Words of wisdom from my mom on her 60th birthday
The Sunday Series on a Monday = free! letter!! today!!!
Hihi, from upstate New York!
This Thursday found me back at seemingly my favorite place this summer: the airport. But this time, it was to go home to Buffalo (I grew up an hour north of The City of Good Neighbors in a rural town on Lake Ontario) to celebrate both a wedding and my mom’s 60th birthday.
The wedding festivities took place Saturday and were such a testament to how life-affirming our oldest relationships can be…it’s so rare that I get to spend quality time with all my high school friends, but this wedding was a gathering that brought together our crew dating back decades. What a powerful reminder that the people who’ve known us the longest will always feel like home.
In the spirit of trying to be present for both that wedding on Lake Canandaigua and being amongst family who’ve come to town this week to spend time with my mom, I wasn’t able to get the letter out on Sunday and for the first time ever (!!) cut myself some slack to send on Monday instead. But today is no ordinary Monday—it’s my momma’s 60th birthday.
So, I’m switching up today’s format to be a Q&A with the birthday girl herself. We had a chance to sit down and talk about some of the standout moments from her last 60 years, advice she’d give her younger self, and what she wants to bring into this new decade.
Since much of this conversation wound up being career-driven, some helpful context is that my mom is a Human Resources professional with several career coaching certifications in addition to her MBA. Over the ten years I’ve been working (today actually also marks my seven-year anniversary at SmartFlyer!), I’ve gone to her countless times for guidance, even sending many friends to her for coaching. If you’re looking for a career coach and want to be connected with her, email me, and I’d be happy to facilitate an intro! xKD
But before we dive into my Q&A with my mom, I wanted to share some gift ideas! It can be overwhelming to nail a birthday gift for someone you love dearly, but I find sentimentality is always a good guiding light. Here are some of my faves to consider.
PhotoPanda | This was our big gift for mom this year…a seamless way to digitize thousands of our family photos! You just pick a box size (we did the large box), they send it to you, then you organize and send in your photos for them to digitize. Super excited about this find!
Today’s Special Recipe Book | We got this one for my mom to start handwriting her own recipes in it for us!
New York Times Custom Birthday Book | I looooove this one so much but you need to order at least 10 days in advance of when you need it!
Framebridge Burlwood Gallery Frame | A great one for framing a sentimental letter or document.
14k Gold Itty Bitty Letters Bracelet | Would be so cute to get a family member’s name on this bracelet.
4.5mm Round Cut Gold Rivière Necklace | Because who wouldn’t be happy to have a tennis bracelet?
Classic Monogram Waffle Pouch or Custom Boxers | Love supporting small, female-founded brands and Abbode is one of the best when it comes to embroidery!
Anya Hindmarch Vanity Kit | Dream dopp kit...you can personalize, too.
La DoubleJ Feather Slippers | A great gift for the woman who has everything.
HigherDose Infrared Sauna Blanket | This one was on my Mother’s Day Gift Guide and super popular…have friends who own it and are super happy!
💸 Aaaaaand as a disclaimer, this shopping section—as always—includes affiliate links. These little babes help me continually reinvest in making The Sunday Series better. I make a small commission when readers click and shop through my links at no additional cost to you—so if you found something through a link I sourced, please do consider purchasing through that link so I’m credited! Speaking of, I’ve been using the ShopMy platform for several months and love it. Want to start making commission on the links YOU share? Sign up with my referral link for a 10% bonus on your fist six months of linking.
Meet Jill Whalen Helms
If you’ve ever wondered where I get my drive, my love of a good to-do list, or propensity for thinking I can fit a figurative ten pounds in a five-pound bag, let me introduce you to my mom: Jill Whalen Helms. She’s spent over 15 years leading high-impact HR teams, coaching executives, and helping companies build cultures where people actually want to show up. Her current title—Strategic HR Business Partner at Moog Aircraft—only scratches the surface of what she does best: connecting with people, listening deeply, and guiding them toward roles that allow them to shine. Today, this Leo turns 60, and while her résumé is full of impressive credentials (MBA, CPCC, etc. etc.), my favorite title she holds is “Mom.”
Kayla Douglas: What is a little ritual or habit you swear by?
Jill Helms: When I can do it, the best way to start my day is to come downstairs, start the coffee, and sit in that chair by the garden with my journal. I listen to a meditation. I write in my journal a little bit, go into the house, do a little yoga, and go get ready for work. If I could do that every morning, that is my absolute favorite ritual.
KD: What's your earliest memory of what you wanted to be when you grew up, and how did that evolve over time?
JH: I mean, that took me a long time to figure out. I didn't ever have a “Oh I'm gonna be a this or that” moment. I didn't have a high school guidance counselor, who said, “Oh, why don't you go to college,” and certainly nobody in our family encouraged that. We never talked about college.
The only thing I was ever told I could be was a secretary, so that's why I went to a secretarial school. I lived with my sister Linda in Virginia, and the secretarial school was like a 40-minute drive over to Maryland. I had a part-time job while I was in secretarial school, working at a retail store, which is why I ended up shifting to a retail management program.
That was my next idea. Because you don't know something until you get exposed, I realized, “Oh, I could be the store manager of a retail store.” It's the only thing I could see. But after my first semester of retail management, I switched to business administration. I was still working like 25 hours a week. I had a job the whole time I was getting that two-year degree.
Eventually, I worked this hotel gig and did some admin work. There were so many bumps along the way, like when I was eight months pregnant with Brooke and my company closed. At one point, I ran a daycare at home for a while, then I got a job as a Business Manager at the Kenan Center. And while I was working at the Kenan Center, I started doing a little HR stuff. So in 2001, I went back to college to get a bachelor’s degree and was finally on my way.
KD: What's the best decision you made in your 20s?
JH: The best decision I made in my 20s was having you two. And I feel really lucky because as soon as I stopped birth control, I was pregnant. I had you at twenty-eight and Brooke a few weeks before I turned thirty. Being a mom is the best thing that ever happened to me.
KD: Alright, so your best decision was having us. Your worst?
JH: I mean, I'm sure I did a lot of stupid things. But I don't believe in, “Oh, that was a terrible decision.” Everything leads to something else. Even things that were hard or weren't good, I just feel like this is the path.
KD: Okay, so what's something you wish you knew at 30 that you don't know?
JH: I would have said go back to school sooner because that's how I was able to start saving money. But my solution early on was to have two jobs. At some point—and I can't exactly say when that dawned on me— that going back to college was better than working two jobs, because I cannot remember how many times in my life people said to me, “Well, if you just had a bachelor's degree...” You just did not have job opportunities without a bachelor's degree. It was a differentiator.
KD: What was the biggest shift between your 30s and your 40s?
JH: I got my Bachelor's degree in my 30s, and when I was 44, I went back to get my MBA, which I finished when I was 46. That opened a lot of doors for me.
I mean, don’t forget, at 38 years old, I did an internship. I knew that no one was going to give me a job working in HR because I had no HR experience. I will never forget taking ten thousand dollar pay cut—which was a lot of money back then—to take that internship, and I sat down and did this spreadsheet to say okay, but if I get this next job, I can get a X percent raise every year then by this point, I can make that money back and then I will actually have a career path.
I never had a career path before then. I felt like I was just always treading water until I was 39. I just worked so hard, but I was not getting ahead, when I went back to school—that was the game-changer combined with the fact that I was very lucky to have some bosses and mentors that gave me incredible opportunities; so I still try and pay it forward and provide similar mentorship today.
It kind of boggles my mind to actually think about how old I was when I did that. I don't think you girls realize how scrappy I had to be. Raising you guys. Working almost full-time and going to school almost full-time. Driving so many miles. There was just no sleeping. I feel like I didn't sleep for years.
KD: What personal unlock do you think you have between your 40s and your 50s?
JH: When I turned 50, that was a huge shift. From 48 to 50 was obviously a significant shift because your dad and I split up. I'd never been on my own like that before, right? Not since I'd been in my early 20s. So that was a huge shift.
Being able to go buy a house, that felt really good to be able to do that on my own. And shifting from being a mom of teenagers to a mom of adults—you guys were graduating from college—and that relationship had to evolve right because you were growing up. How do you let that relationship evolve? Every parent talks about this…it doesn't matter how old your kids are, you watch them do stuff, and in your head you're like, “I wish you wouldn’t do that,” but as much as you can, you gotta let them live and do their stuff and just let it unfold. That's hard to do as a mom.
KD: What has been the biggest struggle of detaching your identity from being a parent versus being a person?
JH: I don't know if you can ever do that. Even if you're not “caretaking” for your kids anymore, you're always worried about them. You can't understand it until you live it.
They are not necessarily living in your house, but they are still living in your head and your heart. All the time. There's not a day that goes by that you're not thinking about, like, “Oh, I wonder what Kayla's doing. I wonder what Brooke's doing.”
KD: I want to talk about your coaching and your journey to getting all your certifications, and how much career coaching you've given me and the people I know. Why did you decide to pursue that?
JH: I think there are two folds to that. It's this thing that's evolving, as I'm hitting 60, I have been striving striving striving striving for years, “Oh if I get this one more thing, that'll help me get further ahead, and if I get this one more thing, that'll you know give me more credentials and allow me to grow my career.” And that was so that I could have financial security, first of all, for my kids. Most of it was about that.
And then at some point it shifts to, “I've got to have financial security so I can retire at some point.” Coaching was a couple of things. First, I've had the opportunity to have a coach and know how impactful that was for me and how much of a difference it made. And then it's naturally part of my job because of what I do. And I wanted to be better at it. Because I know it can make a difference.
Particularly for me, I like helping young women find their path. We all have times when we know we aren’t in the right job situation. As a coach, we don’t have the answers; our job is to ask the questions that help our client uncover their own answers.
Just navigating all the things you have to do in your job can be challenging. Or being in a job that isn't fulfilling. Everybody has to do certain things in their job that they don't like. Nobody has a panacea job where every day is sunshine and rainbows. But you do deserve to be treated with a certain level of respect. You do deserve to be recognized for the work you do.
At the end of the day, part of it is that you don't get invested in creating a big story about what the other person is thinking about. You have no idea what they're thinking. You can waste a lot of your energy on that. You control your energy. It is up to you where you want to spend your limited energy. If you want to remunerate about what somebody said or didn't say, or how they treated you. That's a choice you get to make. Nobody can make you feel a certain way. People can do something, and you're going to have a reaction, which you get to choose. Be intentional about your reaction. That is not always easy to do.
Being intentional is something I'm working on all the time. I've gotten better at it, but it is a work in progress. Pausing, processing, and putting a name on whatever the feeling is. If you can learn to do that, it's very empowering.
KD: So, are you taking clients?
JH: I’m always taking new clients!
KD: Okay, last question. What do you want to bring into your 60s?
JH: Being really intentional about my energy. Definitely being more intentional about my health. I think women have to be way more open about talking about menopause and the impact that it has on them. It has had a huge impact on me. I went through menopause for several years before I actually went to a menopause specialist. That was one of the best things I ever did. I think a lot of women are suffering through it without knowing what to do. You need to educate yourself about what the options are, and different things are right for different people, and everybody's got to make their own choices. But being aware that you do have options, that's huge. It's incredibly impactful.
I want to still be going and doing things, being physically active when I'm in my 80s. If I don't strength train and take care of myself, I'm not going to be able to do that. I definitely know my runway is shorter. You want to be more intentional about how you spend your time. You definitely think about the people you spend time with, people who bring you energy versus people who take energy.
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Thanks so much for reading! Today’s issue was a bit more personal, but I’ll be back next week with our classic format. In the meantime, I’d love to hear from you in the comments what birthday traditions you practice. I’m coming up on my own in a few weeks, and you know that means we’ll have lots of Virgo energy and birthday trip advice infused into future editions! xxKD
Love this so much, I absolutely need to interview my mom. And the gift ideas are great!
Loved this!! Makes me want to interview my mom when she turns 60🥹