • Blog
  • Store