MintStyle with Rachel Weingarten: How to Have Confident Style


Quick: what’s the first thing you notice when meeting someone new?

Is it color of their eyes or hair? What about their shoes or car? While most people tend to focus on obvious details, the thing that usually stands out more than someone’s signature scent, socks or suit, is their attitude and sense of confidence- or lack thereof.

Think back to the last party or networking event you attended. Who did you find more appealing- the guy slumped in the corner avoiding eye contact, or the person smiling confidently and engaged in an animated conversation? I thought so.

Who do you think you are?

In the classic business motivational book Think and Grow Rich, Napoleon Hill reveals his “Self-Confidence Formula,” part of which advises the reader to begin “thinking of the person I intend to become.”

Hill was a firm believer in changing your attitude to change not only your circumstances, but the way that others perceive you. It’s almost a self-fulfilling prophecy: acting successful makes others believe you to be so, which in turn, leads you to act more confidently and so it goes. But the subtleties defining both confidence and success have changed in the decades since his book was published.

Evolving Confidence

In the ‘80s and ‘90s the kind of confidence personified by larger than life characters like Gordon Gekko and Donald Trump came with a swagger and personal style usually punctuated by flashy watches and foreign cars. In our own times, exuding confidence has taken on a different dynamic.

“I think the number one thing that a person who is confident is relaxed- they help other people to feel confident and good about what they’re doing,” says Michael Main, a senior partner at global consulting firm Oliver Wyman. He continues, “We all have tensions and doubts and some degree of nervousness and anxiety or ambiguity involved with the high pressure of doing business.”

Main believes that the modern business ethos includes thinking less about ourselves and more about the human connection, the greater good, and the benefit to the rest of the room. “People who do that naturally gain the trust of their peers and naturally find themselves in leadership positions.”

The Confidence Slump

But what happens if waiting to get to that that leadership position takes a toll on your confidence?

Michael Leibowitz, a recently minted MBA, remembers his time in business school fondly as almost a confidence building experience. Leibowitz enjoyed challenging himself and evaluating his skills as compared to those of his peers. He says, “Going through the program, measuring myself against people in my field, competing, feeling that I can do this – and do it well. It was a great confidence booster.”

It was the post-graduation job hunt though, that sapped his confidence. Surprisingly enough, it wasn’t rejection that got to Leibowitz; he welcomed helpful feedback from recruiters or interviewers. It was the self-described “black hole” of online job applications followed by silence or automated feedback that he found most draining.

Whenever I get into a confidence slump, I ask my big sister for advice. In this instance, my sister Rebecca Kiki Weingarten also happens to be an executive coach who works with those on the ‘C’ level, some facing this issue on a regular basis.

Kiki advises clients experiencing confidence sapping frustrations which occur on every level of the professional spectrum, to first and foremost create as bullet-proof a job application, letter of introduction or marketing materials as possible. “Use all tools available, from keyword optimization to spellcheck, to ensure that every element of your communications and applications stand up to initial computer analyzation,” she recommends.

Along those lines, Main researches all potential business partners before any meetings. Since sometimes LinkedIn profiles can be intimidating, Main might include a quick Facebook search. In that way, he learns not only about their professional achievements, but also puts a more personal and accessible face to potential clients and colleagues.

Kiki also advised making yourself as feedback friendly as possible by encouraging follow up – even when negative. And finally, keep sending out those applications and letters of introduction. “You’re not going to get a response from every single one, but you still have to send out every single one. It doesn’t measure your worth. It just means that you sent it out as a possibility. So don’t spend time focusing on what you didn’t get- focus on what comes back.”

Support Yourself

And if all that fails? Create your own personal support group- online or in person, get the people who give you the energy to say keep going! it’s not you.

For Leibowitz, this means his wife who cheers him on and reminds him that he can do as well or better in any job. He says, “People who know you best can remind you of your skills and not your failures.”

Jennie Phipps is a writer and editor who runs an online group and message board called Freelance Success. The group includes several hundred writers who act as both a professional sounding board and virtual support network for each other.

Over the years, Phipps has developed a thick skin and seeming imperviousness to outside criticism or rejection. When asked for advice on overcoming confidence crushing obstacles, Phipps advises remembering that while it might feel like a personal rejection to you, it’s not who you are personally – it’s what you’re doing.

She also advises persistence in pursuing your goals. She says, “It all goes back to the fact that it’s not you personally – it’s what you represent. People are wrapped up in themselves. If they don’t respond the first, second, third times- ask one more time.” Phipps says to take into account their busy schedule and remember that “asking them one more time gives them one more time to do the right thing and respond.”

Keep it (your confidence) up!

It isn’t always easy to look great, much less to feel great, much less to keep your confidence going when things are tough. But by knowing your own strengths, communication and interacting style, researching the competition, and being persistent you’ll have a better chance of succeeding.

Rachel Weingarten is a style expert, marketing strategist & personal branding consultant for CEOs, politicians and celebrities and the creator of MintStyle. She is the award-winning author of Career and Corporate Cool and Hello Gorgeous! Beauty Products in America ‘40s-‘60s. Rachel writes for top media outlets including CNN, Fortune, Forbes Life, MSN, USA Today, Yahoo Finance and many others. She is a regularly featured expert on TV shows including Good Morning America and The Today Show. Visit her online at or on Twitter @rachelcw