A Love Letter, 5 Wishes for Female Leaders Who Feel Like They Have to Prove Themselves



Today I'm writing you a very personal and vulnerable letter. There are parts of me that are saying no don't do this, but I know I have to. So here goes.

For as long as I can remember, I've always been passionate, creative and driven. I’m the person who gets shit done! I’m a classic overachiever. I’m the one who loves getting up at 5am making the 5:30am Crossfit class and being at my desk early to take on the day. I loved the adrenaline of working hard and feeling like I was kicking ass. In my last review at eBay, my peer feedback was I worked too much.

I was a step ahead. Always on my toes. Ready with an answer. Well, that’s the picture the world got to see. Here's the truth.

I’ve always felt behind. That I wasn’t good enough and that I had something to prove.

Growing up my father was in the Air Force. We moved often and starting my education in Europe, when I got to the US I was constantly behind with gaps in my education. I’ve needed tutors over the years and had the knack of joining a new class right before a big test. Nothing like starting school on Monday with a test on all the capitals of The United States on Tuesday. It was a lot of pressure to keep up and constantly make new friends.

It wasn’t until Junior High and being at the same school 3 years in a row that I started to show aptitude. I still remember today, the one year I was at the top of my class receiving student of the year ribbons in several classes. It’s the moment in my life where I felt the most accomplished and proud. It didn’t last long. The next year I was placed in advanced classes. Once again I was behind, very behind.  Once again I had something else to prove. That feeling never went away.

By college this was just how life was. I lived off of scholarships and worked 2-3 part-time jobs, along with taking a full schedule at school so I could double major. Do you see the theme? By Christmas of my senior year in college, I had two job offers. When my first offer arrived in the mail, I ripped the envelope open. The salary jumped off the page. I did it! Now what? I had just turned 21 and felt like my life was over.  It turns out I was living my father's dream--be a good girl, go to college and get a good job. The dream was over. Now what?

For the longest time, I didn’t know who I was and what I wanted. I did what I thought I was supposed to do--work hard and create a life for myself. After several years of working 50-60 hours a week and commuting 2-3 hours a day, I was burnt out and had severe back pain. Advil, wine, chiropractic visits... nothing helped. This was my first wake up call. Something had to change. It did for a time but then I slipped back into old habits.

After graduating with my Masters of Science in Organization Development (OD), I was attempting to do something I hadn’t seen anyone else do, move from Technology into Human Resources. I took a risk and took an interim job to demonstrate that I could make it in OD. At the end of the time, I was told that I wasn’t a fit for the role, yet asked to stay and backfill the position until someone was hired. Instead of giving up, I decided to prove them wrong. I eventually did but the stigma stayed with me.

I loved OD and supporting leaders in creating strategies for their talent, designing programs, and developing talent. However, my ego was getting in the way. I worked a lot and fell into the I don't sleep enough adrenaline trap of living and working in the California Bay Area. Life went on and I thought I had it all. I got married, owned my first condo in San Jose, and had said yes to my dream job. Even with all of that, something wasn't right and the life I built fell apart. There was a period of 6 weeks that I could only sleep 2-3 hours a night, slowly losing my mental acuity and all of my energy. When I started to sleep again it was clear something was wrong. I began to see what a lifetime of physical stress, work pressure, and self-doubt could do. With the help of an amazing functional medicine doctor, I started to recover from Stage 2 Adrenal Dysfunction and a myriad of digestive issues. The process had me re-evaluate my life, quitting a job that didn’t nourish me and leaving my marriage. Over a period of two years, I wandered through a dark night of the soul. Mary Oliver's quote "Tell me, what it is you plan to do with your one wild and precious life?" haunted me. It's the foundation of this love letter to you.

Friend, I know that we all have to go through our challenges and have our lessons to learn. I’m hoping my story and these 5 wishes will give you pause. Pause to listen to your heart and make changes now before it's to late.

#1- Define who you want to be.

Decide now who you want to be. What are three attributes you want to live towards? When you are with others how do you want to treat them? Let this be how you live your life and your proof. My words are beauty, grace, and truth; with a bit of magic mixed in.

#2- Let go of beliefs that don't let you live a life fulfilled and seen.

We grow up with cultural beliefs dictating who we are who we should be. If you are at all like me some of these beliefs may be familiar. “Be a good girl.” “Don’t do that it’s not ladylike.” “Good girls are seen but not heard.” “Be quiet!” The list goes on.

It's time, time to let these stories go. I know it's a risk to our very belonging to stand up and speak up. It's worth the risk. It's the only way to say yes to yourself, even if the world isn't. When you are tempted to be quiet to stay small, I wish that you'd be curious. Is there a story running in the back of your mind, a lingering cultural belief. If so, take a moment to choose if this is something you want to continue to believe. Ask yourself, is this something I'd wish for a friend? Is this something I'd teach to my daughter?

#3 - Define success for yourself.

Maybe you grew up like me and success was defined as graduating from college and getting a good job. Maybe you are like my friend Susie that her dream was to be married and have 2 children by the time she was 30. Perhaps your measurement of success is grander. Or maybe you’ve never stopped and defined what success is for you. This is your opportunity. Take a moment and close your eyes. Imagine that you are on your deathbed looking back at your life. Who do you want to be? What did you want to accomplish? Who do you want in your life? What is your legacy?

However you define success consider this, does it take in the whole of your life. Don’t just look at your title at work, how big your team is or what your paycheck is. There are so many other colors and textures in life than our status at work, how busy we are, how much we work out, how much we weight, or what’s in our closet.

#4- Be selfish and put your wellness first.

Be selfish! If you want to give more, you have to fill your cup.
Nothing should be more sacred than the time you need to care for yourself. Even if it’s a half hour a day, identify what you need and do it. Do your best to protect your sleep, to get up and stretch after being stuck in a chair all day, drink more water, less caffeine and alcohol, eat food that nourishes you, and say things to yourself that are encouraging. As I write this I write it to myself. We women give so much to others, yet always leave ourselves in the last place. The result is overwhelming burnout and health problems. Please learn from me.

#5- Know you are enough.

You are enough. We are enough.

We grow up in a world where our worth is compared to that of a man. Fortunately, you are in a place and time where we have it better than any generation that has come. Yet, there is so much more progress to be made. At work and in the world, we will often feel the stress and pressure to prove ourselves. While men are given opportunities based on their potential, we are looked at differently. Those times when you feel that pressure to prove yourself yet again, to be perfect and to not mess up please remember you are enough.

Choose to make your own standards and to show how beautiful imperfection is.

My final thoughts...

Living and leading, it's challenging. It calls us forth. To face our worst fears and doubts to find the best in us. One saving grace is that these challenges, these stumbling blocks, when faced become our stepping stones. Each a stone that paves our paths with courage and confidence. Stepping stones for every woman after us.

At the end of my life, I want to ask myself these questions...
  • Did I dare & rise?
  • Was I nourished and at ease?
  • Did I surround myself with beauty- in thoughts, in moments, in people and surroundings?
  • Did I live my truth?
  • Did I get into trouble?
  • Did I love?

Dearest, what is your list of questions that you would measure a great life by?

In closing, I wrap up this letter with gratitude. Thank you for being on the front lines of your life every day, trying to lead and make a better world for me, our daughters, and all the women to come. You are beautiful inside and out.

Remember, you’ve got this!

Much love,


    About the Author

    Kim-Elisha Proctor is an Executive Coach, teacher, and writer. For over 15 years, she has worked with companies at all stages of growth and understands the complexity of organizations and leadership that is needed for success. Whether one-on-one coaching, with groups or delivering leadership development programs, her passion is the same: to support leaders to enhance their performance, impact, purpose & well-being to create communities they long to belong to.

    Kim-ElishaAgency, Emotional Health, Lead Smarter, Personal Musings, Well-being