Wonderhell: Why Success Doesn’t Feel Like It Should and What to Do About It – A Conversation with Laura Gassner Otting

Wonderhell: Why Success Doesn't Feel Like It Should and What to Do About It – A Conversation with Laura Gassner Otting

Have you ever accomplished something you weren’t so sure you could do? Success has always been the end goal, but when you achieve it … something infuriatingly predictable happens. You start wondering what more you can do.

Instead of success bringing you happiness, it hands you an increased hunger to achieve something even bigger. And with that desire also comes uncertainty, self-doubt, anxiety and stress. Success, in other words, is ‘kinda’ wonderful … but it’s also ‘kinda’ hell. Welcome to Wonderhell! Wonderhell is that space in your psyche where the burden of your newly discovered potential plops down, unpacks its backpack, and asks: Hey, you! Whatcha got for me? Living in an ambitious, results-oriented society, we often mischaracterize the turbulent emotions that surround success, deeming them a “necessary evil”—a byproduct of one’s rise to the top. We tend to think that we just need to survive these difficult moments, to hang on by our fingernails and somehow get through these stressful, unwanted side effects of our success. We torture ourselves with a never-ending internal dialogue: I can handle this. Can I handle this?

But we are wrong. Learning to live in this newfound potential can be exciting rather than exhausting. Emotions like fear, anxiety, and heartbreak are not collateral damage, slings and arrows to be absorbed and swallowed down, silenced and pushed aside. Rather, each emotion is a portal that shows us what more we can do, if instead we recognize that on the other side of this wonderful hell that we so badly wanted is another and another and another . . .  but only if we choose to accept it.

Laura Gassner Otting is a frequent contributor to Good Morning America, the TODAY Show, Harvard Business Review, and Oprah Daily, Laura’s 30-year resume is defined by her entrepreneurial edge. She served as a Presidential Appointee in Bill Clinton’s White House, helping shape AmeriCorps; left a leadership role at respected national search firm to expand a tech start-up; and founded, ran, and sold her own global search firm, partnering with the full gamut of mission driven corporate and non-profit executives.

In this interview, I speak to Laura Gassner Otting. We discuss the true nature of success, why it isn’t always what we expect it to be, and what she’s learned from working with thousands of the world’s most successful executives about life in Wonderhell.

Q: What does success really mean?

[Laura Gassner Otting]: What are we really talking about and what we think we are talking about could be two different things because when we use the word success, the perception is that everything is about being bigger, better, faster, more etc..Success would mean having the fancy house, the luxury car, the right spouse, the clothes in exactly the right size. Whatever we have been handed externally and around us is the definition that we carry with us.

All of us at some point of our lives, whether it was a teacher or parent or boss or a celebrity, handed us a definition of success and said this is what matters. But they left out the most important that, which is this is what matters to me. It might not be what matters to you.

I spent 20 years in executive search, and I was hired by my clients to call ‘the most successful people’ in the world. Bold face names in bold face organisations.

It was my job to recruit them away on behalf of my clients-  it would sound difficult right? I would call super successful people and try to get them to do something different. However it wasn’t that hard, because despite all the success, which is why I was calling them, they were not very happy which is why they were calling me back.

I became fascinated about this question of why success doesn’t equal happiness. It came to the fact that we stopped thinking about what does success mean to us individually. Even if we did have a sense of this is what success felt like, the world changed. We changed. Our families changed. All sorts of things happened, and so we don’t stop and give ourselves an opportunity to redefine success at every age and every stage, for what success means to us.

Q:  Does success brings happiness?

[Laura Gassner Otting]: My first book Limitless is all about how to work out this definition of success for ourselves, and what I learned during the time of executive search, is that it’s not success we should be seeking but consonance, alignment, flow. When what we do actually matters to us. We are being called upon to solve a problem at hand, to use what we do best in the world, and in turn being rewarded for in a way that is meaningful to us.

Everything works when you are in consonance – when closing an important deal, making it rain, when you’re helping a friend or loved one through a hard situation in private and that’s your definition of success. But then, what if you find your definition of success, the thing that really matters to you, and you achieve it, it’s not done. It’s not finite. We think once we reach that level of success we would ‘I’ve made it!’  Easy money, everything’s great’, but it turns out here’s what I learned. Every time we achieve some version of success, whether you’ve sold that first company or maybe you’ve just sold your first tube of lipstick or your first consulting contract, every time we achieve some version of success we see another version of ourselves that we didn’t even know was possible. We as humans wonder what else potential we have to explore.

I didn’t know that it was available to me but now that it is, and that’s amazing and it’s exciting and it’s wonderful, it’s also anxiety provoking and stress inducing and identity questioning, because suddenly I feel the burden of that leaning on my shoulders.

Once you have for example sold your company and made millions and living the dream in a beautiful house with the perfect marriage, suddenly people ask  ‘what’s your legacy going to be?’ so now the burden is to figure out philanthropy. It’s about constantly finding ourselves and the success is really a portal into the next stage that we’re possibly capable of doing, and we have to decide how we’re going to face that tsunami of emotions that then comes flying at us when we thought all we were going to have was happiness.

Q: What created the concept of Wonderhell?

[Laura Gassner Otting]: Yes. I was on a red eye flight coming home from speaking at a conference on Limitless, where I opened for Malala which was amazing. I was thinking to myself  I can’t believe this is happening, this is wonderful. At the same time I’d never been so exhausted in my entire life so although it was exciting it was also kind of hell. It’s wonderhell.

I wrote, not thinking much about it on my social media about I don’t know where I am, but in a blur between the blur that was yesterday and the blur that will be tomorrow, is the space I’m in right now. The space I’m in right now is wonderhell. I  literally posted it on Facebook and my friends said ‘that’s a great word, I’m in wonderhell right now. You should buy that url. That should be your next book’, and it was full of comments as people clearly related to the concept of ‘wonderhell.

I didn’t do anything until when the pandemic hit I was still in this wonderhell space so I started talking to people, and interviewing them on my podcast. During this time, I noticed that themes emerged when you are in this embarrassment of riches – I have too many customers I don’t know what to do with, I suddenly have to create a structure to my business because I’ve grown so much, or I substituted in for my boss to do that presentation and maybe I want to be doing more presentations. All this was incredible to realise. I had a brand who said to me ‘You shouldn’t name your book wonderhell, nobody is going to buy a book they don’t know what the word on the front cover means’, and I replied, anybody who’s in wonderhell will know what that word means the second they see the word. So I’m glad that you said that.

Vikas: Wonderhell is almost like a post-traumatic stress zone of being.

[Laura Gassner Otting]:  Wonderhell can certainly be traumatic, but to address the first piece of it, I was talking about this idea of wonderhell. I am a very bad marathon runner but I’m persistent. I have more stubbornness than I have talent is what I will say. I am also a masters rower, also more stubborn than talented. In each of these, you’re racing against the clock. If I finish a marathon at 4.02 (which is the fastest I’ve ever ran a marathon in my life), what is the first thing that occurs to me? Oh that was so close to 3.59, I wonder if I could do it.  Then as soon as you imagine yourself crossing the line at 3.59 boom, you’re in wonderhell because everything that you do, every time that you run you’re like ‘if I could just keep that up for 25 more miles that could be 3.59’. So as soon as you see it, you can’t unsee it.

During my executive search, that was the main reason why internal candidates always left their roles because the process of interviewing for another job, you had to wear the clothes for that role, speak in the voice, solve problems in that role, and once you see yourself in that position you can’t unsee yourself. So it works in business, it works if you are an employee, an entrepreneur, it works in everything that we do in our lives. The burden of your potential I think is really universal to every part of our lives.

In terms of the PTSD piece of it, I think you’re really onto something with that because we could take it as this experience of it’s traumatic and I have to keep going and keep going and keep going. When the pandemic hit, like a lot of people I just stopped sleeping due to stress and I didn’t know what to do with myself.

I was trying to keep my business that is a go to events, fly to events to go speak on stages when there were no flights or events or stages.

I was trying to keep my business going and also trying to keep my teenagers and my husband and everybody alive and happy and safe. I went to see a psychiatrists and was like ‘I think there’s something wrong with my brain’. He diagnosed me fairly quickly as being a born overachiever. Born overachievement complex was my issue, and he said we can work on that.  I said overachievement? That’s a feature, not a bug. He’s like yeah but it’s not tenable. And I said no, no, I’m fine, I’m totally fine and he countered with the checkmate of ‘but you’re here’.

So this concept of wonderhell, the book is divided into three sections – imposter town, doubtsville and burn out city. In the beginning you feel like I’ve just gone to this next level, oh my god I don’t belong here, people are going to find me out.  Then you’re in doubtsville where you’re not sure because you’re making it up as you go along, and then there’s the do I keep going at this pace? For a lot of us, some of the ways that we deal with wonderhell is we say maybe I don’t want to keep growing, maybe the size I’m at right now is fine. Like, I see the potential that I have but maybe I can do that in 2 years or 5 years or maybe that’ll be with my next business or next product or maybe I have to bring on a business partner first. So I don’t think we have to continue to keep throwing ourselves at the floor and having those injuries when we have to stop and say well, is this what success looks like to me now? Am I just doing it because it’s the last thing I did? Am I doing it unintentionally, I just keep going, or do I want to say at this age and at this stage, what makes sense for me now?

[Vikas:  Self-doubt bit is really interesting and something which is really not discussed enough I think. Because even if somebody has the qualifications and has everything they need to do it, the minute you’re out there in the clean air having to go do it, self-doubt kicks in.]

[Laura Gassner Otting]:  100%. Self-doubt and everyone else’s doubt kicks in too. When I decided I was going to sell my search farm I would run into a friend at Starbucks and I would tell them I don’t know what I’m going to do next, and they’d be like oh my god, you can’t do that, that’s too scary. What they really meant was ‘I can’t do that, I’m too scared’.

But because they said that, it became this little cancerous nodule in my brain that just started to grow, and every time something went wrong I was like oh maybe this is too scary, maybe I shouldn’t have done this.

We have to think about who we have around us at every stage, and both in person but also studies show that the people who you are connected to online. For example if you have somebody you see all day every day on social media, they are going to influence your thinking about what your possibility is, and what your boundaries are and what your challenges are more than the people who live in the same house as you. We really have to think about who the inputs are, because the world is completely uncertain, and if you are doing something you’ve never done before there’s probably not a road map of how you’re going to do it.

There may be other people who have done similar things but they are not going to give you all the secrets, nor be available for you 24/7 so you have to get used to flying without a net and knowing that what got us here is pretty great, so if we’re able to be successful in this part of our life, maybe some of those things are not directly transferable but they can translate, the skills can translate instead. To summarise it is essential to think about who we have around us and the difference between those transferable skills and those translatable skills and having that confidence that success as you define it in one area of your life can apply to another area as well.

Q:  Are there any common characteristics that you found of the best people you’ve worked with?

[Laura Gassner Otting]:  When I read about interviewing all these people for wonderhell, I thought that they were going to be able to help me find a way out of wonderhell. I was like I’m going to find the solution! I’ve done all of the things, none of them worked. I’m finally going to figure this out.

After 100 conversations with Olympic medalists and glass ceiling shatterers and startup unicorns and everyday people like us, I’ve realised that you don’t find your way out of wonderhell, you just get comfortable being in it because on the other side of this wonderhell is simply the next one followed by the next one.

I taught a class in entrepreneurship once and at the back of the room a woman held up her hand at the end of the class, and she said ‘what would you do if you failed?’ so I said let me ask you, you’re in a class about entrepreneurship, you’re an entrepreneur, you’re presumably creating a business, what will you do if that business fails? She said oh I’ll just go get a job in a cubicle and figure out my next business. And I was like great, now you know what to do! What will you do if you succeed? And she couldn’t answer the question.

Finding somebody who ran Smith Barney but she was still feeling imposter syndrome about starting a $2 billion investment company, I was like well if she’s still got it the rest of us are screwed, what are we going to do? Here’s what I learned. The ones who were the best at it were very comfortable being uncomfortable. They said I don’t know what I’m doing, but I’m going to figure it out because I understand what the safety net is that I need. I know what plan B is – if I fail at this, I know what I’m going to do instead.

Q:  Do you think that mentorship is really important in wonderhell?  

[Laura Gassner Otting]:  Absolutely. If you’ve got imposter syndrome or doubt or uncertainty or anxiety, mentoring someone else is the best way to remind yourself on a regular basis that you know what the hell you’re doing!

I think mentoring is super important, I have to say, I’ve got more out of that mentoring relationship than I’ve given. I always learn more, I’ve found more, I’ve figured out especially as a writer how to tell a story, to teach a lesson in a way that’s me just saying it in my own brain. It literally allows me to figure out how I want to show up deliberately in the world, than just flying by the seat of my own pants on my own. If there is the post sadness when bowing out of a business I could write a 7 book series on the crisis of identity I had when I was no longer LGO, CEO, here’s my business card!

So sort of figuring out who we are, and that goes back to that first question of what does success mean? Does it mean I exited and made a ton of money? Does success mean I exited but I created an institution not a cathedral? Does success mean I exited and now I just have freedom to go onto the next thing? But thinking about what success is, if you’re finding success as defined by someone else, when you get it it’s going to be pretty hollow.

[Vikas: I feel as if a lot of individuals don’t create the space to figure what that is and indeed be honest with themselves about that. And I guess that links to stopping being people pleasers and pleasing ourselves part of this.]

[Laura Gassner Otting]: Yes, in Limitless I talk about this concept of consonance as I discussed earlier, being made up of 4 parts – calling, connection, contribution and control. So there’s so much pressure to ‘find your calling’. First of all I think it’s plural because we have different callings at different times in our lives, but also we have linked the word calling to purpose, and purpose to service, and service to sacrifice. Because if you’re not literally giving the shirt off your back to a poor kid in need you’re not sacrificing, you’re not serving, so clearly you’re just one of those people who makes a lot of money or you’re pushing papers all day long. If your purpose is to cure cancer, that’s amazing, but if your purpose is to make a lot of money so that your family doesn’t have to be in debt and make different decisions than you had to make, that’s great too. If your purpose is to make even more money and buy the beach house and a Maserati and maybe you want to donate money to that person who’s trying to cure cancer, great. But your purpose is your purpose, plain and simple.

At every age and at every stage reached we need different amounts of it, and I think a lot of times we are not defining that success for ourselves, it’s because somebody like a high school counsellor or a college counsellor gave us a definition and then we stuck with it. We picked a path, we picked a major, we picked a college, we made that decision before we had a frontal lobe. Literally before our brain was capable of making a good, sound, logical decision.

We have to stop purpose shaming everyone.  Maybe when you are young your purpose might be super idealistic, when you’re in the middle of your life it might be maximising your income, when you’re later in your life it may be mentoring and figuring out your legacy.

When my last book came out I did like 100 podcasts and more than a handful of times I got what I considered to be the dumbest question, which I don’t think you ask. But what advice would you give your 22 year old self and I was my 22 year old self who is listening to a podcast which was recorded over the internet and I’m listening to it on a cellphone? None of those things existed when I was 22, so even if I did know who I was at the time and knew what made me happy, the world around us changes so quickly. So I think it’s not just figuring out that definition, but it’s also knowing that every 7 years or so that definition is going to change, because we are going to change, our families are going to change and the world around us is going to change.

Q: What does legacy mean to you? What do you hope is the echo or imprint that you’re leaving on the world through your work? 

[Laura Gassner Otting]:  Simple answer. When I die, I want people to say my life was a little bit better because Laura was in it. I have no expectation to fix the climate crisis or save the whales. Wouldn’t it be great if I helped somebody find their purpose and they could do it? But that’s it, I just think we need to leave this place a little better than we found it and I hope that I have some active role in that with as many people as possible.

Thought Economics

About the Author

Vikas Shah MBE DL is an entrepreneur, investor & philanthropist. He is CEO of Swiscot Group alongside being a venture-investor in a number of businesses internationally. He is a Non-Executive Board Member of the UK Government’s Department for Business, Energy & Industrial Strategy and a Non-Executive Director of the Solicitors Regulation Authority. Vikas was awarded an MBE for Services to Business and the Economy in Her Majesty the Queen’s 2018 New Year’s Honours List and in 2021 became a Deputy Lieutenant of the Greater Manchester Lieutenancy. He is an Honorary Professor of Business at The Alliance Business School, University of Manchester and Visiting Professors at the MIT Sloan Lisbon MBA.