It's was a great pleasure and honor for MOM.CEO to sit down (virtually) with Jan Singer who is one of America's most experienced fashion retail CEOs. She's built a reputation and a playbook for effectiveness and agility through her CEO roles at Spanx, Victoria's Secret, and J.Crew.
In our interview, we got to know Jan Singer as not only a business icon, but also as a mother, wife, and daughter.
Luc Chenier: The word NO is a powerful word in business, but how does its meaning work in your home, or is YES the preferred option?
Jan Singer: I always try and balance both NO and YES and a lot of MAYBES. A lot of “I think maybe?” or “That’s interesting, let’s see/let’s talk about it” versus a hard YES or a hard NO. At work, I don’t believe a hard NO is ever a good idea as a first conversation. It should actually come from a WHY place like curiosity, tell me more, and what are they really trying to mean or suggest. When you start from NO, you really kill everything such as innovation, exploration, spirit, etc.
Now at home, having twins that are now 13 years old, it sometimes has to be just NO!
It's the same with YES! Sometimes you just have to be willing to jump off that cliff with your team. In the end, it’s their decisions and they have to be accountable, and leaving everything up to me alone doesn’t allow for any empowerment. Therefore, YES and NO mean different things at work versus at home, and a lot of MAYBES and WHY’s can go a long way to making better decisions.
Luc Chenier: How do you want to look back and be remembered as a MOM and a CEO?
Jan Singer: I would like to be remembered for how people felt such as being empowered and coming to work with a purpose, being respected, felt heard – Not every day everyone feels that way, but for the most part. But yes, I also want to be remembered for putting up some great results as well.
Luc Chenier: And how about as a mother?
Jan Singer: I think you want to be remembered as someone who loved them more than anybody in the world. You want them to remember you as someone who was unconditionally there for them that taught and helped them a great deal about life and delivered a huge amount of unconditional love at all times. 
Jan Singer with her husband and the twins
Luc Chenier: They say with each generation, we should improve on certain aspects of how our parents raised us. What do you believe is your improvement(s) and what should be the improvement that your kids should implement from yourself?
Jan Singer: It’s so interesting because this morning I was listening to a Podcast on the subject of the next generation of kids (our kids) are the first generation who are economically far behind as to where we were to our parents. It's going to be interesting to assess the dynamic shift as time goes on. But emotionally for me, I think my mom in an effort to protect us from any form of pain or suffering if you can imagine as any mother would, her constant protection was always about NO and ‘bubble wrapping’ us to protect us from disappointment.
“You may not make the team. You may not get the job. It may not happen.”
As a parent, it’s a very protective way to ensure your kids are prepared. But as a child, you read that as “You don’t believe in me”. So, I think what I try and do is to protect my children in other ways and that sometimes means not protecting them! If they fail, fall down, etc. then so be it and they have to learn to get up and move forward. So, I think my mother was very afraid, not a risk-taker. She was afraid for me at every step and refused to believe that I had this level of a job up until recently because it scared her. “What if you lose the job?” she would say. “It’s ok mom. If it happens, then I’ll recover”. While I’m not young anymore, she still worries every day about me and her protection mechanism was a lot of ‘Don’t be disappointed if you don’t get it’.
My dad is still working at 85-year-old and about to finally retire. I would say that I am taking more enjoyment out of my life than he took the time to do. He worked hard and provided so well for our family, but I feel he lost a lot of time with life.
Luc Chenier: How will your kids improve on you with their kids?
Jan Singer: There so young that I’m not sure yet what my issues are. My husband and I had kids later and I am closing in on to the arch of my life, whereas my parent had us in their early 20s. So, where my parents were with me and their maturity level is quite different from where I am with my children. I’m sure there will be a lot of issues as they tell me often what I should do better. When I will get to look back, it will be interesting as David and I are at different points in our careers and have different resources, perspectives, and with age comes wisdom, etc. I am not sure what the improvements should be at this time, but I’m sure if you were to ask my kids, they would give you a detailed list today!
Luc Chenier: What top 3 lessons did your parents or a mentor give you that you feel is very relevant in today’s digitally connected world?
Jan Singer: There are many things. First of all, work is hard and hard work is important. There is no replacement for hard work!
“The work ethic in my house was very strong.”
We come from a blue-collar industrial city and 4th generation where everything was about hard work, family, and always winning! I went to high-school with 6,000 students and you needed to find a way to survive. So, work is hard and there is no replacement for hard work.
Secondly, my mother would tell me that it might take time, but the cream always rises to the top. It can take its time or be quick, but the cream always rises to the top and you simply need to be focused and patient.
The world is truly small. I’m not sure if they taught me this, but I believe that it’s an extremely small and round world that we live in, so be kind to others because everything comes back. Like the fact that you contacted me Luc, and that we don’t really know each other, but you have been in contact with many people/friends that I am connected with, there is no doubt that when you’re out in the universe and participating, the world becomes incredibly small and round. So be kind to each other.
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Jan Singer and her family attending the Outstanding Mother Awards
Luc Chenier: What did you sacrifice (and maybe still are) in order to balance being a CEO while raising children?
Jan Singer: I think you first have to sacrifice the notion of balance. There is no such thing even by definition – ‘two opposing things that are heavy that you are trying to weigh'. It’s a super set-up for failure. I believe the first thing you have to get rid of is perfectionism. When you living alone, single, and working then you can manage things exactly the way you want them to work, then you can aim for perfection. But when there are other people involved either in leading at work or being a mom, wife, or partner at home then you have to let go of perfection and go for progress. Moving forward is the key idea to aim for.
The sacrifice of striving for perfection has to be given up quickly and you realize over time as you are growing and getting promoted, and moving forward you are competing and trying to deliver results but you are hopefully doing that not at the expense of other people but you are doing that to advance the business. When you reach a certain level of leadership, the wisdom kicks in and you begin to make very strategic trade-offs every day and you have the wisdom and experience versus when you are younger you take risks where you can ‘Wing It’ and understand that most likely you can easily recover as the stakes are not that high, But, as we get older, we move into different levels of leadership and we make very thoughtful trade-offs that may or may not work. Overarching, I go for progress over perfection – so the sacrifice would be perfection.
Luc Chenier: Is Work/Life Balance realistic with the pandemic, isolation, work-from-home, virtual schooling, etc.? Was it ever a reality even before the pandemic?
Jan Singer: I think it’s a real joke and a set-up for failure when people are saying you have to find balance. In our email correspondence, we spoke if it was harder for women than men? I would have to say that by the nature of the numbers it’s much harder for women. A good example of this would be the last round of job numbers in the US, the impact was 100% on women.
"This is simply shocking and staggering, because its set-back is almost back to the ’80s for women in the work-force."
It’s not only women who lost their jobs, but more so women who were forced to opt-out because of the situation that we found ourselves in.
Maybe it’s temporary, but it’s still a major set-back which means fewer women are in the workplace, fewer women CEOs, and most importantly fewer women being on boards or being Chairman of the Board. Super important!
Melanie Hobson who is an amazing Chairman of the Board is rarety these days in having a woman chairing large scale or even small companies. So, by that fact, it’s harder because you don’t have a community of like-minded people around you where you can have access to wisdom and answers with potential solutions and resources, and even the right lawyers sometimes.
With all these issues and being a woman CEO and being asked to figure out what Work-Life Balance is I feel is simply crazy. The world we are living in now is pushing things to change. A good example would be this morning where I worked for a few hours and then had a break. The sun was out and it had snowed, so my son and I grabbed the inner-tube and our dog and went out sledding for a couple of hours. I ran up and down the hill and guess that counts as my daily work-out. Then I came back to have my interview with you and after I will jump in another meeting. So, is that Work-Life Balance? I think a deeper issue, is that there is now more than ever no separation between work and life versus balance at work and life.
Enjoying the sun and sledding for a few hours in between meetings with her son and the family dog
Luc Chenier: I was speaking not long ago with Jeff Hoffman who echoed what you are saying that the whole concept of Work-Life Balance is a myth. For him, Work-Life Balance is more about how do you react to the situation at work and home.
“There is no such thing as Work/Life Balance, especially when you are at our level in business. They don’t pay us to have a Work/Life Balance!”
Jan Singer: I think Work-Life Balance should be more about Work-Life Separation.
Luc Chenier: Do you feel that men have improved at being involved dad’s and are they now getting ‘exaggerated praise’ during the pandemic for what mothers have been doing on a daily basis without any recognition?
Jan Singer: First off, let’s make something clear. Fathers, Husbands, or Partners don’t ‘babysit!’ There’s no such term and it doesn’t exist because this is your child. I’m not really hearing anybody else getting better ‘grades’ because everybody is struggling. It’s really hard being isolated in your home for almost a year and leading a team over ZOOM through a pandemic, social injustice, crises, an election, and an insurgency, etc. These are incredibly hard times for anyone to lead. It’s interesting for me about the job’s numbers for all the reasons that we know such as restaurants, retail stores, etc. that the subordinate groups are impacted the most and that is truly unfortunate and a hard setback.
Being home so much now, I look at my kids and wonder if I had been home more often would that have been different? But I can’t criticize because I’m lucky that my husband is home and retired and that helps tremendously and I am so lucky at how amazing he is. Everyone is doing the best that they can and I do believe as I mentioned that it’s harder on women and on people without resources to fall back on. Just last night there was a major snowstorm in Austin, Texas where it never should snow, and the power grid shut down with temperatures at 15 degrees (F) and people don’t have the resources, money, or jobs & stimulus to survive. I fully understand that I’m not sitting in that ‘boat’ and I’m incredibly lucky. But, too many people are sitting in that boat and times are truly hard with many families suffering.
Luc Chenier: CEOs are tasked with setting and implementing business KPI’s, growth, and performance targets to name a few. Do you feel that as parents who are shaping the next generation of leaders, we should create plans of action in our homes?
Jan Singer: I’m married to a retired Coast Guard Commander and he would love nothing more than a 5-point plan on what we are doing, but I won't allow us to do this. I feel that when you sometimes try to figure it all out you kind of die. I don’t speak about my work when I come home as it’s too exhausting to relive and take others through the details of my day at work again. I think it’s very freeing to not have that level of structure at home. BUT! No structure is not the answer either. It’s probably good to find a certain balance that is somewhere between what is our family Mission, Vision, and Purpose, and mixed that with just ‘winging it’ every day is probably a better balance in my opinion. As a family, we do speak about it in sort of increments. When I was single I used to have a high need to know where are we going? What are we doing? Now I feel I need to have some knowledge but I also need time to just let the world reveal itself more on where it's going in order for us to make decisions with a lot of agility. Therefore, I don’t always have to know everything all the time as it makes me anxious at home, but at work, it’s the opposite. 
Singer family 'selfie'
Luc Chenier: Many CEOs have told us their biggest regret as parents were that they wish they could have been more 'in the moment' with their kids as opposed to still being at the office in their minds, on the phone, checking emails, etc. Does that ring true for you?
Jan Singer: I don’t know anybody who works and even those who are at home who think that they have done enough. I don’t think that anyone sits back and says:
“Wow! I really nailed raising that kid!”
You have to let go of that notion with what I like to call guilt which is really a useless emotion. I don’t like having any regrets and I do the best I can do. Of course, there are times I wish I was home or did not miss a recital or a game, etc. But now that we’re all home and I wish I were traveling a little bit to balance things out. I think that would be good for them as well. We recently went to Boston with my husband to help move my dad and I told my husband that the kids need us to be away for a couple of days. They needed this as 2 parents being home all the time and constantly asking them if their beds are done, if their homework completed, are the dishes made, and so on. If I were them, I would absorb myself into Minecraft or something else.
"Both kids and parents need their space."
There will always be things that you wished you could have done better and dwelling on that doesn’t make any sense and the inauthenticity that your kids will sense about this will be incredibly clear to them.
A good example of that is a woman who I knew from a few boards we shared together whose daughter was present said: “Remember mom that time you stopped working and came to PTA and to all my meetings? That was a disaster when you got involved with my school! I hated when you did that!” I asked her why and she said it simply wasn’t who she was and more so the mother was not happy either.
Of course, I wish I could have done better, but I don’t dwell and I don’t think the kids do either. What you focus on can become bigger, so focus only on the good.
Luc Chenier: What advice would you give for being a successful MOM.CEO?
Jan Singer: My first tip would be that everything in the middle of the night seems bigger than it really is and has an odd sense of distortion.
"Wait till the morning before making any decisions or actions."
Don’t send an email, write a text, go on social media, etc. If you can’t sleep, then do something like watch a movie or read a book, but don’t dwell on something because it always seems much bigger at 04:00 in the morning.
Another thing is that growth is not as linear as it used to be where you used to climb a corporate ladder. The world doesn’t work that way. You have to work as a collective and lean on each other. It takes a collective mindset to move the ball forward. The way the workforce is structured requires more heart than simply using your head and definitely requires much more empathy and leadership to bring connectivity, etc. Focus on these things when situations get hard such as people wanting to muscle the answer of solving a problem or finding a quick solution. You need to pull-out and make sure that the team is connected and feeling good so they can get to the answer. You don’t need to rush things. And when in doubt, don’t make a decision.
"If everyone is stuck, then make the call, own it, and move on."
Don’t let it get to a point of crisis. You will need to make the call and make it in a way that people feel part of the process, or at least somewhat bought-in.
With all the issues we are now facing these days, the most important is to stay connected to your team as much as you can and the most important for them is to really understand where they’re at emotionally. This is probably the darkest winter of our lives where it's cold and snowstorms in the south and across the world where it should not be happening. We're still deep into ZOOM, still not traveling, we have a vaccine-ish, etc.
Staying connected to other CEOs is key to finding new solutions
So, getting creative and connecting to other CEOs on how they deal with is a great strategy for finding new solutions. I have a couple of nights a month where it’s just women CEOs on a call where we just talk about whatever the topic of the week is. It can be anything from how we plan to reopen when the vaccine rolls-out. Those are just great conversations to have in order to stay connected so we can then shift and face our teams and recreate that environment for them to get connected even that means on ZOOM.
Luc Chenier: Is there a famous quote that best describes you and your approach to life?
Jan Singer: One of my favorites I think is from Dr. Maya Angelou who said:
“When we know better, we do better.”
I believe that speaks well to my curiosity about Why? Why? Why? The reason for this is when I have the information I can think more clearly and see around corners and can make decisions better to help my team.
I always tell my team that I am really good with good news and also great with bad news. But no news is not good for me. So, when we know better, we do better is truly important for me. It also speaks to being ok for it being what it is at this moment because NOW YOU KNOW! You don’t have to beat yourself up about things no being perfect. Now you have more wisdom and you can go and build on that.
Luc Chenier: Any last words of wisdom?
Jan Singer: I think it’s important to know that in my career I’ve had great successes and I’m not done. But the more you get into senior leadership roles, the higher probability of change will happen. Tenures have become much shorter, and the marketplace is even more volatile with much higher stakes, etc. I hear a lot of women being afraid of losing their jobs and panicking. I ask them what is the worse thing that can happen?
“I’ll lose my job, then I’ll be homeless!”
No, you won’t! It’s a far leap from where you are now. But we have these irrational fears as moms that these are the worse things that can happen. But we forget that we are extremely resourceful humans. The truth is that the higher up you go, it's highly likely that you will lose your job. It’s not an IF?, it's more like a WHEN! 
Illustration of Jan during her tenure as CEO of Victoria's Secret
A good example of that is a woman I know who was the first digital editor, producer, and leader of a major network in news. She was in a highly concentrated men’s business environment where being digital was directly competing with the traditional news source. She was facing some stiff competition and feeling the hard push-back towards what she was doing. She naturally panicked and told me that was afraid she would lose her job. I told her she most likely would and that she needed to start wrapping her head around this reality and how she would react, adapt, and get comfortable with that and move past it. She looked at me with such horror.
The next call I received from her what that she had won an Emmy Award and she would go on to win 3 more Emmy’s and an Edward R. Morrow Award. She is an amazing leader and digital reporter. She then lost her job. Things like this happen all the time. She called me and said: “You’re not going to believe what just happened to me?!" And she kind of sounds a bit excited, to be honest. “You told me this would happen and it happened!”
The wisdom is knowing this will happen and starting to think about what that means and looks like when it does happen and how to get comfortable in that space. That is when actually really incredible things happen. Holding onto what you have for dear life is not what growth produces. Being willing to let go of what you have or having someone telling you you’re done and thanking you for your services is when opportunities start happening. I will always believe that and I will never stop believing in that! I’m a product of that I am happy about this fact.
The wisdom is to not be afraid and take the risks, win the award or not. Keep your job or not. But be integral, be your word and be a multiplier of ideas and at the end of the day when you look back when you’re at my dad’s age, chances are you will feel pretty good at the run/life you've had rather than holding on for dear life as that is when bad things happen. 
Enjoying life and appreciating the little moments with her husband David.
Luc Chenier: Jan, thanks for sitting down and having such an open and honest talk from one DAD.CEO to a MOM.CEO. I’m a big fan of your work and I look forward to following your next adventures and I truly hope we can stay in touch.
Jan Singer: Please, let’s stay in touch Luc! And thank you from halfway across the world and thank you for starting this conversation because there are so many women that come to mind who will appreciate our talk and would also love to have a chat with you as well. So, thank you for continuing to shine the light on the moms who are leading in business.
ABOUT JAN SINGER
Photo Credit: John Aquino/WWD
From Secretary to CEO, Jan Singer has built a career advocating for consumers and empowering teams to deliver results in Consumer/Retail across Lingerie, Beauty, Sport, and Fashion. She believes in finding the highest potential in the people, the business, and the brands she leads.
Jan Singer was most recently the Chief Executive Officer of J.Crew where she led the teams through transformational work including, financial restructuring, value creation planning, acceleration of e-commerce, evolving brand positioning, and adding meaningful purpose. These workstreams kept J.Crew financially viable through this time of crisis and set-up the brand for future growth.
Prior, Jan was Chief Executive Officer for Victoria’s Secret Lingerie, the world’s most recognized intimate apparel company. As CEO, Jan was responsible for the more than $4 billion lingerie business, which included Victoria Sport. Jan built back key core categories and introduced the softer side of sexy by adding 300M sleep/lounge acceleration. Jan joined Victoria’s Secret in 2016 from her previous role as Chief Executive Officer of Spanx, Inc., a lingerie/lifestyle brand offering hosiery, intimate apparel, and swimwear, where she added innovation and actively grew the business, reaching new consumers and inspiring future leaders.
Prior to being a CEO, Jan spent a decade at Nike Inc., where she was Corporate Vice President of Global Apparel and Corporate Vice President of Global Footwear. While at Nike, Jan managed multi-billion dollar product engines, spanning product design, merchandising, sourcing/manufacturing, and innovation. Under her leadership, the team delivered industry-defining products and growth with programs like FlyKnit, Lunar, Waterless Dying, and uniforms for the NFL, World Cup, and the Olympics covering men, women, and kids globally.
Jan Singer with her team at Nike
Prior to Nike, Jan served as the Vice President/General Manager of Women’s at Reebok and held executive roles in luxury beauty for Prada, Calvin Klein, and CHANEL. Jan also served as the Beauty and Fitness Editorial Director for YM Magazine and was a freelance beauty and fitness writer.
Jan served as a Board Director for Kate Spade & Company from 2015 to 2017. In 2018, she was named a National Outstanding Mother honoree, an award honoring her contributions and influence as a mother, businesswoman, philanthropist, and mentor. Jan was also the 2018 recipient of the Beta Gamma Sigma Business Achievement Award, recognizing her significant accomplishments in business, leadership, and service.
