For Jaime Lynn Curley, success today isn’t about achievement or titles; it’s about alignment. Through motherhood, entrepreneurship, corporate pivots, and seasons of reinvention, she’s learned that success is an intentional choice: showing up where it matters, pivoting when life calls for it, and creating a life that feels tailor made.
Success as Alignment, Not Achievement
What is your definition of success today?
Right now, success to me is when I feel in alignment with what I am doing. That includes how I am showing up in my family life, in my career, in my relationships, and in the situations I choose to be in or avoid. I think success is really just about being intentional. For me, that is what it feels like right now, being intentional with what I am doing and having the choice to do it. That is a gift.
When I started my career, though, it looked very different. I was actually in a completely different industry. I went to school for fashion merchandising, thought I would move to New York, go to graduate school, become a buyer, and follow that traditional path. I took a different direction, but still within the fashion and retail world. I loved what I did and grew there until it was no longer serving me.
I loved my work, but by then I had become a mom with three little ones at home, and I was commuting by train to New York City every week. That no longer fit my definition of success. That is what led me down an entrepreneurial path, where I spent the better part of a decade working for myself and doing things I loved, and what I would consider great success. Then life changed again. My kids grew older, things shifted, and now it is exciting to define success in a new way.
Why Pivots Feel Hard and Why They Matter
What do you think keeps women from stepping into a new opportunity or pivoting from entrepreneurship back into working for someone else?
I think it is often fear of failure. When I coached women during my entrepreneurial journey, I saw that the ones who were willing to go all in and say, “All right, let us do this, I am going to try something new,” were the ones who moved forward. Those who held back were often scared. They did not want to leave the security they knew, and they were afraid of failing.
The same thing applies when looking for a new career or job, which is something I recently did. Was it scary? Absolutely. There were pros and cons to both what I was doing and stepping into a new career working for an organization. But I knew I wanted something different. You mentioned the word “pivot,” and that is something I always come back to, being willing to pivot when something no longer feels right.
I have applied that mindset throughout my career. I spent ten years with one company, then another ten with the next. Each time, I pivoted when I no longer felt in alignment with my personal goals and values.
Habits That Support an Aligned Life
What habits have allowed you to get to where you are in your career, your family, and your definition of success?
I would say consistency, but with habits that actually make sense for me—and they’re different for everyone. The things that bring me joy and help me feel my best usually start with taking care of myself. That means getting enough sleep, eating healthy, and moving my body.
I used to go to the gym every day. I loved it. It was my therapy session and my social hour. But I had to pivot when I started coming into the city almost every day. So I decided to take the train, get off at 30th Street, and walk the rest of the way to the office. It is just about finding ways to keep my body moving.
Wellness is really important to me. I also try to be intentional with my time and fill it with things that matter. I once heard that we all have 24 hours in a day: ideally eight hours for sleep, eight for work, and that leaves eight hours for everything else. Obviously, if you have a family or other responsibilities, that looks different, but it reminded me to fill that time with things that fill me up.
As women, we often deplete ourselves. I am guilty of that too, but I know it is important to keep my own cup full so I can give to others. Wellness really surrounds everything I do. When my health is a priority, I make better decisions and show up better both in my career and in my personal life.
Building a Life That Feels Tailor Made
When you think of designing or creating a life that you love, what does that look like and are you living it currently?
My business is called The Tailor-Made Life. It is a nod to my background in the fashion industry. When I came up with the name, I was designing custom wardrobes for clients, and I started thinking, “How can I design the life I actually want to live?”
It looked different back then than it does now, but that idea has been the underlying theme for every decision I have made over the past decade and a half, designing a tailor-made life for me and my family.
Right now, that means being intentional with where I spend my time. I am not always perfect at balancing work and life, but that is something I really focused on when taking this job. I asked myself, “How can I truly be present at work, and then fully be home when I am home?” Setting boundaries has helped.
I will always have that entrepreneurial spirit. It is who I am. But I also recognize how fleeting time with my family is. Designing a life I love right now means being in a career that fulfills me, makes an impact, and creates community, whether through friends or peers. It is about celebrating others’ successes and spending meaningful time with my loved ones. That is what a life I love looks like right now.
Community as a Catalyst for Growth
What role has community played in your leadership development and career path?
Community has been everything. When I look back at different stages of my life and career, I see how important it has been to surround myself with the right people. You really are the sum of the people you spend time with.
I thrive when I am around others doing great things, whether it is similar to what I am doing or something completely different. I love learning from people and celebrating their successes. Leadership grows when you surround yourself with the right people and does not diminish when someone else succeeds.
I have always viewed community as both inspiration and accountability. Whatever you are doing in life, having accountability is key. The community you have created is phenomenal. It brings together incredible people, allows them to connect, collaborate, and cheer each other on.
I believe deeply in collaboration over competition. You gain so much when you put yourself in environments where you can truly be part of something.
A Legacy of How People Feel
When you think of your legacy, what do you want it to be?
I want my legacy to be about how I made people feel. For me, it is about the impression I leave, how others feel when they are in my presence or after interacting with me.
That shows up in many ways. Lately, I have been focusing more on that because it is easy to put on your best self publicly, then come home and relax, and sometimes the people who matter most do not get the best version of you. I have been refocusing on how I can make my children, my husband, my colleagues, and even strangers feel seen and appreciated. That is what matters most, how people feel after being around me.
Advice for Women Learning to Pivot
What advice would you give to younger women who are building their habits and leadership, or to your younger self?
It might be the same advice for both. I would tell younger women that we are conditioned to believe success means going to school, getting a good job, and working for forty years. That was my plan too. But being willing to pivot when needed, and giving yourself the grace to do so, is so important.
That does not mean changing direction every year when you are unhappy, but rather being intentional about staying on the right path because only you can course-correct your own life.
I think back to my first major pivot, when I was traveling constantly for a retailer. I had an “aha” moment one winter day in upstate New York. My kids were little, it was a blizzard, and I had just landed, exhausted, about to drive a smoky rental car down icy roads. I thought, “What am I doing here? For one meeting? Why?”
It was my breaking point. I had a great job and worked for a great company, but I knew I needed to realign my priorities. I gave myself grace, rolled up my sleeves, and figured out what was next. I spent the next decade doing work I loved and building a life that came from that pivot, until it was time to pivot again.
That is the key. Give yourself permission to make changes in your career or life when something no longer serves you. That is how you keep growing.
About Jaime Lynn Curley
Jaime Lynn Curley is a connector, storyteller, and catalyst for growth who has built her life and career around helping others create what feels tailor made for them. A former fashion retailer turned entrepreneur, she’s led communities of thousands, built brands from the ground up, and learned that true success comes from alignment, not achievement. As a mom to three daughters, she’s modeled how to listen when life whispers “this isn’t it” — and to have the courage to pivot toward alignment. More recently, she’s made a meaningful career pivot that’s reignited her passion for connection— continually redefining success as something tailor made, built on authenticity, connection, and joy.
