Nikki Webster: “Humor”

Humor — People are so disconnected from one another today and we’ve gotten way too serious. I have a very dry childish sense of humor that comes out in what I write. I think the world needs to lighten up a little, laugh a lot more. And stop assuming we are all at war with each other. […]

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Humor — People are so disconnected from one another today and we’ve gotten way too serious. I have a very dry childish sense of humor that comes out in what I write. I think the world needs to lighten up a little, laugh a lot more. And stop assuming we are all at war with each other. Laugh at what goes wrong, laugh at the things you can’t control, laugh at the ridiculous situations we often find ourselves in. Encourage others to laugh along with you.

How does a successful, strong, and powerful woman navigate work, employee relationships, love, and life in a world that still feels uncomfortable with strong women? In this interview series, called “Power Women” we are talking to accomplished women leaders who share their stories and experiences navigating work, love, and life as a powerful woman.

As a part of this series, I had the distinct pleasure of interviewing Nikki Webster.

Nikki Webster is a travel writer who owns a successful travel website. She covers how to travel while grinding a day job without breaking the bank. Provides detailed hotels reviews, cruising insight, and off-the-beaten-track experiences. She is particularly fond of Florida and writes extensively about the state. She flies around 60,000 miles per year and has visited 54 countries, 50 states, and six continents.

Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your childhood “backstory”?

I grew up in the inner city of Leeds, a large city in England. Despite being academically gifted and the recipient of a scholarship to an acclaimed private school — I dropped out of school at fifteen. Already wild at heart and ready to pursue life as an adult.

I was still a child, only I did not realize it at the time.

I was on a mission to defy the age old “your parents know best” and prove that I would be the exception. I knew what was best for me and could make it with no education or real work experience.

Couple this with my rebellious exploration of all things a fifteen-year-old should not be doing and I became lost for a while. I think most would say lost forever until I had the fortune to see the light.

The light for me was to remove myself from the situation I was in. I disassociated with all those I knew and ultimately moved to another country.

I applied to The University of Central Florida and moved to America. I am the first person on both sides of my family to go to university and the first to earn a degree. This was my turning point.

Can you tell us the story about what led you to this career path?

I’ve been working in Corporate America for over twenty years. I lead a team that manages Professional Development. I love my job and I am fortunate to have it. Yet, I’ve experienced the glass ceiling. Factors like the need to re-locate, conforming to clicks and the need to be a “yes” person or play Switzerland have driven me to reinvent myself.

A couple of years ago, I started what I thought would be a quasi-hobby documenting my travels. This started because I am known for scoring the best deals through a combination of travel hacks. I was constantly sending long emails outlining the process. Eventually, I decided to create a website and post the content.

Initially, I did not realize that this could become a business. Within a year I saw the opportunity and began aggressively learning everything about affiliate marketing, search engine optimization and how to technically run a website.

Can you share the most interesting story that happened to you since you began your career?

I think the most interesting thus far is that I was contacted by a local tourism bureau that had been following my journey. They liked my style and my philosophy which is: You only get one life and tomorrow is not guaranteed.

They reached out and asked me to visit several spots in Central Florida and then write about my experiences. It was the first time that I really knew I was on to something.

This experience took me to places in Florida that I’ve never been to before and I got to go on an actual safari in Florida!

You are a successful business leader. Which three-character traits do you think were most instrumental to your success? Can you please share a story or example for each?

  • Honesty

I vowed when I started my website that I would tell the good the bad and the ugly. Naturally, anything ugly comes with criticism and I’ve had plenty.

Regardless, I will always share what I think and articulate why I think what I think. I also support any data points with fact and try to avoid emotion.

It’s something that people either love about my site or hate. Either’s fine with me.

  • Integrity

I get contacted by numerous brands daily offering me all kinds of swag in return for an endorsement, backlink or shoutout. I turn most if not all down. If I would not use the product myself it’s not a fit.

Likewise, if I am already brand committed to a certain product, I will not flip just to gain another revenue stream. Some people will say that this is leaving money on the table — it may be but it’s deliberate.

If my name is attached to something, it must be something I can stand behind wholeheartedly and I will not bend on this.

  • Humor

People are so disconnected from one another today and we’ve gotten way too serious. I have a very dry childish sense of humor that comes out in what I write. I think the world needs to lighten up a little, laugh a lot more. And stop assuming we are all at war with each other.

Laugh at what goes wrong, laugh at the things you can’t control, laugh at the ridiculous situations we often find ourselves in. Encourage others to laugh along with you.

Be a human and display your human traits.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. The premise of this series assumes that our society still feels uncomfortable with strong women. Why do you think this is so?

I think there are several reasons:

  1. We’ve been conditioned to believe and accept this. From a young age our parents do this subconsciously. They may encourage us to go for it, but they also encourage to conform to norms in subtle ways like get married, buy a house, or have a child. It’s compounded when you enter the workforce. Many traditional biases still exist such as “will she cope” if she has a child. Or “Can she do this if she has child?”. Even conversations around schedules and ability to travel have a different context for women.
  2. Corporate America is still run by old white men. How many women are on the list of the top ten richest? None. How many women CEOs are there compared to men? Few. The lack of role models to follow reinforces these social norms.
  3. Women are expected to be maternal, softer in tone and feminine. And women are consistently judged on their appearance. Too pretty, not pretty enough. Too much make up, not enough. My experience is it’s too much or not enough of almost everything is the norm.
  4. We’ve never had a female president. Shocking for the country that is meant to set the stage for the world. This alone speaks volumes to where we are as a country relative to women.
  5. Women’s rights are consistently up for debate. Be it under the umbrella of science or religion. It’s always women’s rights regarding their bodies and never men’s. Both sexes seem to accept this travesty in mainstream America.
  6. Many women that rise to the top do so under a male like persona. Time and time again I see women emulate men because they assume it’s the path upward. It’s perfectly acceptable to be the woman that you are!
  7. Some women at the top of the want to be the only one at the top. It reminds me of high school where there is the dominant female, and the rest are followers of “her”. I firmly believe this is learned at an early age. Women compete with other women for men in their youth for love. They compete with them as adults for status, power, and money. It’s not needed. The only person you should compete with is yourself.

Without saying any names, can you share a story from your own experience that illustrates this idea?

Yes! Earlier in my career I was coached that it would be to my advantage to wear a suit. I’ve never liked suits and I don’t think they are flattering on women. I find pant suits particularly masculine. Sure, they command a certain perception, but they are anything but feminine. I took the feedback for what it was worth. Ultimately decided that’s just not who I am. This may have cost me an opportunity or two along the way — so be it.

I’ve also received coaching about being open to relocations for roles. I moved from England to live in Florida — a place that I love. I have zero interest or intention in uprooting to gain a leg up.

Another example is I have a very direct and sometimes abrupt manor. I tend to call things as I see them. I’ve had lots of feedback on this over the years. It’s warranted and I have modified my style to be much more diplomatic and collaborate. However, I have never wavered on calling a spade a spade. I just do it now in a way that’s not as gruff. Despite modifying my stance, I am still considered “gruff”, yet male counterparts are not.

What should a powerful woman do in a context where she feels that people are uneasy around her?

  • Be open and share her authentic self. Be real, be vulnerable. Far too often vulnerability is seen as a weakness. It’s not, it’s what opens the door for others to understand you.
  • Seek feedback from others and create an environment where people feel comfortable giving you honest candid feedback.
  • Create trust by demonstrating that you can be trusted. Show people that they can trust you through your actions.

What do we need to do as a society to change the unease around powerful women?

  1. Accept the reality that when it comes to competency and skill women and men are equal. This is an example that can’t be debated. There’s no science or study that states either of the sexes is more intelligent or competent than the other. The human brain plays a role in sexual desire, but it is sexless organ. The human brain has no gender, and everyone’s brain is unique.
  2. Demystify What Leadership Really Is. Along with cultural and organizational bias, there is still a strong hidden belief that men are somehow better at leading. There’s no viable or conclusive data that indicates one sex is better suited to lead than the other. It’s time to de-sex leadership!
  3. Educate women and men about second-generation gender bias. Most assume that gender bias is a thing of the past. It’s not, it’s just showing up differently in the second generation of leaders. These barriers are often invisible and come from cultural assumptions and organizational structures and practices. These inadvertently benefit men and create disadvantages for women.
  4. Celebrate them! We need to support and celebrate successful women. This includes women supporting women. Women are notorious for tearing apart other women. This needs to stop. Women of power or in a power role have a responsibility to raise other women with them — not stifle them. The same is true for males in the workforce. They need to support women and treat them as equals.

In my own experience, I have observed that often women must endure ridiculous or uncomfortable situations to achieve success that men don’t have to endure. Do you have a story like this from your own experience? Can you share it with us?

Absolutely! I live in Florida where it’s 80 degrees plus year-round. A prior CEO instituted a policy that mandated a policy of women wearing a dress or skirt to wear pantihose. Can you imagine? This was not that way many years ago. I was appalled, disgusted, and horrified. I also never complied.

In your opinion, what are the biggest challenges faced by women leaders that aren’t typically faced by their male counterparts?


Women must work harder, do more research, and provide more facts to be taken seriously or be considered credible.

Whereas with men, credibility seems to be assumed. And, when not assumed it’s anointed under a good faith umbrella by other men. Rarely will you see this be the case for women.

I’ll also add that its far more common to see a male rise and lead who has no experience or qualifications. Whereas the female counter parts are told they “Need more experience” or “They are not ready yet”.

Society is still more apt to taking a risk with a lesser qualified male than the female counterpart.

Let’s now shift our discussion to a slightly different direction. This is a question that nearly everyone with a job must contend with. Was it difficult to fit your personal and family life into your business and career? For the benefit of our readers, can you articulate precisely what the struggle was?

I think the need to “out work” males for leadership roles creates the biggest hurdle. I’ve come to accept this — right wrong or indifferent. Sometimes, you must do what you need to.

I’ve led large teams deploying new technology to the enterprise and had to work on vacation. For example, physically testing system functionality while on vacation in Mexico. I could look at this as an infringement. I don’t, it comes with the territory — and it’s not something that happens very often.

When my family gets upset that I have to work, I remind them where the money comes from for the vacations we all enjoy. I also remind them that it’s not all the time that these situations happen.

Now that I am running a company, my family deals with my time constraints even more. I’ve found that scheduling time for work and play makes a difference. However, I still run into scenarios where the work needs to come first. Again, I remind everyone of the long-term goals and how we all benefit.

Lastly, in my house everyone has come to terms with the reality that I am the bread winner. I’m a firm believer that whoever has the most earning power should go for it. This is not always the male and there’s no shame in that at all. Society needs to start embracing this idea.

What was a tipping point that helped you achieve a greater balance or greater equilibrium between your work life and personal life? What did you do to reach this equilibrium?

I set boundaries and schedule all my time — personal and work. I then rank what’s on the list for the week ahead. What is absolute and what’s a nice to — or what can wait?

For example, when I have deadlines, they must be met they are at the top of the list. If we have a trip planned, I look further out than a week and see, what can I do to eliminate some of the workload before the trip.

The tipping point for me to balance my time was when I experienced chronic burn out. I took a solo week of vacation to re-asset my goals and to plan how I would balance my time.

I work in the beauty tech industry, so I am very interested to hear your philosophy or perspective about beauty. In your role as a powerful woman and leader, how much of an emphasis do you place on your appearance? Do you see beauty as something that is superficial, or is it something that has inherent value for a leader in a public context? Can you explain what you mean?

I place this much on it — I need to look professional, clean and put together. This means different things for different people.

I think beauty is superficial. I also think that in the context of ability to lead it’s irrelevant and stereotypical.

This said, enter a traditional corporation that’s been running for fifty plus years and study the women executives. They all look alike, even down to the same muted nail polish.

How is this similar or different for men?

I think men have this challenge as well. There are expectations that men dress a certain way. The boring atypical monotone suit with the starched shirt. The cuff links, the monograms, and the leather shoes. They all dress the same as the follow the examples set by those at the top.

I think dress code expectations are more stringent for men. There’s little room for expression for men in corporate America.

Ok super. Here is the main question of our interview. Based on your opinion and experience, what are the “Five Things You Need to Thrive and Succeed as a Powerful Woman?” (Please share a story or example for each.)

  1. Determination

You must be fiercely determined if you are going to make it. No exceptions. Failure will happen, it should be expected. Pick yourself up off the floor, assess the situation and go back at it.

2. Self-Assurance

No one other than you can determine your worth. You determine it, you control it — own it.

3. Never Play the Girl Card

Believe or not, some women still play this hand when they think it will benefit them. We’ve all seen it. The subtle flirting, the hair flip, the eye fluttering. In extreme cases, the high-pitched voice. There is no place for this at work. Any time a woman resorts to this they take us all back ten years. And this is a sure path to being public enemy number one with other women.

4. Align with the RIGHT People

Think about your values here. Who are you, what do you stand for and who do you admire and why?

Too often people align with people in a power role simply because they are in the role. It may help you climb but you may also climb in a way that’s not authentic or even comfortable.

You may find yourself rising but to a place you never intended to be. Or worse, a place where you need to sell your soul.

5. Treat Others as You Want to Be Treated

A wise mentor once gave me two pieces of advice:

  1. Treat everyone as equal
  2. Watch how others treat others.

We all know we are to treat others as we want to be treated but let’s go deeper:

  1. Say hello to everyone including the cleaning crew. I make a point to say hello and ask them how their day went. I also say good morning to all the security staff, the meeting center people and so on. You’d be surprised how much being nice and interested in people does for you. I’ve been in many a jam where these people that a leadership role may not have will go out of their way to help me.
  2. Observe how others treat people. Watch for those who dismiss the cleaning crew or others that they deem lesser. Learn from this, don’t be this person.

We are very blessed that some very prominent 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 with, and why? He or she might just see this if we tag them.

Well, there are few:

  1. Richard Branson — Richard Branson overcame dyslexia and is now one of the most successful businessmen of all time. Not as famous in America as throughout the rest of the world but he is one of a kind. If you have never experienced a product from Richard Branson, you have not lived. I have been a long-time fan back to the days of the brick-and-mortar Virgin stores. Now, I fly Virgin whenever I travel to England. Let me tell you — everything Sir Branson does it 1st class. Even in Economy on Virgin Atlantic is like flying business class. I have also flown Virgin Australia — flawless. And I have stayed at the Virgin hotel in Chicago. Sir Branson has the Midas touch, everything he does is on point. Lastly, he is known for putting his employees first.
  2. Anderson Cooper — I consider Anderson to be the voice of reason in a world full of lies! Some will disagree but I have followed him for years and he is factual. For me, this is integrity. He is also a humanitarian; he uses his voice to promote change and I really admire this. Lastly, despite being born into a Vanderbilt life he is self-made!
  3. Cutis Jackson — 50 Cent. I think he said it best. “He did not go to Harvard but the people who work for him did”. Successful people surround themselves with successful people. They also hire the people that can do the things they cannot. This is a man who came from nothing to a rapper, businessman and of course now he is the “King of Instagram.”
  4. Nicky Jam — He moved to Colombia because he needed a new environment to overcome challenges and to pursue his career. We have different stories but share the same motivation to move. I have experienced many of the challenges he had growing up. I am inspired by how he reunited with his mother after 20 years and was able to forgive.
  5. Oprah Winfrey — I am sure that everyone has Oprah on their list. Perhaps the most inspiring woman of all time. The obstacles that she has overcome and prolific, the odds were against her from birth and yet here she is — a modern day Mother Teresa. Outside of her business success, I am always inspired by how much she gives back and the charities she chooses. I also think she is brutally honest a trait I think is critical.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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