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Author Stephanie May Wilson On Why & How We Need To Redefine Success Now

An Interview with Karen Mangia

Before we can make a decision of our own, we have to figure out what we think we’re supposed to do, and why. We need to quiet the outside voices, wherever they came from, before we have even a prayer of hearing our own. We must stop and examine the expectations we’re living under — pulling at each thread until we find the origin.

As a part of this series, I had the pleasure of interviewing Stephanie May Wilson.

Stephanie May Wilson is an author, a podcaster, a speaker, and the go-to guide for 20- and 30-something women as they navigate their most important relationships. Through her books, her courses, and her chart-topping podcast, Girls Night with Stephanie May Wilson, she has mentored more than a million women as they cultivate healthy, thriving relationships with God, their friends, their significant others, and with themselves.

Stephanie got her start as a writer when she packed up her backpack and traveled around the world for a year, keeping a blog of all her adventures. Stephanie’s writing has been featured on NBC, the Anthropologie blog, and in Relevant Magazine. She has also been a long-time blog contributor for CNBC’s Nightly Business Report, Darling magazine, and Christian Mingle.

When she’s not writing, speaking, or recording a podcast episode, you can find Stephanie laughing with her husband Carl and their twin toddlers, eating pizza with her close tribe of girlfriends, or planning her family’s big move to Spain.

Thank you for making time to visit with us about the topic of our time. Our readers would like to get to know you a bit better. Can you please tell us about one or two life experiences that most shaped who you are today?

My husband and I met working on the marketing team for a large non-profit organization. At the time, we were both working on side projects that we wanted to be our full-time jobs at some point. We thought we were years away from ever taking the leap to working on our own. As we were dating, and getting engaged, and getting married, we thought it was best to keep our work lives as steady and solid as possible.

And then, three months before our wedding, we were both laid off from the non-profit.

Immediately, we scrambled to try to find something else — anything else — that could keep us afloat as we started our new lives together. We both looked for another “real” job, a job working for an established organization. That seemed like the responsible thing to do.

We weren’t able to find traditional jobs, but we did both find jobs working for other people. I was a writing assistant and my husband, Carl, created a marketing through a partnership with the husband of the woman I was working for.

We felt like we’d not only found something stable, but we found something we liked and something that would get us closer to our eventual goals of working for ourselves and owning our own companies. (Me, as an author, him, opening up a branding agency).

But then, just six months later, it all came crashing down. We were laid off again — four jobs were lost between us before our first year of marriage.

We were embarrassed, confused and angry. We knew that none of the layoffs were exactly our fault. We hadn’t been fired. But still, we were the common denominator here, and we just could not seem to make this work!

So finally, after both cleaning out our desks a second time, we decided we might as well try to do our own thing — we had nothing to lose.

That was 10 years ago, and while I wasn’t at the time, today, I’m so grateful for those experiences. That turbulence at the beginning of our marriage made us such a strong team — a strength that’s served us over and over again through the last 10 years of marriage.

It also taught us the hard lesson that the safe choice isn’t always that safe, which means the risky choice isn’t always that much riskier. We learned that we could get the most traditional job in the world, and that still wouldn’t guarantee security and stability. I’m so glad we took the risky route because that turned out to be the best for us. It’s what we really wanted to do, and I’m so glad we didn’t let a false sense of security — or risk — hold us back from doing it.

We all have myths and misconceptions about success. What are some myths or misconceptions that you used to believe?

For years, I thought that more was more and bigger was better. But in the last few years, I’ve been realizing that’s not the case — not for everybody, anyway.

I’ve spent the last 10 years professionally growing my business and growing my team, while personally growing my lifestyle by moving into bigger and bigger houses. And then finally, about a year ago, my husband and I looked at each other — utterly exhausted from keeping up with it all — and said, “What are we doing?”

We kept adding and adding and adding to our lives, thinking that adding to our lives would add to our lives! But in reality, having more meant we had to take care of more. More stuff meant more work. A bigger team meant bigger expenses (and didn’t always mean more profit). We were trudging through life so weighed down by all the things we had to remember and take care of and organize and manage, that our lives were less free, less joyful, and less fulfilling than they had been before all of that adding.

So we’ve started subtracting.

We’ve both paired down our teams and paired back our expenses — both personally and professionally. We moved out of our dream home and rented it out to a different family — decreasing the amount of space we had to take care of and increasing our income in one big move.

And in just a few months, we’re going to be packing up our laptops and our twin toddlers and moving to Spain for a while — living with less so we can live so much more.

Bigger isn’t always better — sometimes going smaller is the key to where we want to be.

How has your definition of success changed?

As I mentioned before, I thought that more was more and bigger was better, but I just don’t think that’s the case. Everyone has a different capacity, different goals, different things they enjoy, different financial needs.

If time is at a premium and money is less valuable, then a job that pays less but requires less of you as a result is infinitely more valuable than a high-paying job that costs you every minute you’ve got.

I recently heard an interview with a woman who scaled her business quickly over the last few years. She did all the things she saw everyone else doing — added all of the products, offerings, different content channels, added team members, and she did it really well.

But after a few years, she realized that despite all of the success, she was miserable. She’d started this business to do something she loved, but because it had gotten so big and because she’d been doing what all of these other people told her she was supposed to be doing, she ended up with a big, successful business that looked nothing like her. That big, successful business ended up costing her all of the freedom and creativity she’d set out to find in the first place.

I’m learning that it’s essential for us to define success for ourselves — and to do it again and again in different seasons of life — before we try to chase it. Otherwise, we might end up chasing someone else’s definition of success and be disappointed with what our life looks like once we catch it.

The pandemic, in many ways, was a time of collective self-reflection. What changes do you believe we need to make as a society to access success post pandemic?

We need access to affordable childcare. I became a mom during the pandemic. My twins were born in November 2020 — right in the thick of it.

For a while, I thought if I just optimized my schedule enough, worked smart enough, and traded off throughout the day with my husband, we’d both be able to work full-time and also take care of our babies with only a little outside help. (At least for a while!)

The first day I tried to go back to work — and by that, I mean to do just a tiny bit of work for the first time in months — I was so excited to get back to it. We put the babies down for a nap, my husband Carl went downstairs to take a call with a client, and I went to the bathroom, refilled my coffee, sat down at my computer, and wrote one single paragraph before . . . both babies woke up.

I knew Carl was on an important call and that I needed to at least try to keep the girls somewhat quiet. But picking up and soothing two tiny babies at the same time is remarkably difficult when you only have two arms. So, trying a new tactic, I put the girls on the floor and crouched down over them, wrapping my arms around both of them, shushing them as they wailed, and wailing myself as I counted the minutes until Carl got off of his phone call. Forty-five minutes later, he sprinted up the stairs and found me and the babies lying on the floor together — all three of us still crying.

Yeah . . . this wasn’t going to work.

I’d spent my whole life believing (or maybe just really hoping) that it was possible to do it all — to have a great career and be a great mom — and I still believe it is. But now I know that it’s not possible without help.

But finding help is so much easier said than done. It turns out, finding a great babysitter isn’t like ordering a pizza. You don’t just call for help and have it in thirty minutes or less. It took months of searching, and interviews, and calling for references, and getting ghosted — only to start all over again — before we found someone we liked.

Daycare wasn’t any easier. I called around to try to find space for our girls, only to discover that I should have been on a waiting list the second I found out I was pregnant — and even that would have been too late. It was going to be at least two years before we could get spots.

And then there was the question of paying for it. When you’re thinking about having kids, you know it’s going to be expensive, and you know that one of the most challenging expenses will be paying for college eventually. But what I didn’t expect was the fact that childcare (even part-time) was going to cost roughly the same as a year of in-state college tuition — without the eighteen years to save for it ahead of time.

I don’t know how Americans can be successful until parents have access to affordable, quality childcare. And with affordable, quality childcare being increasingly unavailable, I think many families in the U.S. are reaching a breaking point.

What do you see as the unexpected positives in the pandemic? We would love to hear a few of your stories or examples.

I’m grateful for the ways the uncertainty of the pandemic has helped us live a richer life today. Let me explain…

When you’re working toward something in life — any sort of success — it’s tricky to find the balance between what you want in the short term and what you want in the long term.

Dreams, goals, ambitions, and the best things in life often take sacrifice in the short term for the sake of the long term. But especially when you’re a successful, goal-oriented person, it’s easy to take that a step too far.

People used to work their whole lives in preparation for retirement. They would work forty years for the same company, then retire, receive a pension, buy a house in Florida, and play a lot of golf. That was the reward at the end of their long journey. A lot of people lived a life they didn’t love all that much so that eventually, they could live a life they did.

But many of us have seen that story fall apart, and not just during the pandemic.

I graduated from college during the height of the Great Recession. As I applied for my first job, I found myself competing against wildly overqualified people who were at the end of their careers. They were either about to retire or already retired, and they’d lost all their money in the recession — so there they were, starting over, going back to work, and competing with twenty-two-year-olds for entry-level positions.

I’ve watched wonderful, wise adults lose all their retirement savings in a heartbeat after working their whole lives, and that’s not something you just get over.

I’ve also seen people we love have their health taken away from them much too early. They have the funds to retire, but not the health to enjoy it.

Living through the pandemic was the final tipping point for me in a lot of ways. It solidified my belief that I don’t want to save all my enjoyment of life for the end — because sometimes, unexpected things happen along the way.

So in recent years, I’ve been working for more balance — focusing a little less on the long-term and a little more on the short-term — evening it out a little bit.

We’re all looking for answers about how to be successful now. Could you please share “5 Ways To Redefine Success Now?”

  1. Embrace Your Authority

You are, without a doubt, the most influential person in your life. You are in charge. The calls are yours to make. Not only do you have authority over your life, but if you want to create a life successful (remember, we are redefining success) and enjoyable life, you’re going to have to start making some decisions — and making them now. If you don’t intentionally figure out what’s important to you and make choices accordingly, life and time and other people will choose for you. Maybe you’ll still end up somewhere you want to be. But approaching life this way is like throwing a dart with your eyes closed. If you hit the bull’s-eye, it’s because you were uncommonly lucky. It’s much more likely that you’ll end up with regrets.

If you don’t make decisions now, you might find yourself stuck in indecision for so long that you never build a life at all. The inertia that comes with not knowing what you want may cause you to miss your chance to build it. And while life sometimes offers us extra time and second chances, some opportunities may only be available to you in this season. If you don’t take them now, you might not ever get to.

There are other areas of life that work like an investment account or a fine wine — they grow, mature, and get better with time. You can wait and get started on these things further down the road if you want to, but there’s a lot to be gained if you start early.

The biggest risk of all is that you might end up living a life you never actually wanted. You might find yourself shuffled along through the years, guided by what other people say you should do without ever stopping to take inventory of where you want to go and what you need to do to get there. You might successfully build a life that looks nothing like you and doesn’t feel anything like you hoped it would. You might end up living out someone else’s dream instead of your own.

Here’s the truth: Very few people accidentally stumble into a life they love. If you want to build a successful life, you need to do it on purpose. You need to figure out where you want to go and start taking steps in that direction, but where you go and how you go about getting there is up to you. There’s a lot of room for creativity.

2. Remember that there’s not one right way to live a life.

This is something I talk about a lot in my new book, Create a Life You Love.

I say, “A beautiful life isn’t one-size-fits-all. You don’t have to forfeit things that are good and true about you in an attempt to squeeze yourself into a life you don’t actually want to live. You get to decide. You get to figure out who you are, what makes you you, and then be you with your whole heart — building a life you’re excited about and proud of, a life that looks and feels like you.”

Now, this is tricky because even the most independent thinkers among us still feel the pull of historical precedent and societal expectations. Even if you decide that you don’t want to get married, or have kids, or have a traditional 9–5, or buy a house — you’re likely going to spend years answering questions about your unconventional choices yourself to relatives like Aunt Sharon over Thanksgiving dinner.

You might even have people who look at your life and tell you that you’re flat-out doing it wrong.

But here’s a hard truth. Just because people have strong opinions about the right way to live a life doesn’t mean they’re right. It doesn’t mean their way is the only way, and it doesn’t mean it’s the only way (or the right way) for you.

We grow up thinking that life is a puzzle, with a right and a wrong way to put the pieces together. But the truth is, our adult lives aren’t puzzles to complete. They’re collages to create.

And here’s the best news: Once you realize there’s not one right answer and therefore no wrong answer, making decisions about your life can be an incredibly beautiful, fun, and exciting process, as you create a masterpiece and a life that’s all your own.

3. Examine your expectations

When we come to a fork in the road in our lives, we never show up empty-handed. We show up carrying societal expectations, expectations based on what our family has always told us we’re supposed to do, expectations we formed because of what we saw our friends doing, or even expectations we internalized because of a passing comment someone made one time that somehow just stuck. Even if we don’t ask for anyone else’s input, we still have it. We somehow know on a deep, cellular level what different people think we should do.

We have to figure out who we’re listening to, because only then can we examine the source of our expectations and decide if they’re actually what we want, or if we just think we’re supposed to want them. Let’s start by identifying your outside voices, figuring out what they’re saying and who’s saying it, and taking a look at what they’re telling you to do.

There are three types of expectations I’ve identified as I’ve been walking through, and then writing about the most decision-heavy decade of our lives (between our 20s and 30s) — what I like to call “The Everything Era.”

Those three types are:

  1. Explicit Expectations: These are expectations that have been directly given to you, either once or repeatedly as you were growing up: You will go to college. Everyone in our family has studied medicine and you will too. When you take over the family business . . . I never got to stay at home with my kids, so I want you to be able to.
  2. Implicit Expectations: The word “implicit” feels particularly poignant here because it means “implied although not plainly expressed,” and it can also mean “without qualification or question; absolute.” Those definitions perfectly capture the slippery nature of the implicit expectations we all face. Nobody has told us that we have to do things this way, but they don’t have to. We know what’s expected of us — and the expectation is absolute.
  3. Assumed Expectations: Assumed expectations are sneakier than the other two categories, but they’re no less powerful. Assumed expectations are expectations that nobody in your life directly puts on you, either explicitly or implicitly, but you carry the weight of them anyway. You assume other people expect these things from you, often because you’ve internalized the expectations that have been placed on other people.

Before we can make a decision of our own, we have to figure out what we think we’re supposed to do, and why. We need to quiet the outside voices, wherever they came from, before we have even a prayer of hearing our own. We must stop and examine the expectations we’re living under — pulling at each thread until we find the origin.

4. Who told me it has to be this way?

Sometimes I’ve been living under an expectation for so long, I am honestly not sure. Do I have to do it this way? I think so . . . right? Don’t I?

To figure out if an expectation is one I need to meet, I find it helpful to tease it out a little bit. A question I often start with is, “Who told me it had to be this way?” It’s important to cite our sources!

Once you’ve answered that question, examine the source. Who is this person? Is it someone close to you or someone on the fringe of your circle? Do you trust them? Is it someone who deeply knows you and your circumstances and all the facts, or someone making a casual comment that just happened to hit home?

Asking the “who” question is a crucial step. Who told you this was true or that it had to be this way? Is it someone you know and trust? Is it someone who was trying to give you thoughtful, intentional advice? Is it someone who knows what they’re talking about?

Unless we pause and ask these questions every so often, we could find ourselves making big life decisions based on the advice of a person we don’t even really know.

5. Gather some new inspiration

Now that we’ve liberated ourselves from the cacophony of unhelpful voices in our lives, it’s time to figure out what you actually want — to define success for yourself.

This can be hard. Have you ever had someone ask you what you want for your birthday and your mind instantly goes blank? You knew the answer right before they asked the question, but now that you’re on the spot, you’re frozen.

Knowing what you want in life can be this way too.

It’s great to be reminded (or have the first-time realization) that you don’t have to want something you always thought you had to want. But that just tells you what your destination isn’t. It doesn’t tell you anything about what it is.

So how do you figure out what you want in life? Yowza. You’re going to need a minute. You might also need some inspiration.

In my book, we take a look back through the last 200+ years of history — particularly at what women were expected to do. Women entered the workforce in droves in the 1970s, but for a long time, their career choices were limited. What if a woman didn’t want to be a nurse or a teacher or a secretary? What if she wanted to be an astronaut or an entrepreneur or an acupuncturist or an artist? It’s hard to paint with colors you don’t know exist, so if the people around you all seem to be following the same few paths, it’s going to take a massive amount of creativity to both imagine and engineer a future you have no context for.

This is one of the (many!) reasons why representation is important. It’s hard to be what you’ve never seen. So, for our last step, let’s talk about finding some inspiration.

Before you figure out what you want to do, let’s take some time to look at ideas for what you could do. Go wide with this. Seek out as many ways of doing life as possible. All the options certainly aren’t going to fit you, but broadening your horizons proves to you that there’s not one right way. It also helps you get more creative by giving you new pieces to play with.

You can do this by watching other people make decisions about their lives — watching their process, their choices, the outcomes. Seek out as many different examples as you can find.

Examples of different ways of living open our eyes to new possibilities, broadening our horizons of what could be. And even if we don’t see ideas we’d like to borrow for our own lives, seeing people live differently proves to us that there’s not one right way to live a life. It gives us permission to dream bigger, to dream differently. And that makes all the difference.

Over the years, I’ve spent more and more time looking for individuals who are breaking the mold — creating lives that look like them and feel like them and work for them. And the more I see, the more I notice, the more empowered I feel to create my own life in a way that’s a little different, a little outside the lines, but that looks like me, feels like me, and works for me and my family.

There’s not one right way to live a life. Success is not one-size-fits-all. But, if you are going to achieve your version of success, you first need to know what that is.

I’ve spent the last 10 years defining success for myself and building my life accordingly. And now, knowing how hard that was to figure out, I’m on a mission to help other people do the same …

Not build a life that looks like mine, but build a life that looks like THEM. And that’s what my new book, Create A Life You Love, is all about.

How would our lives improve if we changed our definition of success?

We’d actually have the opportunity to achieve it.

What’s the biggest obstacle that stands in the way of our redefined success? And what advice would you offer about overcoming those obstacles?

It’s scary to be responsible for our lives. We’re not sure if we’re strong enough, tough enough, or smart enough to wield that kind of authority. Maybe we’re ready to pay for our own car insurance, but we don’t know if we’re ready to sit in the driver’s seat for our major life decisions (and there’s no way we’re going off-roading). And that’s one reason we sometimes hand our authority over to others or delay taking it in the first place.

Another reason we might shrink away from making certain life decisions is fear of what we may lose if we do — the respect of our parents, a certain role in our friend group, or a position at our religious institution. If we’re eliminating options out of fear of what others will think, we’ve ultimately decided we’re not in authority over our lives. They are.

I understand this struggle. I’m the queen of the peacemakers, the people pleasers, the appeasers — and that’s putting it lightly. But after years in therapy learning about boundaries and how to practice them, here’s what I know:

You do have authority over your life. What you decide to do and how you decide to do it are both within your realm of control. You can give that control over to someone else, but make no mistake, you’re giving it away. Except for extreme situations (usually involving abuse of some kind), another person cannot take your authority from you.

So, what you decide to do, that part is up to you. What happens next isn’t.

If someone decides to distance themselves from you, exclude you, or even punish you in some way because you’ve made a certain decision, that is up to them. That’s the decision they’re making, and there may not be a whole lot you can do about it.

But you didn’t cause their reaction by making your decision — they chose it.

They could have chosen to respect your authority over your own life, to trust your insight and your boundaries, to support you in doing what you believe is good and right and best for you — even if they disagree with or don’t understand some of your choices. That’s what we hope the people closest to us do. That’s what they do if they’re healthy individuals who love us and who are for us. That’s what people do if they’re truly on our side.

We want our friends, communities, teams, and families to value our voices, care about our needs, and support our dreams. Having opinions — having hopes and dreams and desires and goals for our lives — is not a problem, it’s a good thing. If the thing our inner circle values most about us is our silence and our obedience — that’s a problem.

Where do you go to look for inspiration and information about how to redefine success?

One of my favorite ways to get inspired is to observe how differently people use their homes. Admittedly, I watch more than my fair share of home design shows, but I just love them. I especially love the shows about people living in crazy, wild, out-of-the-box homes — like a retrofitted firehouse, a tree house, or a super-narrow home on a tiny plot of land in the middle of a big city. These people’s creativity endlessly inspires me. Not only do they give me ideas I never would have thought of on my own for how to structure and design my physical space, but they give me ideas for other areas of my life too. When I see someone take something and transform it into something else, it helps me see that as an option for any obstacle or decision I’m facing.

Whether I’m on the internet, watching TV, out in the world, or talking to a friend, I’m constantly on the lookout for ways women are making life work for themselves. The more ideas and variety I see, the more creative I’m able to get in my own life and the more personalized I’m able to make my decisions.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US, with whom you would love to have a private breakfast or lunch, and why? He, she or they might just see this if we tag them.

Reese Witherspoon! She’s an incredible entrepreneur, thought leader, and champion for women’s stories. I love her work and I’d be honored to connect with her.

How can our readers further follow your work online? is my home on the internet. That’s where you can find everything I’m up to — my books, my courses, my podcast, my blog, and all of my social media links. If you’re a podcast person, definitely come check out what we have going on at Girls Night. We have such an incredible community of listeners.

And then really, the thing I’m most excited about right now is my forthcoming book, Create A Life You Love: How to Quiet Outside Voices So You Can Finally Hear Your Own. It’s a guided journey of self-discovery, helping women in their 20s and 30s (ish!) take the pressure off what they think their lives are supposed to look like by now and intentionally, confidently, and authentically build the life they actually want to live.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this. We wish you continued success and good health.

Thank you so much for having me!

About The Interviewer: Karen Mangia is one of the most sought-after keynote speakers in the world, sharing her thought leadership with over 10,000 organizations during the course of her career. As Vice President of Customer and Market Insights at Salesforce, she helps individuals and organizations define, design and deliver the future. Discover her proven strategies to access your own success in her fourth book Success from Anywhere and by connecting with her on LinkedIn and Twitter.

Author Stephanie May Wilson On Why & How We Need To Redefine Success Now was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.