Full name?: Jessica Ekstrom
Position / Job title?: Founder and CEO of Headbands of Hope
When you were a kid, what did you want to be when you grew up?
I always wanted to be a journalist. I loved writing and telling stories, so I thought journalism was perfect for me. I got really caught up in the idea of writing for a shiny NYC magazine. I was definitely more focused on the “looks” of the job and not as much the purpose.
Fast-forward several years/decades. How did you land (or create) your current position?
When I was in college, right before my 20th birthday in the summer of 2011, I did an internship at a wish-granting organization.
Everyday, I got to wake up and grant the wishes of children with life-threatening illnesses. I took day trips to visit the wish kids at their houses and bring them their favorite toys. We received hundreds of letters from wish children that said we changed their lives; little did they know, they were changing mine.
One day, I was pulling my hair back in a ponytail and thought about the hundreds of girls I encountered that lose their hair to cancer. I saw how much losing their hair had an impact on their self-esteem and confidence level.
I thought about the thousands of girls around the world losing their hair to chemotherapy. Being a young girl presents many struggles with self-esteem already and losing their hair as a result of a life-threatening illness is traumatic. Not only do they have to face the risk of losing their lives, they feel that they lose a part of their feminine identity. Therefore I started Headbands of Hope. For every headband purchased, one is given to a girl with cancer and $1 is donated to fund childhood cancer research.
Did you have to take on internships to get there? How important in general, do you think, are internships?
Even before my Make-A-Wish internship, I interned my freshman year in Disney World. When I worked there, I discovered the Make-A-Wish Foundation. From that internship, I became inspired to start Headbands of Hope, and then my life changed.
If it wasn’t for starting internships early in my college career, I may have never discovered I didn’t want to be a journalist. Internships aren’t just resume builders. They help you discover what you like and what you don’t like, what you’re good at and what you need to work on, what you believe in and what you don’t.
What you learn at internships can be really hard to learn in the classroom. They’re such a growing opportunity for you professionally and mentally.
Tell us what a typical work day looks like for you. What is your job REALLY like, both the glamorous and not-so-glamorous parts?
I never feel like I’m not working. There’s no clock-in and clock-out, on the clock or off the clock.
Headbands of Hope isn’t just my job. It’s who I am and it’s infused in all areas of my life. I hope when people meet me they associate me with my company. I’ve built an empire that I’m proud of and that I believe in. I get to wake up every day and change lives. I don’t need that to be separate from who I am “off the clock.”
As an entrepreneur or even if you work a 9-5 job, love what you do so much that you don’t have to separate work to one side of your brain and life luxuries to another. Find what’s important to you, and then have the courage to cater your career around that answer.
One day I might be visiting a children’s hospital and spending time with the kids. Another day I might be catching up on emails and creating new line sheets for our stores.
Every day is different. You could categorize some days as more “fun” than others. But you could never categorize some days being better than others. No matter what I do, boring or exciting, it’s helping a girl get a headband.
What is the biggest career mistake you’ve ever made?
When I first was starting my company when I was 19, I lied about my age. I thought the fact I was so young, people wouldn’t take me seriously and they’d just stamp “millennial” on my forehead. I quickly learned that being young was one of my biggest strengths and something I should be proud of.
I’m now a public speaker at colleges across the country to show them that you’re never too young to start something you believe in. I also show them how college is actually a great time to go for it.
If I didn’t embrace my age, I would never be put in a position to serve as a role model for my generation.
What is the single most important piece of advice you would give to other career-minded women?
Before you take another step, sit down and figure out your definition of success. What does success look like to you? I’ll tell you right now, it’s not going to come from a paycheck, a position title, beating a competitor or any kind of tangible achievement. You can appreciate those as milestones that you’re on the right path, but don’t confuse them for success.
Think about waking up every day. What will make you excited to get out of bed? Discover a clear connection between what you’re doing and why you’re doing it. Once you have that, work won’t feel like work.
Let’s talk about work/life balance. What does that mean to you? Is it important?
Some people could categorize me as a “workaholic” because I’ll do emails on weekends or skip a football game for something Headbands of Hope related.
As CEO of my own company, it’s always my responsibility 24/7. Therefore, I feel inclined to always be “on the clock.”
But lying in bed at 11:00 pm with the lights out and answering emails isn’t exactly the best habit in the world.
I learned that I need to pick and choose my battles with being “off the clock.” If someone emails me when I’m at dinner about planning a fundraiser that can wait until tomorrow. If I get an email that our website has crashed or has a glitch, that’s a good enough reason for me to power up my computer before I call it a night.
This “unplugging” thing is still an issue I struggle with. I don’t think I’ll ever be perfect at it, but I can always try to be better.
On that note, do you think women can have it all? Both the baller career, and the happy family?
Just like my definition of success, I think a woman (or a man) has to decide what “all” means to them. Maybe they don’t want to have the baller career while having a family or visa versa, which is totally fine.
But if you want both, it can be done. Right now, I’m 23 and don’t have the responsibility of raising a family yet. However, when that does happen, you can find ways to make it work. Having a supportive spouse and co-workers is crucial. Both sides need to understand that the other side is important to you.
If you could look into a crystal ball and see 20 years into your future, what would you want to see?
20 years from now I’ll be 43. I’d love for Headbands of Hope to not be around because there’s a cure for cancer. I hope that happens by the time I’m 30 actually!
When that’s the case, I’d love to take my experiences and help others with socially-conscious startups.
Do you have any career role models? Who are they?
My dad. When I was in middle school, I remember my dad sitting us down as a family and tell us he had a business idea. He asked if we’d support him in quitting his day job to pursue his idea. Being only 13, I was like, “sure, what’s for dinner?”
I didn’t realize the magnitude of what he was doing. I saw first-hand what it was like to have an idea and take that leap. He poured everything he had into starting his business. His business was a hit and he just recently sold it and retired at 55. But it really wasn’t the money that inspired me, it was the freedom to create your own destiny that he showed me.
He had a secure job, but he didn’t believe in it. So he created something he believed in.
I remember one time we were camping when I was 15 and I said, “Dad, wouldn’t it be cool if my headphones just rolled up instead of getting tangled? Can I invent that?”
He sat down beside me, took my hand, and said, “That’s already been invented, but keep thinking like that.”
From then on, I did. Then one idea finally became a reality!
What is the best piece of advice that you have ever received – career-related or otherwise?
The best advice I’ve ever received is about failure. There will always be people that say “no” to you. There will always be people that shut doors in your face. But it’s what you do after that really counts. I choose to view failure as I’m on the right path. If I’m not failing at anything, I’m not trying hard enough. Therefore, when a door shuts in my face, I’m not upset because it shows I’m pushing myself. And if it’s a door I really wanted, then I’ll keep knocking…and knocking…and knocking.
Parents love to say, “just wait ’til you have to face the real world…” When you were in college or high school, what did you think the “real world” looked like? What is the difference between what you thought and reality?
Luckily, my parents never really raised me in a bubble or sheltered me from realities. They were very healthy at raising me to always help others and to always gain experiences (good and the bad).
However, in school my “real world” was instilled in me as high school, college, and then you had two choices between grad school and getting a job. Entrepreneurship was rarely listed as a third option.
I’m not big into regrets or time machines, but if I were to go back in time, I’d take a gap year between high school and college to travel and do volunteer work.
We’re always in a rush for the next thing. You go straight from high school to college. Then from college, if you don’t have anything lined up the day after graduation, you feel discouraged.
For me, I had Headbands of Hope during college and then it grew into my fulltime job, so I didn’t have the opportunity to take a gap year post-college.
So for me, the real world wasn’t a rude awakening, but rather an eye-opener to all that it has to offer.
Should you work for the money, or do what you love?
I’m not naïve to think that money isn’t a factor. It is. But I don’t think you should have to choose between making a living and making a difference. You should be able to do both at once.
This is easier said than done (but not impossible): find what gives you purpose, then find a way to make a living off of that.
How important is money to you when considering a job?
I wanted to be able to put 100% of my time and energy into Headbands of Hope. If I had to hold down 3 other jobs and get loans and a ton of investments to keep the business going, it wouldn’t be what it is today.
To me, money doesn’t mean a new car and brand name clothing. But it does give you an element of freedom to explore and help others. The importance of money isn’t what’s on your paycheck, but rather how you’re going to use it.
What is the single most important factor of a job?
Remember why you started. If I’m ever having an off day or I’m frustrated or there’s a glitch on the website, it’s easy to let your frustrations get to you and you want to give up. But giving up isn’t an option, because I could never give up on those girls in the hospital. I just have to remember why I decided to put everything I had into this, and then I feel inspired to work even harder.
If you married a millionaire husband and didn’t have to work, would you? (Be honest.)
Some days you can fantasize about having a bulk of money just appear in your bank account whether that’s from a spouse’s job or winning the lottery.
Sure, that would be nice…but then what? I’ve never been the kind of person who feels fulfilled after a long day at the salon then have my personal chef cook me dinner (okay maybe that would be fun for like a day). But it’s not realistic that it would make me happy long-term. I need something to feel like I have purpose in the morning. Maybe that comes from being a mom and a wife, or maybe that comes from my job. But whatever that purpose is, money can’t buy it.
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