Ep #266: Regret-Proofing Your Future

The Design You Podcast Tobi Fairley | Regret-Proofing Your Future

Welcome to today’s episode, where I’ll be sharing some personal insights on how I’m taking control of my future by regret-proofing my life and business. It’s never too late to start, and I’m excited to inspire you with stories about my new side gigs, which I’m starting up with my family.

Join me as I reveal how I’m working with my mom and daughter to pursue our passions and build successful businesses together. It’s a journey filled with ups and downs, but the reward of knowing that we’re creating something meaningful is priceless. And the best part? We’re taking steps to ensure that we won’t live with regrets in the future.

Are you looking for ways to regret-proof your life and business? Tune in to hear my personal experiences and get inspired to take action toward your own regret-proof future. Whether it’s working with a loved one or taking on a new challenge solo, this episode will provide you with valuable insights on how to make the most of your opportunities and live a life with no regrets.

My new e-commerce shop is launching on June 1st 2023! Follow Fairley Fancy on TikTok and Instagram to follow along with the launch, stay up to date with details of giveaways, and all the good stuff.

If you’re an interior designer or creative looking to up-level your business, I have something for you. It’s my Build a Better Business Guide. Burnout, undercharging and the feast and famine cycle are rampant in the design industry but there’s a better way to run your business. Click here to get my manifesto and guide that will have you on your way to a business with more ease, more joy, and more money.

What You'll Learn From This Episode

  • How I’m regret-proofing the future of my life and business.
  • Why starting a business with my daughter is the perfect empty-nest project for me.
  • The joy I’m getting from building businesses with my family.
  • Why, no matter what age you are, you still have time to regret-proof your life.
  • How to see the things in your life that you might regret not doing.

Featured On The Show

Full Episode Transcript

You are listening to The Design You Podcast with Tobi Fairley, episode number 266.

Welcome to The Design You Podcast. A show where interior designers and creatives learn to say no to busy and say yes to more health, wealth and joy, here’s your host, Tobi Fairley.

Hey friends, welcome back to the podcast. I am so happy that you are here. So as I’m recording this episode I just got back from six days at the High Point furniture market a couple of days ago I got back. And I’m so happy to have a long weekend of rest coming up, you have no idea. And if you know about High Point Market, it is both amazing, and it’s brutal, it’s awesome and it’s awful. It’s not awful really, but it takes a toll. And so I’m happy to be back home.

I used to always take time off when I got back from High Point which was smart and I kind of forgot about it. I guess, I don’t know, the pandemic made me forget a whole bunch of good things that I started back in the day. And so I’d take a couple of days off after market because otherwise I was pretty worthless the few days after I got home. Well, this time I told myself I didn’t have a choice, I had to keep working because there was so much to do, and guess what? I was still pretty worthless the last few days. So my work has been subpar.

And so yeah, instead of just letting myself be exhausted and rest, I pushed myself through to work. So we’ll see what comes of that work I did this week. I might look back on it next week and think, yeah, no, that has to be redone but we’ll see. Anyway, next time I’ll take time off, but that’s not what today’s podcast is about.

Okay, so yes, that’s a good reminder that in the fall I’m taking two days off when I return. And I’m going to lay in the bed and do nothing and that’s going to be important because of all the things I’m working on right now which is sort of what this podcast is about. So this one’s a little bit personal but it’s just I want to share a story with you, a couple of stories and then remind you to really lean in to the things that matter. So this is probably a short episode, hopefully a powerful one. But yeah, just getting us back to the things that matter in life.

So you’ve been hearing me talk all about the two side gigs I’ve got happening right now that are going to be opening sometime in the future, one has a date, I’ll tell you about in a minute, one does not. But those two side gigs are my new ecommerce store that I’m doing with my daughter and also a short term rental business that I’m launching with my mom. And so at market last week I actually attended a conference, sort of a conference within a market or a conference within a conference as you would say called The Vacation Rental Designers’ Summit.

And I also spoke at this summit. And it was really, really good, the conference was amazing. It was their first time to do it. I learned so much about short term rentals and I met so many amazing other designers and people working in this area. It was really, really great. And for my talk, what I did, I was the very last speaker of the event of the whole summit. And I spoke on building a hospitality brand, because as I said to them, “No, I’m not an expert yet in short term rentals, but I am an expert in building brands and creating revenue streams.”

And so I really just took people into a peek at the hospitality brand I’m building with my mom right now, which we’ll be telling you more about in the future. And the reason we say hospitality brand and that was my whole talk was really about how your competition as a short term rental proprietor or person who owns these properties is not really the rental business.
It’s really the hospitality business because your competition is hotels and things like boutique hotels. So I really gave people a peek at the hospitality brand that we are building which was so much fun.

And here is what this podcast episode is about. Right after the talk, after my talk, as the conference was wrapping up, someone that I’ve known in the industry a little bit sort of, we’ve known each other through social media, came up to me and said and she had tears in her eyes.
And she said, “I just want to tell you how special it is that you are doing this with your mom.” And so I’m going to tell you more about that in a second because it’s really what I want you to be thinking about, this idea of regret-proofing your life and your business.

Because this particular designer was saying and she even spoke about this during her presentations. She was one of the other speakers at the short term rental conference, that her mom had Alzheimer’s. And so she said they were really close but they never got to do the type of things that my mom and I are doing together. And it really was special to her to see what we’re doing. But she just wanted to make sure that we knew how special it was and that we cherished every moment of that. So there’s that, put a pin in that for a second. I’m going to come back to it.

And then I’m going to remind you the other side gig that I’m working on right now is my new ecommerce business with my daughter and my mom’s really nothing with a lot of that too. I hardly do anything that my mom’s not a part of. But, Ellison and I are doing this together as our business. And yeah, so mom’s been beside me all 25 years I’ve been in business and she’s continuing to be beside Ellison and me as we make lots of decisions and it’s really great.

So the ecommerce which we will start fully promoting one week after I record this. So by the time you’re listening, we’re full-fledged promotion of the ecommerce shop. And it’s called Fairley Fancy. And I’m going to do a whole podcast episode in a couple of weeks about the process of creating Fairley Fancy, including how we picked the name, why we picked the name, what all has been involved in building the business, how my daughter and I are working together in that business. So that’s coming up soon.

And that episode will come out the week that we launch or maybe the week before, but we’re launching June 1st. So in the meantime before you get to hear that podcast episode I’m going to go ahead and tell you now and I’ll tell you again later in the show to head over on Instagram and TikTok and follow Shop Fairley Fancy. So on Instagram it’s @shopfairleyfancy. I think on TikTok it’s just @fairleyfancy, but the name of it is Shop Fairley Fancy. So you’ll find us with that moniker.

And if you follow us on those platforms you’ll get to come along for the ride as we start to announce all the fun things we’re going to be doing. We’re going to have some awesome giveaways. We’re going to start to talk about the vendors that we’re carrying and a lot of the things we’re doing. So follow us there to find out more and stay tuned for that other episode.

But I promise that this whole point of having two side gigs is what this episode today is talking about. So let me get more into that. So just after I finished my talk as I said at the short term rentals conference, the designer came up and told me her story and about how she had dreamed of being in business with her mom but she wasn’t able to. And I love that my mom and I are doing this side business together. I’m 51, she’s almost 75, she will be in a few weeks.

And this is such an amazing reason to keep us both connected to each other and to keep us both young and to keep us both excited because we love a project. We love all things design. We love all things hospitality. We love to nurture people. And it’s just such a joy to do this with my mom. But mom has really not only helped me in my business for the last 20 something years, almost 25 years. She has had many businesses herself, not just the business that my dad has that he runs, our family business.

But mom has had everything from a clothing store when I was really young that she had in South Arkansas. Then she was a buyer for and really ran the sort of gift shop and sales part of a pharmacy that my dad’s parents owned. So I remember her buying all this fun stuff at market and merchandising, all of that. She was so good at that. She also had a job as a piano teacher somewhere in between because she is a pianist and so she taught other kids how to play. And so she’s done all sorts of things and it’s fun to think about that because a lot of people know her as my mom.

But she is an entrepreneur in her own right. She has been doing this stuff way before I did. I don’t even know, I’d have to go back and find out when she started her businesses but I’m guessing before I was born because I know she did have a dress shop when I was a really little girl. So she is an entrepreneur herself and now it’s so fun that we are starting really a partnership. Because in the past with my business it’s really been my business although I’ve leaned on her so much. So this time it’s our business which is so fun.

And it’s going to cause me to do things a little bit differently. And I know I’m going to learn a whole bunch from it. And what I’m most excited about is that we’re both going to do this at the ages we are because age is just a number. And we have so much fun still to create in our life. So if all of that weren’t special enough all by itself, just the week prior to me having that encounter and conversation with the designer about how she wished that she had done something with her mom, I had a similar conversation about the ecommerce shop I’m launching with my daughter.

So I was on a coaching call with my coach, Suzie, my life coach. And she was basically saying the same thing about building this shop with my daughter. She was reminding me because she is a coach for midlife women and she does a lot of work around helping people regret-proof their life. Because when they get to midlife they’re kind of thinking about what their legacy will be and what they want to do with the rest of their life. And so she spends a lot of time helping people really regret-proof their life.

And so what she was reminding me is that by building something with my daughter and for my daughter is really not only a perfect strategy for regret-proofing it’s also the perfect strategy for empty nesting. And it’s the perfect, as she called it, empty nest project for me.
Because she reminded me that most people when they’re sending their kids off to college, especially if it’s an only child like mine or the last one to leave the nest, a lot of times those moms or even both parents are finding themselves without a lot of direction and finding themselves feeling old and obsolete and sad and wondering what’s next for them.

So in typical Tobi fashion, I am doing none of those things. I’m not wondering what’s next. I’m not feeling old and obsolete. I’m not thinking I’m going to be bored. I’m starting two side gigs, one of which is with my daughter. So no typical empty nest things for me because not only have I started this new side gig, I’m starting it with the child that’s leaving and it will be a reason for us to stay super connected even with her a few hours away as we build this business and this brand together which is so fun.

So I know some of you have heard me say earlier in the year when I was talking about these new things that were coming that I’ve never really felt more creative. And that’s still true. And it’s been a long time since I’ve been this excited and motivated in my business. And there’s just something about being a mom that’s building a business that your child might be interested in, that gives you a completely different kind of fulfillment.

And I’m very clear that over the next four years there is a possibility that Ellison might change her mind and not want to do this and that is totally fine. I’m making sure that anything I’m building I would still be willing to keep myself and do myself. But at the same time bringing her in to this endeavor so that it can be about us and for us not just my business that she happens to go to work in. So it feels like such a joy to do this knowing that it could be something of value for her.

And that just reminds me how my mom, I’m sure, has felt all these last 20 something years supporting me in all the things that I’ve done. So for a long time I was really not attached at all to the idea of Ellison and me working together. I knew there was always a possibility because I knew she was a creative but she spent many years telling me that she was not going to be an interior designer and she was not going into business with me. And I always thought she would be something like a make-up artist which she still may absolutely be.

She at one point thought she might want to go to cosmetology school. She’s definitely always been interested in fashion and I knew that there was a huge possibility that fashion could be part of what she was going to do. And that’s what she is currently moving towards. So she starts college in just a few months and she’s studying apparel, merchandising and construction. And though she is a bit more interested in interior design than she used to be, because she’s always the one saying, “Hey, can we watch a design show?”

But now we’re building this boutique that is so fun, an online boutique and then a small physical store. And it’s a combination of home decor and apparel all under one roof. So it’s the perfect combination for the things that we both love. And I have to tell you that I do absolutely love fashion and I absolutely love buying for a shop and putting together the product mix and the branding for the store and the social media plans and all of the things that we’re going to do to sell our products.

So it is still exciting to me. And it is still something that I love all by myself, but the two of us together, getting to combine sort of our first love, each of us in our own lane. And then also be interested in the other side, her and somewhat in design and me still being interested in fashion. It’s going to make it really, really fun for both of us to be able to have a lane and to shine and to build this together. So there’s something great about selling apparel with home décor.

I’ve heard this from many people as I started buying apparel and telling them I’ve had this design business for 25 years. I had a retail store for 10 years. We’re getting back into that space. Things have changed so much. You have all the opportunities now with ecommerce that didn’t exist when I closed my physical store about 14 years ago.

But so many people have been telling me all of the stories about these small boutiques all over the place, especially across the south that bring apparel into their home decor businesses because people need to buy clothing or want to buy clothing way more often than say they want to buy a sofa.

And so it is the perfect combination of things that bring people in often and give you a mix for your social media and for connecting with clients which is absolutely wonderful. Because it gives you a reason to be engaging with people, your community, your customers, your buyers on the regular, at least seasonally, summer, spring, fall, all the times that people are going to buy a new wardrobe. But also giving people other reasons to come back to you for home decor and bedding and pillows and gifts and furniture and all the things.

So I’m saying all of this to circle back to the point that I started with sort of, about regret-proofing your life and your business because I want you to be thinking about whether you have a kiddo like me or a mom like me that want to be in business with you. What is it that you’re doing right now in your own life to make sure that you don’t get to the end of it or to a point in the future that something you’ve dreamed about or would have loved to try or enjoy has passed you by, that it’s too late or that somebody’s no longer here that you could be in business with.

Or somebody’s moved on to some other endeavor and it doesn’t make the timing really right. So I want you to really think about that. And maybe it’s just you all by yourself and you don’t have anybody you want to partner with. But there’s something that’s big and scary that you’ve just been dreaming of but you’re not going after it. That is what I want you to be thinking about because you still have time, no matter what age you are, to regret-proof your life, to leave the legacy you want to, to try the things that you’ve wanted to try.

And this is me reminding you and encouraging you that you can absolutely be doing that. I have had some of the most wonderful memories with my mom over the past 24 years of me running my business. And we have traveled the country. We have gone everywhere where I’ve been speaking at markets or putting on events or buying for our clients, our design clients, or buying for our retail store that I had for 10 years. We’ve done all the things. We’ve done showhouses in The Hamptons in New York City. And we’ve worked with business consultants all over the country.

And every single time we have gone to a different city for one of those reasons that my business brought me there, we have had so much fun along the way. I have a friend who owns a boutique and she’s all business and she did it with her dad and they were all business. And that is not at all how my mom and I have done this.

We have made sure that every single city we’ve been to, that we’ve gone to events, and the best restaurants and shopping and Broadway plays and all of the stuff that has been so special and so meaningful. And it’s just such beautiful experiences and our hearts and our lives are so full because of where our choices with my business have taken us and we’re not done yet. And the fun thing is that we’ve taken my daughter along with us on so many of those adventures and especially when she was young, it made me so happy and so fulfilled to have her there with me.

So I always say my two favorite girls, my mom and my daughter. They have been there with me all along the way. I remember Ellison’s very first trip to New York when she wasn’t even two years old yet. And I remember how we had her dressed perfectly in her brown velvet jeans and her fluffy white snow boots because it was cold and her little cream colored Burberry jacket looking the most adorable that you could possibly imagine with a big bow in her hair.

And not only did she come along with us then, she is still coming along with us. She just came to High Point Market with us last week. And it is still such a joy to be with my two favorite girls. So this year alone, mom and Ellison and I have gone to apparel markets for buying trips twice. We’ve gone to two furniture and gift markets. So we went to Dallas furniture market or gift market, well, gift and home décor. And we just went to High Point and you all, it’s only May and we’ve already had four amazing trips together just because of the store.

And we have two more trips planned just this summer for markets that we’re going to be buying and scouting and doing all the things. And I can see, God willing, that all three of us stay in wonderful health and are all still interested in this, that we have many, many, many more years of fun ahead of us, thanks to businesses that we’re building together. And for that I could not be more grateful. And I have to agree with Suzie, my coach, that this has helped me regret-proof my life in so many ways. And you all, I hear over and over and over again from people and I’ve heard this for years that they are so amazed at the relationship my mom and I have.

And I always laugh and I said this at 30 and I said it at 40 and I’m still saying it at 50, I take my mom everywhere I go and they laugh, but they wish that they had that opportunity. And now Ellison is starting to hear that same thing from her friends saying, “I love how much time you spend with your mom and it’s so neat. You get to do all these things with your mom and you travel with her and you’re doing this business together.” And I have always enjoyed my mom’s company just as Ellison has enjoyed mine.

And when I was growing up and in high school I really most of the time wanted to be with my mom more than my friends. And I find a lot of times, not always, but a lot of times that’s Ellison’s experience too. And again I know that not everybody has this. Not everybody’s moms and daughters are still here, not everybody has the privilege of having this sort of relationship with their mom or their daughter. And we have been very blessed with good health but we’ve also worked at being very close to each other. We’ve chosen to do this work together.

And it definitely helps that all three of us by nature are creatives, that we enjoy the same types of things, that we all love design and fashion and we have a similar eye for style. And to be honest, on a side note, I credit my mom with that eye for style. I’m the one who went to design school but she was the one that had that innate gift all along. And I think that our sense of style and design abilities really are innate. And mom was definitely born with that gene.

She literally has a gift for understanding quality and construction and color and all of the things that really go into creating beautiful spaces and beautiful clothing. And she’s really understood that her whole life. Even though she came from a very humble background. Her family was not affluent. But she always had this gift for both fashion and understanding color.

And you all, it is uncanny, we can literally be in New York City and I can say, “Do you think these shoes will match this dress I have at home?” And she’ll say, “It’s exactly the same color or no, I don’t think so, I think it’s slightly off.” And whichever one she says, you all, she’s always right. She really has that eye for color and she passed it along to me. And I do believe and have long believed that she did pass that gene down. But she also taught me a lot of this, things like construction and quality and what in fashion about form and construction and pattern matching and all the things, mean quality.

And so over the years I think I maybe started to believe that it was more about what she taught me than a gene, but then when my daughter was born, I was like, “Oh, no, it is definitely a gene because she had it too from a very young age, way too young for me to have taught her yet.” And so I would say somewhere before the age of 10, she knew exactly what style she loved. she knew exactly what looked good on her. She knew when other kids were loving flashy sparkly things and ruffles all around the bottom of their pants, that she was tailored and she got that.

And she would express it to me and I wasn’t expressing it to her, she was expressing it to me. She’s always had that sense of style. And she has been exhibiting it for years and at a level that is so mature and so sophisticated way beyond her years. An example of this is just a few weeks ago she had prom and I think everyone assumes that I’m probably the one helping her with her wardrobe or that I pick out her clothes or whatever, but you all, it is all her. Now, I agree with her choices because we do have similar tastes.

But you all, I have never seen so many people comment on a dress as they did with her prom dress. It’s one of those iconic ones that’s going to go down in history and I had a few of those too, that we will never forget. And it has been so fun to see how many people are still talking about it. When we were at High Point, that is what everybody said. They were telling me that all week and she wasn’t even there yet. And then after she flew in and people saw her, the talk of everybody was, “But your prom dress.” And so that was so much fun.

One of the compliments I love the most was from a friend, Emily McCarthy, who has her own clothing line and we’re carrying her clothes in our store in Fairley Fancy. And she sent me a message on Instagram and said, “That dress is hands down the best I have seen of all the prom dress picks I have seen anywhere.” And she was talking about people she’d seen locally and her own friends and the people in her social media feed which was such a beautiful compliment because I adore the fashion collections that Emily is creating so much so that’s why we’re carrying them, and she gets it too.

And so to get that compliment from her was really fun. But my girl got the fashion gene, you all, she got it. She is bold. She is confident. She wears things that her friends would never wear. If it’s bold or glamorous, if it’s a big puff sleeve or made with organza and a big bow tied at the neck, you can sure bet that she’s going to be willing to wear it and have so much fun doing it. And I have loved this about her for a long time. When so many preteens and teenagers were trying to fit in and not stand out, she is always the one doing the opposite with her wardrobe. It’s really been one of her main expressions of creativity.

So thank you for indulging me today, for listening to these stories, for listening to the connection and the experiences I’ve had with my mom and my daughter and why we’re on the same page and the genes that mom handed down to us. Because these two side gigs that I’m building are really about me, yes, but about my two partners in crime, my mom and my daughter and how we’re regret-proofing our lives by going after what we want but doing it together which makes it so much more fun.

I mean Ellison’s not even in college yet. She’s just turning 18 in a few weeks and we’re already building a business together. And my goal is that if she does fall in love even more or with this path as she goes and studies fashion, merchandising and apparel. And if this is truly still her dream to have this apparel boutique that by the time she gets out of college I will have helped her and helped us. She and I, build this fairly fancy brand into something that is very successful and that supports her to continue to live her dreams.

And I know, you all, that there is some fashion design in our future. We are not just selling other people’s things. But we’re definitely starting to dip our toe into what it’s going to take to create our own lines. So that I’m sure will be happening in the future which is also so much fun. And I just want you to remember that again whether it’s you or your child or your parent or a sister or someone that you’ve been dreaming of working with, even if it’s just you by yourself. And you’ve thought about launching the thing or creating a clothing collection or doing something in design.

You absolutely can do it and I want you to remember to take the chance. And really regret-proof your life in the same way. So in the meantime, don’t forget to go follow us on Instagram, or TikTok or both @shopfairleyfancy on Instagram. You can follow along with our launch and all the things we’re doing. And we cannot wait for you to see the store, the online version, maybe the in person version sometime too. And we can’t wait for you to be one of our customers. And we are just super excited.

Alright, friends, so I’ll see you with another episode about this collab that we’re doing in a few weeks. Next week I’m going to be back here with a different mother daughter episode, a different mother and her daughter and a collaboration they did which is just in time for Mother’s Day. I thought these two episodes were the perfect thing to lead back to back for Mother’s Day. So I’ll see you here next week with that other Mother’s Day episode, but in the meantime follow us on Fairley Fancy and we’ll see you back here real soon. Bye for now.

Thanks for listening to The Design You Podcast, and if you’re an interior designer or creative looking to uplevel your business, I have something for you. It’s my Build a Better Business guide, because burnout, rampant undercharging and the feast and famine cycle are epidemic in the design industry. And there’s a better way to run your business.

So head to and get my manifesto and guide that will have you on your way to a business with more ease, more joy and more money. That’s

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Hi! I'm Tobi

I help creative women (and a few really progressive dudes) design profit-generating, soul-fulfilling businesses that let them own their schedule, upgrade their life and feel more alive than ever!

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