#23 | Telling Your Story With Jess Ekstrom

This week we got to sit down with author, speaker, founder, and all-around amazing human, Jess Ekstrom. This convo perfectly follows last week’s chat on resilience with Gemma Roberts, because all that Jess does is anchored in resilience’s best ally – optimism. I appreciated how she dove into teaching us how we can partner these two things together – a lesson we could all use as we continue to weather the storm that is 2020.

Jess is best known for Headbands of Hope, the company she founded at 19 years old (yes you read that correctly 19. As in when you and I were still figuring out how to navigate not living with our parents!) Jess is a beacon of light when it comes to purpose-driven work. Soaking in her innovative problem solving, tips for overcoming imposter syndrome, and how to jump headfirst into new experiences was just what I needed.

Starting A Second Business: What’s The Same Vs What’s Different (5:23)

As with most life experiences the first business venture is usually scary, but what happens when you go for it a second time? Fear shouldn’t be a factor, right? Ha! No even close!

When starting her second company, Bright Pages, Jess faced a ‘new type of scary’. No longer naive to all that could go wrong, she struggled with ‘analysis paralysis’.

I couldn’t agree with her more that the key to conquering fear before you do anything new is to apply the data and research you’ve learned previously. Nerves can make you hesitant, but to me it means you’re on the right track. Going through experiences gives you confidence when it comes to pressing on the gas and seeing what happens.

Pretend To Go All In (9:15)

Jess spoke to us from Zion National Park inside the Airstream she and her husband have shared for almost two years after selling their home, packing all their belongings, and heading cross country to ‘chase the bright side’. The couple credits the lifestyle change and mantra they now live by – which is also the title of Jess’s latest book – to a coconut shrimp dinner.

Tip: Give yourself a time period of pretending to go all in. Create a list of what needs to be done and knock the tasks out one-by-one. After the exercise you might figure out that your big scary plan is a lot more doable than you initially thought.

New Problems = New Opportunities (12:58)

According to Jess ‘new problems are the breeding ground for innovation’.

Without the big obstacle of COVID she would have never discovered that the Headbands of Hope team could produce facemasks. Face masks were never on her radar! But with new problems come new solutions! Her team ended up donating over 100,000 masks to hospitals across the nation.

The same situation occurred when she started experiencing anxiety being a business owner, juggling COVID, and trying to be all things to all people. To help battle her anxiety she started journaling. She quickly realized that others might also benefit from this simple strategy. Thus the birth of her newest venture – a journaling platform called Bright Pages.

Reminds me of the cheesy (but true!) quote that in order for a bright rainbow – you need some heavy rain!

Dealing With Imposter Syndrome (16:22)

When trying to find our voice we sometimes (ok maybe all the time!) doubt our skills and fall victim to the worst enemy…comparison. Oh yes the green monster of jealous shows up every time you don’t want them to. And who can forget their annoying cousin, Imposter syndrome? We have all of these characters swimming around in our head and they keep us from speaking our story. Jess’s point here was HUGE: “We don’t always have to have some grandiose story about “climbing Mount Everest” people want to see you’re human. And your story relates to them.”

Many of us feel that we need to come across as credible (and extremely qualified!) to our audience to take something away from our message. Jess shared that shifting the focus from being credible to being relatable is key. ‘People want to connect the dots from where they’re sitting to where you’re standing.’

First Time Speaking Advice (22:58)

Amazing you’ve decided that you want to share your story. The inevitable next question is, ‘Where do I start?’ Here’s Jess’s best tips for getting started with Public Speaking:

1. Use local and virtual speaking events as a less daunting starting point.

2. Input a contract clause for testimonials and referrals as a way to offset costs and build a repertoire.

3. Prep your speech with bullets and subpoints to create memory triggers rather than writing out your whole speech.

4. Know that ‘the audience is on your side.’ We’ve all witnessed the embarrassment of clamming up on stage. When you know the audience is rooting for you to win, your demeanor changes and confidence takes the place of insecurity.

Tip: Forget the advice that you should picture others in their underwear! It’s gross and weird. Ha!

How To Create Content That Cuts Through The Noise (29:05)

The key to creating content that cuts through the noise is to create the content you want to consume. When you stop scrolling, think to yourself, “Why did I stop on this?” “Was it pretty?” “Was it quick?” “Was it helpful?” Think about why you are making the decisions to consume.

Jess lives by the rule, ‘Simple, yet significant’ and I couldn’t agree more!

Who Does Jess Learn From? (33:35)

Living as a student means you’re always learning. Mary Marantz, Natalie Franke, and Britney Janine are among Jess’s top three influencers currently. She also credits LinkedIn courses, Pinterest Lab, and World Class Assistant to helping her grow professionally.

Speed Round Questions (39:55) 

• What have you started doing or using lately that you love? The 28-day meditation challenge on Sam Harris’s Waking Up app which helps me to be more present. I’m on day 18!

• What do you wish that you had more of right now?  Wi-Fi. I would love more access to internet while living in an Airstream.

• What’s the best gift you’ve given yourself this year? Mountain biking lessons. I am sharpening my beginner’s muscle, learning to be ok with not being good at everything.

THIS WEEK’S HOMEWORK: What should we begin to do this week?

Listen to Business on the Bright Side on Apple podcasts, take my public speaking course on LinkedIn, and go live on the platform you’d like to grow on for two to three minutes. Flex that beginner’s muscle and share what you have to say.

Next week:

Dan Schawbel is teaching us about how to prep for the 2021 work environment. He’s a New York Times bestselling author and an expert on workplace intelligence. Join us here to get all the latest predictions on the year ahead.