Heather Monahan, 43
Founder of Boss In Heels (and in recovery from corporate America)
Heather Monahan is a boss in every sense of the word. After spending the bulk of her career climbing the corporate ladder, the rockstar executive and single mother decided to abandon the proverbial hamster wheel and instead dedicate her life to helping women squash self doubt. Her initiative, rightfully dubbed #bossinheels, aims to destroy the male-oriented vision of what being a “boss” means. “Become your number one cheerleader instead of your biggest saboteur,” advises the blonde beauty. “It will change your life.”
1. What made you choose this career path? What has been your greatest achievement?
My entire life has led me to where I am today. Having struggled with my own insecurities early on and not having a strong female mentor led me to the decision to empower others and give them the insight I was always searching for. While working in corporate America and doing what I thought I was supposed to do, I stumbled upon what I was meant to do. It didn’t happen overnight it was more of an evolution over time. As I grew more confident in myself it became overwhelmingly clear what I needed to do; I needed to be the person that I needed when I was younger, I needed to shine my light so others could see. My greatest achievement is risking my comfort zone to be the person I am becoming and showing my son through my actions not just my words that everyone should live up to their potential and chase their dreams.
2. What’s the biggest criticism/stereotype/judgement you’ve faced in your career?
You can't dress feminine and be taken seriously.
3. How did you #SWAAYthenarrative? What was the reaction by those who told you you “couldn’t” do it?
My own self-doubt. To overcome self-doubt you must take action and develop your confidence muscle. Who you surround yourself with is everything – fire negative people in your life and watch you take off. How you see yourself is how others will see you – speak kindly to yourself, make yourself a priority, love yourself the same way you would a baby – this takes practice but it can become a habit.
Journal to see how far you have come and keep track of all of your small wins. Turn scarcity into abundance by writing down three things a day that you can be grateful for. Moving into your fear and realizing that you are okay will give you strength for your next challenge while backing away does the opposite. Speak up in meetings, speak up for yourself and speak your truth. Becoming your number one cheerleader instead of your biggest saboteur will change your life. Go for it!
4. What did you learn through your personal journey?
Early in my career I was taken aside by a very stoic and cold woman who told me that I dressed inappropriately for work and needed to wear pantsuits and more formal conservative attire. I have never been a very conservative pantsuit type of girl so this conversation didn’t go well.
Time and time again in my career I have been told to look a certain way or dress a certain way and with much difficulty, I did not listen. I was sexually harassed at my first job and was told that the way that I dressed invited these types of challenges.
Years later I remember being at a company meeting and sitting in on a roast where I was tagged the “VP of Cleavage” apparently this was a knock at the strapless dress I was wearing. I excused myself and cried in the bathroom for a few minutes before composing myself and returning to the meeting. The ironic thing is in the past year as I have launched my personal brand to empower others, I have heard so much positive feedback and appreciation for my sense of style. Believing in yourself and being yourself will always pay dividends in the end but isn’t always easy along the way. Be true to you.
5. What’s your number one piece of advice to women discouraged by preconceived notions and society’s limitations?
The only limitations that can be put on you are the ones that you put on yourself. Make a conscious choice to challenge the status quo. I learned that Oprah was fired from TV many years ago, only to become the media maven that she is today. Everyone will be told ‘no’ and why they are wrong or not good enough, and those are the moments you pivot and find a way to make it work in spite of the negativity. If success was easy everyone would have it. Let nothing stop you in chasing your dreams and nothing will.
3 min read
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Help! My Friend Is a No Show
Dear Armchair Psychologist,
I have a friend who doesn't reply to my messages about meeting for dinner, etc. Although, last week I ran into her at a local restaurant of mine, it has always been awkward to be friends with her. Should I continue our friendship or discontinue it? We've been friends for a total four years and nothing has changed. I don't feel as comfortable with her as my other close friends, and I don't think I'll ever be able to reach that comfort zone in pure friendship.
Dear Sadsies,I am sorry to hear you've been neglected by your friend. You may already have the answer to your question, since you're evaluating the non-existing bond between yourself and your friend. However, I'll gladly affirm to you that a friendship that isn't reciprocated is not a good friendship.
I have had a similar situation with a friend whom I'd grown up with but who was also consistently a very negative person, a true Debby Downer. One day, I just had enough of her criticism and vitriol. I stopped making excuses for her and dumped her. It was a great decision and I haven't looked back. With that in mind, it could be possible that something has changed in your friend's life, but it's insignificant if she isn't responding to you. It's time to dump her and spend your energy where it's appreciated. Don't dwell on this friend. History is not enough to create a lasting bond, it only means just that—you and your friend have history—so let her be history!
- The Armchair Psychologist