life’s too short not to sing 🎤

what karaoke taught me about side hustles and why you shouldn’t wait to start. (#406)

“Today is where your book begins, the rest is still unwritten.” ✍🏾
~Natasha Bedingfield

Last week, I finally crossed something off my bucket list — karaoke! 🎤

For close to 10 years, I told myself, it would take several tequila shots to get up there. But in reality? All it took was a supportive group of friends, a couple of cocktails (because, let’s be real, have you met me?) and the right songs to get the crowd going.

Standing in front of that karaoke screen, mic in hand, my heart was racing, my palms were sweaty, and for a second, I wondered if I should just back out.

I was nervous. That mix of anxiety and excitement - my friend Saya calls it “nervou-cited” - was intense. But then, I took a deep breath and started singing Natasha Bedingfield’s “Unwritten”. Then came a “Love Shack” duet. And finally, I closed with Pink’s “Raise Your Glass”.

No, I didn’t suddenly become a musical star. I missed a few notes, got the timing wrong, forgot how that part of the song went entirely and ran out of breath many times. But none of that mattered.

What mattered was that I showed up, stepped outside my comfort zone, and gave myself permission to be imperfect and fully present.

Here’s what hit me as I reflected on that experience: side hustles can work the same way.

At times, we let the idea of perfection keep us from starting things we really want to do.

(I say this as a recovering perfectionist. 🙃)

But all we need is:

• A little cheerleading

• A supportive community

• The willingness to try.

If you’re asking “Well, Jess…why karaoke? Why now?”

A few months ago, I attended three funerals in two weeks. It hit me hard and forced me to ask myself:

What am I waiting for?

Life is too short to stay stuck in “someday” mode. When I close my eyes for the last time, I want to know that I lived a life with no regrets.

Your side hustle doesn’t need to be perfect to be meaningful. It just needs to exist.

It needs you to show up, choose your song, and start singing—even if your voice shakes a little.

Here’s what my karaoke adventure taught me about starting anything new:

• The right environment matters. I sang with people I felt safe with —just like how finding a supportive business community (like this one!) can make all the difference. We even started the night with a group number, singing “Seasons of Love”!

  • Relatedly, I spoke to a friend who did karaoke once with a group of people who didn’t support her because of the song she picked (jerks!), which led to a really bad experience, and she didn’t want to try it again. The people around you matter so much when you’re doing something vulnerable — whether that’s singing in public or launching your side hustle. Find your people who’ll clap even when you miss a note.

• Starting messy beats not starting. Those missed notes? They’re like your first newsletters or social media posts —awkward but necessary. No one remembers the mistakes; they remember that you showed up.

• Having a buddy helps! (Thank you

  Christine Mortensen
  , for singing “Love Shack” with me and for documenting my Raise Your Glass performance!) Business, like karaoke, is way more fun when you have someone to partner up and brainstorm with.

  • Not to mention, the night (and a preceding Karaoke 101 sesh) was organized by the fabulous Lindsay Griffith!

Your turn: What’s your “karaoke moment” in your side hustle? That thing you want to do but keep putting off?

Could you take just one baby step toward it this week?

Hit reply and let me know—I’d love to cheer you on.

On to the picks! ✨

P.S. If you’re thinking, “but I’m not ready,” that might be exactly why you should start. 💕

P.P.S. If you’re looking for a buddy to help you with your side hustle, I gotchu. Reply and let’s chat.

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#picks 😍

📺 Something I watched:

I’m rewatching Hallmark’s The Way Home and finally diving into season 2. Three generations of strong women, a touch of time travel, and the journey of, ahem, finding your way home - chef’s kiss.

🌟 Something to try:

Social media is a bit of a hot mess right now, so I’m stepping away and getting back to watching TV, reading (my friend Brandy just recommended this! and I am loving this super chill book club). I also have a couple of jigsaw puzzles waiting for me.

Sometimes the best thing to do is step away from the noise. Here are some other ideas…

162 things to do instead of doomscrolling

👩🏽‍💻 Something from the community:

Connie, a fellow side hustler, shared that she made some real progress in the last couple of weeks by alternating 30-minute work sessions on Cave Day (think guided focus sessions) with 30-minute workouts. Proof that baby steps really do add up!

📚 Something I’ve been reflecting on:

After singing, I felt exhilarated and deeply relaxed. Singing helps regulate your nervous system—no wonder I felt so good! Sometimes, the things we fear most are the ones that bring the most joy.

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#icymi

• 😍. Last issue’s top pick: 6-minute video on simplifying your life (second week in a row!)

“There will be an answer, let it be.” 🕊️ ~The Beatles

• 🌱 Side Hustle Idea Kickstart: Stuck on what business to start? This mini-course gives you six bite-sized lessons plus personal feedback from me!
  

• 💡 For my Chicago folks!

  • My friend Vanessa is hosting “She Figured It Out!”, an empowering IWD brunch (Mar 8) where women share their health journey wins. Inspiring speakers, good food, and great connections in Lincoln Park!

  • Help rescue dogs by betting on love! 🌹 Vote for Bachelor contestants & support Mutts of the Midway. No need to watch the show - just help Chicago pups find homes!

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#lifevibes

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#supporters ☕️

Thank you, Kelly, Melinda, Tawanna, Gia, Lori, Ayana, Krista, Jessica, Annetta, Constance, Tunde, Jen, Michelle, Emile, Bex, Kim, Angela G., Lauren B., Chelsea, Amy, Ricky, Kirsten, Vin, Julie, Nicole, Hmza, Greg, Kristin, Kirstyn, Jess, Cheryl, Krysta, Adrena, Vidya, Kristyn, Danielle, Keyn, Terry, Vanessa, Meredith, Lauren, Meg, Maria J., Chivon, Kim, Luciano, Colie, Chasity, Laurie, Latienda, Collette, Anne, Kristen, Liz, Katherine, Monale, Betsy, Melissa, Lindsay, Jennifer, Kayla, Madison, Rae, Stephanie, Christine R., Christine M., Frances, Hannah, Chris, Brandy, Mea, Kristian, Maria K., Avery, Adam, Barbara, Shenee, Desiree, Lisa, Kandice, L’Oreal, and LaVerne for being #jesspicks supporters!! ❤️

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