It gave our Founder and CEO Kara Roberts pause to reflect on her own journey and ask a different question: What can I do today to create a life I’ll look back on with gratitude?
Inspired by Bronnie Ware’s book, Kara found herself reflecting on her own journey through the lens of her Five Regrets of the Dying, not as a list of regrets, but as a reminder of how she wants to live. Five things Kara hopes will help her stay focused on creating a life that feels authentic, meaningful, and uniquely her own.
We hope this sparks a little gem of inspiration for you to pause, reflect, and perhaps make a small shift toward living more fully today.
Inspired by Bronnie Ware’s Five Regrets of the Dying, Kara Roberts personal reflection on each:
I wish that I had let myself be happier. I shake my head when I think about all the stress and anxiety I used to tolerate. I worried about all the little things that really didn’t matter in the long run. Being happy has been a lot easier since getting the right support on my leadership team and becoming a nomad traveling the world. I have so much to be grateful for and find so much joy in exploring new places, cultures and meeting new people with different world views. Getting out of the day to day comfort of my life and shaking things up was a great choice for me. I had a moment when I was riding my bike past the Arena in Verona, Italy with fresh flowers and focaccia in my basket at sunset and thought “No need to romanticize my life.” I’ve built a life and a mindset that brings me joy. I know most people don’t have the opportunity to be a nomad but there are plenty of ways to add more whimsy to your day. Find what lights you up and allow yourself to fully enjoy the moment. Take an afternoon off and head to Pike Place Market to get some flowers and Oh My God peaches at Sosio’s. Head to Discovery Park (literally my favorite place in the world) and walk through the meadows listening to the birds, peer over the bluffs to take in the view of the water and the Olympics, hike down to the beach and try not to belt out Temple of the Dog lyrics in front of the lighthouse. Too niche?
I wish I’d had the courage to live a life true to myself, not the life others expected of me.
This one has been a long journey that I’ve recently made quantum leaps in. There are so many said and perceived expectations put on us. It can be scary to make decisions that go against the norm, can potentially hurt others or change their opinion of you. When I was separating from my husband I made unpopular decisions that friends and family struggled with. I’ve always lived outside of the box and believe that there are 26 letters in the alphabet so it’s never just choosing between A and B. I learned a saying that I still remind myself of 16 years later, “Your opinion of me is none of my business.” There is so much freedom when you realize that you have opinions of others without understanding the full circumstances so of course others will too. You are the only person who knows your heart and your needs and can make the decision that is best for you. Fast forward 16 years now that I am on the other side and the choices I made back then were the best ones for me and my family. It worked out beautifully. Was it easy and graceful? Not at all but I am so glad I had the courage to listen to my inner voice. Something happens when you start trusting your gut and things keep working out. It is a lot less work and a lot more happiness when you listen and act instead of ruminating and worrying.
I wish I hadn’t worked so hard. This one is tough and one I am still processing. I worked so hard for 10+ years building my business. It felt like 24/7 stress because I would literally solve problems in my dreams while I was sleeping. It had a big impact on my physical and mental health. What if I would have had the tools for stress relief and mindset shifts? What if I would have set an hour a day aside for movement and meditation? As a mother of two and a leader of 20+ is that even possible? I’m not sure but I wish I would have known it was a good option to prioritize. One thing I am very proud of was my rule that if my sons walked in, I closed the laptop and gave them my undivided attention as much as possible. As they hit the teen years this time became even more valuable. Now I’m in an amazing season of being out of the day-to-day and have a lot of time for myself. I am grateful to be reaping the rewards of my hard work and I am slowly reversing the effects of chronic stress. If I could go back in time I would tell myself to slow down, breathe and that it is all going to work out.
I wish I’d had the courage to express my feelings. This is a weakness for me that I am deconstructing. I saw a stand up comedian say, “My daughter asked me if I was in therapy as a kid. Therapy? I wasn’t allowed to have feelings. I wasn’t even allowed to be thirsty.” It’s funny because it’s true. I am learning to be brave and ask for what I need and setting boundaries that protect my health and happiness. I have a tendency to make up stories in my head of how people are feeling or why they make the choices that they do. I’m learning to let go of the responsibility of managing someone else’s emotions or reactions to my needs. It’s all about communication and trying to find a place that respects both people’s needs. Brene Brown has helped on this journey. A lightbulb moment for me was her saying niceness is about comfort, pleasing others, and avoiding discomfort, while kindness is rooted in courage, boundaries, and truth.
I wish I had stayed in touch with my friends. I feel like I’ve always been good at this one due to being an Air Force Brat that went to a new school every year until high school. You learn to cherish people that you have a quick connection with. Back then we would stay in touch through letters and occasionally discounted phone calls in the evening if there was something really important to share. As an adult it is harder. We get caught up in our lives and responsibilities. You have to put a lot more effort into it. Being a nomad has helped me. When I’m “home” I’m much more intentional with reaching out to friends to make plans. Sometimes impromptu works the best. Recently I was thinking about old friends and I reached out to see if they wanted to join me at a Seattle Storm game in a hour. They already had tickets! I was able to get a seat right behind them and get caught up. Impromptu hugs are the best!
None of us gets to know exactly how our story will unfold. But we do get to make choices about how we show up for it. These Five Regrets of the Dying are less about looking backward and more about paying attention to how you want to live today.
Here’s a little behind-the-scenes look at life with a Pepper’s personal assistant. A few recent projects that might seem small, but made a real difference in our clients’ lives.
Real-life projects that make real life a little easier.
Doorstops.
Recently, a client had a unique little project for one of our personal assistants. This particular client lives in a timeless older Seattle home. They already had a contractor onsite for the week working on another project, and there was one small thing they wanted to sneak onto the list: doorstops.
Some were missing. Some were worn out. Some were perfectly fine.
The challenge wasn’t necessarily fixing them. It was taking the time to walk through the house, check every door, determine what each one needed, document it all, and communicate the details to the contractor.
The kind of project that’s easy to keep putting off because it takes more time and coordination than it seems like it should.
Thankfully, this homeowner has an incredible Pepper’s personal assistant who toured the home, carefully checked each door, assessed what was needed, took photos, created a detailed list, and handed everything off seamlessly to the contractor.
One small project, off the list.
Color Match.
It’s always amazing how one little project can snowball into a mountain of to-dos.
In this case, it was a new gate needed to keep an eager pup in the yard. The contractor was ready, the specs were sent, but the final paint color “black” was a bit too vague.
If you’ve ever picked out “white” paint, you know there are about 500 million options. “Black” paint offers the same challenge.
Around the estate, black paint had been used as an accent, but the exact color was unknown. Finding a cohesive match could easily become a mountain of to-dos:
Go to the paint store. Select sample swatches. Bring them onsite. Compare them to the existing trim. Narrow it down to the top three matches. Return to the paint store. Wait while three paint samples are made. Return again. Paint a swatch. Review the color in different lights. Cross your fingers. Select the best match. Send the final color selection to the contractor.
Then find out they don’t like that brand of paint, and the process starts all over again.
Who has time for this?
A small “add a gate” task could suddenly snowball into two weekends of paint-store visits.
In swoops Pepper’s personal assistant, with the knowledge and know-how to find the right “black paint” with thoughtful care.
A quick message from the client, and the task was done.
That’s it.
Two weekends lost versus a 30-second text.
Which one would you prefer?
Real-Life Organization.
We’ve all seen those beautiful organization shows. You know the ones where a messy, overstocked pantry transforms over the course of a day into a designer, color-coded, perfectly labeled showpiece.
It’s gorgeous.
But how does real life actually fit into all that color-coded beauty?
Successful organization solutions are the ones that work in the real world and, more importantly, are the ones you can maintain.
They might not always look designer, but when you’re looking for a gift bag for a last-minute birthday party, what’s really going to make your life easier?
Recently, one of our personal assistants did just that, organizing a storage room with real functionality in mind. The goal was simple: save time and create a system that would be easy to follow and maintain.
Clear tubs. Clear labels. Everything is easy to see and easy to find.
It’s not a rainbow, but what it does create is an easy-to-maintain, time-saving system that will work for the long term without creating extra work around color sorting.
Three nagging items, checked off the list. ✔️
What little project has been sitting on your to-do list for way too long? We can help.
At Pepper’s Personal Assistants, we believe the very best personal assistants do more than check things off a list. They create calm in the middle of chaos, anticipate what’s needed, and give clients something incredibly valuable: the space to breathe.
This quarter, we are incredibly proud to recognize Heather Page as our Employee of the Quarter! ⭐
Heather has a remarkable ability to step into a situation, assess what’s needed, and simply make things easier. She brings a calm, flexible, and thoughtful presence to every home she supports.
Recently, Heather’s client was navigating an especially stressful move. After a difficult experience with the movers, Heather proactively offered to come in on her day off to help. She took on the tasks her client was dreading, helped sort through items to sell and dispose of, and brought a sense of calm to an otherwise overwhelming process.
Her client shared:
“I just wanted to send a shout out to the amazing Heather! I was in tears last night after a terrible experience with the movers and Heather proactively suggested she come and help today even though it was her day off! It was such a huge help as she took on the things I was dreading the most without skipping a beat. She has also been a ninja at helping us dispose and sell things from our old home! I have finally been able to relax this evening and Heather has been instrumental in helping our family with this stressful move!”
That is Providing Ease in action!
And it’s not just during the big, stressful moments.
“Heather- I wanted to thank you! Without your work today I would not have enjoyed my weekend away and would have been very stressed today about all the things to set up for the week. It was awesome to come home to a clean home and dinner on the stove and no grocery run to rush out for. Thank you so very much for the gift of time and sanity! We you and Pepper’s!”
Heather doesn’t simply complete the task in front of her. She thinks about what will make the next day easier. She notices what needs to happen before it becomes urgent. She adapts when plans change and she builds trust quickly.
Heather, the trust you’ve built with your clients, the consistency you bring to their homes, and the willingness to go above and beyond are a beautiful reflection of the kind of person and professional you are. You are a wonderful example of our vision: Simplifying Life. Elevating Happiness.
We are so grateful for everything you do for our clients, their families, and the Pepper’s team!
Congratulations, Heather, on being our Employee of the Quarter! 🎉⭐
A 5-minute reset at home is a quick routine designed to restore order and reduce mental clutter without feeling overwhelming. Instead of trying to clean the entire house, you focus on a few high-impact tasks that make your home feel calmer and more functional.
For busy professionals, a 5-minute reset can help you transition between work and home, start the day with intention, or prepare for a more relaxing evening.
Here are a few 5-minute reset ideas:
Morning Reset (Before Work)
Make the bed.
Open blinds and let in natural light.
Load any dishes into the dishwasher.
Clear kitchen counters.
Start one load of laundry.
Midday Reset (Work-from-Home)
Put away anything that’s out of place.
Wipe down your desk.
Refill your water bottle.
Empty the trash if it’s full.
Do a quick sweep of the main living area.
Evening Reset
Load and run the dishwasher.
Wipe kitchen counters and dining table.
Fold blankets and fluff pillows.
Sort the day’s mail.
Set out anything you’ll need tomorrow (gym bag, laptop, lunches, backpacks).
Entryway Reset
Put shoes in their designated spot.
Hang coats and bags.
Toss junk mail.
Return keys to their hook or tray.
Straighten the entry rug.
Family Reset
Set a timer for five minutes and have everyone participate:
Put away toys.
Gather dishes.
Fold throw blankets.
Return items to their rooms.
Empty small trash bins.
Why it works
A five-minute reset isn’t about deep cleaning, it’s about maintaining momentum. Small, consistent habits prevent clutter from becoming overwhelming and create a home that feels easier to manage.
Taking just five minutes to reset one area of your home can reduce stress, create a sense of calm, and make tomorrow a little easier. If you need extra support, Pepper’s is here to help. Book a Discovery Call to learn more.
Connecting with Yourself: Reclaiming Happiness and Self-Care
When was the last time you asked yourself a simple question: What makes me happy?
Not what needs to get done. Not what’s next on the calendar. Not who needs something from you. Just…what fills your cup?
It’s a surprisingly difficult question to answer when life feels full. Between careers, families, pets, homes, aging parents, and the endless stream of emails, appointments, and errands, it’s easy to lose sight of yourself. We become experts at taking care of everyone else while quietly putting our own needs on hold.
The Quest for Time and Room to Breathe
We see this all the time. So many of the people who reach out to Pepper’s aren’t looking for luxury or convenience. They’re looking for time and room to breathe. They’re looking for the version of themselves that had time to go for a walk, bake bread on a Sunday afternoon, read a book before bed, or simply sit down without mentally running through tomorrow’s to-do list.
The truth is, happiness isn’t always found in grand adventures or life-changing moments. More often, it’s found in having the space to enjoy the little things that make you feel like yourself.
For many people, self-care begins when they no longer have to keep every detail in their head.
Here are three simple ways to create more space for yourself:
1. Stop trying to remember everything. Write it down, use a shared family calendar, or create recurring reminders for routine tasks. Freeing your mind from constantly remembering what’s next can reduce stress and improve focus.
2. Decide what only you can do and delegate the rest. Many household tasks don’t require your personal attention. Whether it’s grocery shopping, laundry, organizing, meal prep, or coordinating vendors, ask yourself: Does this actually need to be done by me? Delegate, Delegate, Delegate!
3. Protect time for what restores you. Instead of waiting until everything is finished, schedule time for yourself first. Read a book, take a walk, work in the garden, enjoy dinner with friends, or simply spend an evening without rushing to the next task. Rest isn’t a reward, it’s part of living well.
At Pepper’s Personal Assistants, these are conversations the team has every day. Clients often reach out looking for help managing their homes, but what they discover is that reducing the mental load creates space for something even more valuable: more energy, more presence, and more enjoyment in everyday life.
Every personal assistant and household manager on the Pepper’s team approaches their work differently, but they all share one goal, to make life feel a little lighter by thoughtfully handling the details behind the scenes.
Their impact is best described by the people they support.
Exceptional Home Management
“Bernice is simply amazing—I just can’t say enough good things about her. She excels at physical tasks and knows my habits so well that she can anticipate my needs without me even saying anything. As a house manager, she’s exceptional; she takes care of all those little things that I wouldn’t even think of. Over time, we’ve developed a wonderful rhythm, and it’s such a relief to have someone who just knows what needs to be done and does it effortlessly.” – J.H.
Support That Makes a Difference
“Having Missa as a PA has taken me from daily treading water to swimming to the shore. I’ve gone from never quite keeping up with things to actually having extra energy to do more. She has been a tremendous help, reducing my stress and allowing me to rest and recover. The support I receive is perfect; Missa is a 5 out of 5 in meeting all my needs. I’ve already recommended Pepper’s to a few friends because having extra help makes all the difference.” – Kathy M.
A True Game-Changer
“Having Mary as my personal assistant has been a game-changer. I don’t have to think about laundry or the cat litter—she handles all those daily tasks I’d rather not do. She’s proactive, assertive in all the right ways, and totally in control of every detail. I’d rate her a 5 out of 5, no question!” – Brian T.
There will probably never be a season when life naturally slows down. Work evolves, families grow, responsibilities shift, and new commitments take their place.
Instead of waiting for life to become less busy, consider where you can create a little more margin.
Whether that’s building better household systems, asking for help, or simply letting go of the idea that you have to do everything yourself, creating space isn’t about doing less—it’s about making room for what matters most. Happiness isn’t found in checking off one more task. It’s found in having the time and energy to enjoy the life you’ve worked so hard to build.
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