Four Female Chicago Leaders Give ‘Advice to My 20-Year-Old Self’

March is National Women’s History Month, so we reached out to some notable Chicago women and asked them: “What advice would you give to your 20-year-old self?”

The answers didn’t disappoint, and they included thoughtful reflections on life experiences, the importance of perpetual curiosity, and a painful memory about a missed opportunity with Barack Obama.

What advice would you give to your 20-year-old self?

• Hard work pays off.  You should focus on your career, but know that the opportunities will be there if you work hard and people believe that they can count on you.

• Don’t worry so much. I know you won’t be able to hear this, but just don’t worry so much. It will be fine.

• Learn to say no. It is better to just say “No, I don’t have time for something” than to say yes but be so pressed for time that you don’t perform or live up to commitments.

• Talk to everyone — build a wide network of friends and colleagues. 

• Continuous learning is critical. Get that advanced degree, take that certification course. Do it now, because life, relationships, and family gets more demanding and the time does not get easier to find. 

• People first. Pick jobs and opportunities based on the people you will be interacting and working with… not just what you will be doing.

• Wear sunscreen!

Be Comfortable with Being Uncomfortable
Hit the pause button to reflect on lessons learned, but don’t get caught up in the past. Focus on the future and allow yourself to take risks. Step out of your comfort zone and challenge yourself to accomplish what you might not even know is possible. If you try to choreograph your every move, you will miss opportunities that can be game-changers.

Be Intentional
Be intentional with how you spend your time. You won’t necessarily love every minute of every task, but overall, your time (personally and professionally) should drive up to a larger goal. Earlier in my career, I worked around the clock and never once thought about what was next. As a result, I missed opportunities to expand my network and make meaningful connections. Best example: I was in the elevator when then-U.S. Senate candidate Barack Obama walked in with a mutual friend. My friend introduced me as a “PR pro.” I was invited to meet with him, but I was so busy managing the chaos of my current job that I never followed up. Oops!

Know Your Brand
Picture yourself walking into a board meeting. Before you even say a word, what will that first impression be? How will people remember you? Or, maybe here’s a better question: Will they remember you? I never really thought about this until later in my career, but every interaction, no matter how big or small, is a chance to leave your mark. Lean into your power to maximize every opportunity, because you never know where your career journey will take you.

• Trust your gut and be fearless. You’ll soon realize that you’re a dreamer and a natural optimist. With that, you’ll be told that you’re too much, your dreams are too big, too ambitious, and unrealistic — but don’t let others dim your light. Instead, listen carefully to your fire and intuition. You’ll be the first, or the only, in many of the spaces you’re in, but take up space.

• There will be so many opportunities to re-invent yourself, so don’t worry about making the wrong decision. Very few decisions in life are actually irreversible.

• Life will be far more beautiful than you could have imagined. You’ll find love sooner than you anticipated, but you’ll know it. He will be a wonderful partner who loves you for your big dreams and optimism. Your kids will be the most incredible humans you meet, and they will bring you so much joy.

• Going to the University of Michigan, even though it’s miles from home and you don’t know anyone there, will be one of the best decisions of your life. Go Blue!

• Wear those colorful outfits. You’ll stand out in the best way possible.

Dear Younger Self –

• Trust the process. You are on the right path. Your interests are not accidental, they’re hints of your purpose.

• Know your worth. You must find the courage to leave the table if respect is no longer being served.

• Whatever you’re thinking, think bigger. The size of your dreams must always exceed your current capacity to achieve them. You are a product of your decisions, not your circumstances.

• Motherhood goes by fast. Cherish every musical theater show and movie night. You’re doing an incredible job as a mother. Trust yourself, embrace the journey, and know that you’re making a difference in your child’s life every day. She is courageous, brilliant, and a superstar.

• Trust in the timing of love. Finding the deepest lifetime love is a journey that requires patience, self-awareness, and an open heart. Remember, true love starts from within. Fall deeply in love with yourself each and every day. Read that last sentence again. Embrace your own flaws and strengths and learn to love yourself fully before seeking it in another. You will find him and fall deeply in love with him every.single.day.

With love and encouragement,

Your Hopeful Self