EPISODE 154 | MARCH 06, 2024

Making Courageous Transformations with Alison Jacobson

Embark on a transformative journey with Alison Jacobson, the “Midlife Maverick Podcast Host,” as we explore the landscapes of resilience, empowerment, and personal reinvention in midlife.  Alison opens up with Host Natalie Benamou, about her triumphs over adversity and how she channels her experiences to inspire and empower women to craft a bold new chapter in their lives. Get ready to dismantle the limiting beliefs that hold you back and embrace the wisdom that comes with midlife, all while forging a path of greatness and fulfillment.


  1. Resilience is not just bouncing back from adversity; it's about using those experiences as a catalyst for profound personal growth and empowerment.
  2. It's never too late to redefine your identity, chase your dreams, and start anew, whether it's starting a business at 50 or running the New York City Marathon.
  3. Happiness and success in midlife are defined by your terms—envisioning your perfect day, setting specific goals, and surrounding yourself with supportive people are key to making it a reality.


“You can start that business at 50 years old, you can go back to school, you can leave your partner, you can do whatever you want in your own way.”


“Live it the way you want to, without fear, without excuses, without deference to anybody. Be that bold, badass person that you want to be.”

“I celebrate because I would not be who I am today if all of those things hadn't happened to me.”

This podcast is sponsored by HerCsuite® NEXT a mastermind circle for women leaders discovering their 3.0 career. Each month Circle Chair Lynn Whitesell leads the discussion with speakers and breakout sessions exploring defining moments.

Keep shining your light bright. The world needs you!

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About Alison Jacobson

Alison Jacobson is a coach, speaker, author, and host of the podcast Midlife Mavericks. She empowers women in midlife to conquer self-doubt to confidently achieve their goals and unlock the success they deserve.

She’s built three multi six-figure businesses while managing the role of caregiver for her son with Intellectual Disabilities and her husband with MS. Her journey includes conquering the NYC Marathon at 57, proving it’s never too late for transformation.

I coach women on how to get past their limiting beliefs, learn to prioritize their own happiness and success and confidently achieve their goals.

I specifically help them reframe their mindset around financial lack in order to feel empowered to grow their business.

Transcript episode 154:

Redefining Midlife: Redefining Midlife: Courageous Transformations with Alison Jacobson

00:00 – Alison Jacobson (Guest)

I was transforming into midlife and I wanted to help women who thought their life was ending. They didn't know who they were, what they wanted to be after the role of mom and partner and caregiver, and was really questioning what that next chapter was. And I wanted to help them remember those dreams they had before they took on those roles and find the self-confidence to get past those limiting beliefs, that imposter syndrome, what everybody in society is telling us who we are in midlife, to live these bold, courageous, kick-ass lives. And that's how the midlife maverick was born. And I have been now doing this for four years and just loving this group of women. I am finding and empowering to say you can start that business at 50 years old, you can go back to school, you can leave your partner, you can do whatever you want in your own way. 

01:01 – Natalie Benamou (Host)

Welcome to HerCsuite® Radio for Women Leaders on the Move. I'm your host, Natalie Benamou, and every week I bring you inspirational stories and valuable insights to help you advance and thrive in every area of your life and your career journey. Today's guest is going to be talking all about her life and her career journey, and it's going to really resonate with you. Alison Jacobson is a coach, speaker, author and host of the podcast Midlife Mavericks. She empowers women in midlife to conk herself out, to confidently achieve their goals and unlock the success they deserve. She's built three multi-six figure businesses, while managing the role of caregiver for her son with intellectual disabilities and her husband with MS. Her journey includes conquering the New York City Marathon of 57, proving it's never too late for transformation. I know you are going to feel so inspired after this conversation, so let's get started now. Alison, I'm so excited to welcome you to HerCsuite® Radio today. Thanks for being on the show. 

02:26 – Alison Jacobson (Guest)

Thank you so much for having me. This is such a great audience to speak to. 

02:32 – Natalie Benamou (Host)

We found all the synergistic ideas before we got on to this interview. But for our audience, who don't know all the things about you and you've had an amazing life and arc of a career I always like to start with the first question, which is talk a little bit about the arc of your career and what's bringing us to this moment today. 

02:52 – Alison Jacobson (Guest)

Wow. My life has been defined by tragedies and obstacles, but it's also something that I celebrate, because I would not be who I am today if all of those things hadn't happened to me. So the first thing was, unfortunately, in 1997, my first son died of sudden infant death syndrome. My second son has intellectual disabilities. I have two daughters, and after my second daughter was born I realized my marriage was not good. It was emotionally and verbally abusive. I decided that is not what I wanted my daughters to see. So I decided to end the marriage. But I was the breadwinner, I was bringing home the bacon and it cost me every cent. I had to declare bankruptcy after that. It was really traumatic. 


Fortunately, I met and married an amazing man on match, yes, it is possible. But four weeks after we were married he was diagnosed with primary progressive MS, and so I went from being a new bride to a new caregiver in the matter of four weeks, and so I am a caregiver for three generations of my life my mom lives with us, my husband with physical disabilities and my 25-year-old son with intellectual disabilities. But despite all of that, once you have recognized you've lived through some of the worst fears known to anybody and you can succeed and thrive. It has motivated me to help other women, because if I can help one other woman who's doubting herself, who is scared, who feels like they can't do what they want to do after they hit 40 or 50, I'm here to say it is possible. And so I coach women. I have a podcast, midlife Mavericks, I am a speaker and I have my book, daily Inspirations for Midlife Women: a guide to peace, joy, confidence and abundance. 

04:49 – Natalie Benamou (Host)

And the positivity that you just shared. Considering all of the things that you faced, I think it really speaks volumes to how we can approach the world and even in our darkest moments, if we can find a light, that is what is going to guide us through and amidst all of this, you've also had an amazing career trajectory as well, and I want to talk a little bit about that, because there have been ebbs and flows along the way with the things that have happened to you personally. Can you share a little bit about that journey as well, because I think it's really important to see that, amidst this, that we are this whole person and that we can do these things, even when. 

05:30 – Alison Jacobson (Guest)

Yeah. So I moved out to Los Angeles when I was right out of college. I wanted to be in the entertainment industry and found myself in the entertainment PR business, and at 24, I opened my own PR firm. I had four women working for me, I had this beautiful office overlooking Venice Beach and at 28, I actually sold that business to a multinational PR firm. And what's so interesting about that is, literally three weeks before they approached me, I was having lunch with a friend who said it's great to have your own business, but what's your out game? And finding someone who wants to buy a small company, it's just not going to happen. And three weeks later it did and I went into corporate America. 


I loved that for quite some time, but then my first son died and my second son was diagnosed with intellectual disabilities and I realized I needed to be home. I needed to find a new way to work that allowed me that flexibility. And because of those instances and passions, I realized I wanted to talk about child safety and family safety, and so I decided to start really talking about it. I started a blog, I started speaking all over about this and again I was told well, that's great, but without a book, you're never going to get on TV. You're never going to be that spokesperson. Well, I took a financial chance. I hired a PR firm. Within literally weeks she had me on Good Morning America, she had me in the Wall Street Journal, she had me in USA Today and all of a sudden I became known as the safety mom and I built a spokesperson business. I was the spokesperson for Cox Communications for many years. A lot of high end. I did a lot of satellite media tours and it was fabulous. I loved what I was doing. 


But then the arc came. My kids got older. I went through that divorce. I was now a caregiver and the safety mom wasn't really my sweet spot anymore. 


And as I was getting into midlife and starting to experience menopause and experience all of those things of becoming an older child taking care of my parents, I was transforming into midlife and I wanted to help women who thought their life was ending. They didn't know who they were, what they wanted to be after the role of mom and partner and caregiver and were really questioning what that next chapter was. And I wanted to help them remember those dreams they had before they took on those roles and find the self-confidence, to get past those limiting beliefs that imposter syndrome, what everybody in society is telling us who we are in midlife to live these bold, courageous, kick-ass lives. And that's how the midlife maverick was born. And I have now have been doing this for four years and just loving this group of women I am finding and empowering to say you can start that business at 50 years old, you can go back to school, you can leave your partner, you can do whatever you want in your own way. 

08:53 – Natalie Benamou (Host)

Doing whatever you want in your own way. I mean, this is why we're like fast friends, because I left my career of 29 years in the pandemic after being in my early 50s, and it takes courage, but it also takes being surrounded by the right people, and that was really what Hershey's Suit was started, as is, I believe, were the results of the people we surround ourselves with. Was there anyone? You mentioned your friend earlier who gave you the sage advice that you wouldn't be able to sell? But have there been people in your circle going through the things that you've gone through that have really helped you along the way? 

09:29 – Alison Jacobson (Guest)

I had to cultivate them. I really had to, and I'm sure this is something you can relate to. So much of what holds women back is their mindset. The mindset and the stories we've heard that we're not capable of doing this at a certain age. All of those stories and a little side note. So I'm now the CEO, as well, of the nonprofit that helped me when my son died of SIDS, its first candle, and we are one of the charity partners for the New York City Marathon, and so I've gone to the New York City Marathon every year. 


And two years ago I said you know what? I'm going to run the marathon. Now, keep in mind, I've never run a mile in my life. And I said I'm going to run the New York City Marathon when I'm 60. And all of a sudden I stopped myself and said that is just procrastination, that is a limiting belief. I'm stopping myself. No, I'm going to run. This year it was my son's 25th angelversary and I said I'm going to do it. And I went home and I told my husband at the time I'm going to run the marathon. He's like oh, I don't know, honey, that's tough. And I said game on. 


And through that whole experience of running the marathon, of training for the marathon, I learned that there were certain people I had to kind of keep at a safe distance because they weren't going to support me. They didn't understand why I was doing what I was doing. All of that, and even my daughters for a while, were like mom, you're 56 years old, are you sure you want to do this? And they meant it lovingly, but I had to keep them at a distance and I had to find my tribe. I had to find those people that were going to say, yeah, and that's the same in business. Right, there are those people. 


So it's a staggering to me that we ask opinions or get advice from friends and family who have never opened a business, who have never been an entrepreneur, and we take their advice when they don't even know what it means to do this, rather than looking to those other people. And you do, like your team. Your group is so important because we do need to find those people that support us. As a speaker, I'm part of a group called Innovation Women. I love it because there are speakers that have been speaking for many more decades than I have who are saying of course, you can do it, come to us. We're going to support you. We're going to offer you free advice, help you whatever way, and that's what women need to do. 

11:57 – Natalie Benamou (Host)

And Bobby Carlton is one of my favorite people. She's an alliance partner, so we'll be talking about that too, and I should have realized that you're part of Innovation Women because you're an amazing speaker, so that's awesome. And it's true that when you find women and Speaker friend Friday we're recording this on a Friday and there's two today. One is West Coast and one is East Coast for those listeners. If you want to join Innovation Women, I will have a link in the show notes, but I think it's so important and we were talking and I did my 5K. 


Okay, so I was not when you ran their marathon, I did my 5K. However, I was running in a town that I didn't know. I barely have ever been there, but a friend of mine and a mentor and part of she's a founder of her C-suite lives there. It's called Oak Park, and you run through the town and you get to see all of Frank Lloyd Wright's houses. That's like the 5K. And I was like I am going to run that 5K. 


So I started training in the summer and like trying to get ready, and on the day it was freezing cold, so I was like I'm not prepared for not being able to breathe. But here I am running along and there's Wendy and her mom and they're cheering me on as I'm running through Oak Park right by her house, and I ran by and I so that's what made me think of it, because when you have that person, you need a hundred, one or two good people that are there. And she was like let me take your picture, and I kind of ran slow motion so I can take a picture. And it was just when you surround yourself, it is so important to be with people that lift us up instead of bring us down. 


And, to your point earlier, when you're with people that don't have experience, they're trying to protect us. I think they mean well, so maybe, but on the other hand, maybe not, and so it is important to do the guardrails. What would you say to someone and I'm sure you tell this to your coaching clients and others but how do you recognize the people that might be pulling you down? So you made that, you listened to what people were telling you and you're like I'm gonna do this anyway. How can, what can you tell women to know when it's time to maybe make that distance, cause it's hard for us to not have our girlfriends or not have that person. 

14:10 – Alison Jacobson (Guest)

Well, I liken it to there's different friends for different occasions and you know, you can feel it in your gut when you call somebody all excited about something you're gonna do, and they're flat or monotone or whatever. Those you get that feeling. And so it's not that you can't have these people in your life, but they have to be your girlfriends who you go hiking with, or they have to be your girlfriends who you have brunch with. They're not your work girlfriends, and so it's okay to have those people. And it's especially difficult with families coming out of the holiday season when you may be visiting these relatives and talking about building your entrepreneurship. 


I know that was the case in my family. My family, solid middle class, all nine to five, blue collar, especially my parents' generation was you stayed at the same job for 30 years. You got that gold watch. You never rocked the boat, and so I was this unicorn that they didn't even know. And God love my mother. She's very supportive, but she didn't get it. She didn't even know how to be supportive of me, and so I learned that I just didn't talk about those things with my family. Kind of the same with my husband. Right, my husband supports me, but when I'm creating a new coaching package or a new program, I don't talk to him about it till it's done, because I'll get a lot of those comments of well, did you think about this, did you think about that? And it's like no, no, no, no, no, no, we're not gonna go that half glass empty. So you don't have to ditch the friends, but you do have to compartmentalize them. And it's interesting, and I'm not sure if you felt this way running the 5K. 


But my speaking presentation is all about the life lessons I learned running the New York City Marathon and I talk about the four Cs. But one of the things that's so important for women is not only the mindset of whatever you wanna do to succeed, but also the mindset of seeing those obstacles along the way. Because if you are only focused on the success of your business and you don't see those nights where your computer crashes and you lose that whole presentation or your biggest client disses you, you're gonna give up. And so when I was running the marathon, not only did I see myself crossing that finish line, but I saw myself at mile 16, because, I was told, mile 16 is hard, it's a slow incline across the Queensboro Bridge and it's silent and all you can hear are other people's feet running. And I also knew that entering Central Park was also a really hard time, so I envisioned myself at all of those hard steps along the way, as well as that success, so I could plan for it. 

16:52 – Natalie Benamou (Host)

I think that mental preparedness is so important and envisioning all the outcomes, because you are gonna hit. I did not do that I should have, because we were talking, it was raining, I was cold, I could barely breathe, I was over optimistic. I was at the front of the line thinking like I was in like 10 seconds. I was like mid group. I was like, okay, let's just try not to be last. That was like by the time I finished I was like I'm going to finish before those people. I just was like I got there, yeah so. But I think that mental envisioning is so important. What do you tell women in our age demographic? Because we're in the same age group to visualize what the future can look like, because I think that's important too. 

17:35 – Alison Jacobson (Guest)

So I think one of the greatest challenges I find with my coaching clients and this happens all the time Many women come to me with the challenges they have, the obstacles, they're not sure what they want to do, and I ask them one question how do you define happiness? And I can tell you at least 95% of them can't specifically say what happiness means to them. And I walk them through an exercise of envisioning and writing down their perfect day, so much so, of where do you wake up? Is it the mountains? Is it the beach? Is it a townhouse? Is it a big house? Is it a city? Is it a country? Because you need to. 


If you can't completely articulate what happiness is, you can't reach it. And so for any age woman I don't care if you're 45, 55, 65, you need to envision what that means. So for me, as I said my husband has primary progressive MS my vision for the future is a beach house that is completely handicap accessible. It's on one floor. I see the kitchen, I see where it is, I see how close it is to a town for my son to walk to. I have it perfectly envisioned in my head. Now I don't know when it's coming, but I have it envisioned in my head and it's the same thing for when somebody is starting a business. It's so important to identify your target audience. I think many times women go into business saying if it's a new bake shop, I'm going to bake for everybody. Really, what particularly do you bake? Who are you baking for? Who is your primary audience? Because if you don't get really specific, you can't have those goals and if you can't have the goals, you don't know if you've achieved anything. 

19:23 – Natalie Benamou (Host)

Yeah, achieved and celebrate. I think that's part of it. So you did that New York City marathon and then I can only imagine what did you do to celebrate when you went through. 

19:35 – Alison Jacobson (Guest)

Well. So I celebrated at various mile points, and that's how I trained too. So, again, I started at one mile. I was so excited when I hit three miles, and then when I hit seven miles, and so throughout the marathon. What's awesome is there are people cheering with the exception of that bridge, I mean Brooklyn, especially Brooklyn they're just teeming onto the street. The wave of enthusiasm is carrying you. So I was celebrating at those certain mile points the 10k, the 10 mile, the 16 mile. 


To be honest, when you finish here's the trick about the New York City marathon when you've run the 26.1 miles, you end up in Central Park, in the middle of Central Park. You then have to walk a mile out of Central Park and then there's barricades. So you have to walk about another five or six blocks to meet whomever you're going to meet. So you're still there. On top of that, once you finish, your body's on adrenaline. You haven't eaten a lot. The biggest mistake is if you sit down, because that's when the pain starts right. 


So my celebration, yes, and I have a picture I don't know if you could see it right there, it's kind of in the background. It's me with my hands up, screaming the minute I cross that finish line Because remember my and again. The other thing is you have to have a great and powerful. Why Great and powerful? Why is not running a marathon? That may be, but my great and powerful, why was doing it in memory of my son? And so the minute I cross that finish line, I'm going to get choked up. I was like I did it, connor. That was my great and powerful. Why? That was the moment I celebrated. 

21:20 – Natalie Benamou (Host)

I'm getting teary-eyed too. I'm so glad that you shared that story and so sorry for that tragic loss that you experienced and all the things that have happened. It's very uplifting but also makes us mindful to know those moments and what is important what is important to us and to the people around us or to our lives, and how do we honor the people that are important to us. If you had one thing because we've got time for about one more thing to share with our listeners, for ways to figure out who they can either honor or feel inspired or go forward what would that be? 

22:03 – Alison Jacobson (Guest)

Well, first of all I want to say I have a free resource for all your listeners. It's on my site Five Steps to Release Fear and Live Boldly. And that's the tip. We have so many shoulds in our life of who we should be in midlife and who we should be as a woman and who we should be as a certain ethnic group. Let those shoulds go. There are no shoulds. This is your life. You get one shot at it. Live it the way you want to, without fear, without excuses, without defense to anybody. Be that old badass person that you want to be and be beautiful and be abundant and, above all, find peace. 

22:52 – Natalie Benamou (Host)

Well, I will have that in the show notes for sure. I have so enjoyed our conversation, allison. And if people want to learn more about you, I know you're in a lot of places, including Innovation Women, but where should they go primarily? Or all the places you can share? Where should they go? And I'll have the links, don't worry. 

23:11 – Alison Jacobson (Guest)

All you have to know is my site, allison-jacobson.com, and that's 1L and everything else. But you can get to my podcast, my books, everything on Instagram. I'm underscore allison-jacobson and that's the best way to connect with me and I will always answer replies because we are here to support each other and lift each other up. 

23:32 – Natalie Benamou (Host)

Thank you so much for lifting up all of our listeners today, for sharing your stories, and I know that it will resonate with our listeners and also help them. So thank you for doing all of that. I'm really, really grateful, thank you. Thank you for having me, thank you for spending your time with us today. This podcast is both sponsored by HerCsuite® programs, including our Mastermind Next, as well as our private network hubs like Innovation Women's Private Network Hub. You can get all the details for both at HerCsuite.com. I hope, if you found this episode helpful and there were so many key points to help women in the arc of your life, that you share it with a friend or colleague and rate and review so others can find out about us. Keep shining your light bright. The world needs you. 

Natalie Benamou

Welcome! I'm Your Host, Natalie Benamou, Founder, HerCsuite® Network.

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