“The patterns of our lives reveal us. Our habits measure us.” 📏 ~Mary Oliver
I could use your vote on a September training idea (#334)
Earlier this week, I recorded a podcast episode with Purse Strings about side hustles (Spotify version in #loves below). It was a 30ish-minute conversation, and I felt so re-energized by it. It was a reminder that I genuinely love this work of helping folks build businesses on their terms. And that my perspective is different from what you typically hear in this space.
I’m a big fan of starting small, experimenting, and being OK with keeping your side hustle a side hustle if that makes the most sense for you. The main reason I write this newsletter every week is to share my journey and things I’m learning in hopes that it will inspire you or that you’ll walk away with a new insight or tip for entrepreneur-ing YOUR way.
I LOVE talking about this stuff, and for the past few months, I’ve been thinking about my income streams and what makes sense for me, given all that I’m juggling and my capacity. Short and sweet, but impactful and can help several folks at once? This is why I’m adding speaking and facilitation gigs to the list.
For more income inspiration and because I’ve been curious about this for a while, I watched Josh Spector’s latest Skill session, where he talked about the business model for his skill sessions, live trainings he does every couple of months for his audience, where he does a deep dive on a topic and answers questions.
(If you are interested in watching it too, the training covers how to get started, market and promote these sessions, and how he sets them up. The price is $25 through tomorrow, then goes up to $50.)
After watching the video, I thought this could be a fun income stream that lets me do training/courses in a manageable way. Plus, I love the energy of live audiences. So I started going down the “how do you do subscriptions in Substack” rabbit hole and immediately felt overwhelmed. It felt too big. So I told myself, as I would tell my clients, “Baby steps, Jess.”
So instead of figuring this out for a whole year, let’s start with this. I’d like to do a $27 one-hour live training in September and would love to get your help with a topic. Here are a few I’m thinking about at a super high level:
creating a side hustle
how I do my curated newsletter
time management and productivity
finding self-care where you are
I’m pretty pumped about the idea of starting these and hope you are too. If I can get at least 10 votes on a topic, I’ll take another baby step forward next week!
On to the picks!
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🎧. Listening: Side Hustle Secrets: Building a Business on Your Terms with Jessica L. Williams. This one is a bit of a cheat as I’m listening to myself 😆 but I had a blast talking with Purse Strings about balancing your business with other commitments, not needing to become a full-time entrepreneur, starting small, and experimenting. Also added to the Side Hustla! Podcasts playlist featuring other helpful podcast episodes for juggling all the things.
📚. Tool: SaneBox. I was chatting with a friend about this earlier this week, so I thought I’d also mention it here. You might love this tool if you find it hard to manage your email. I’ve been using it for 2+ years, and it helps me focus more on my inbox and have newsletters go to a separate folder that I check when I have time. Give it a try and see how you like it, and you can get $5 off here.
“YDAGJ became our inside joke. Whenever one of us was having a rough day for any reason—big or small—we’d look each other in the eyes and fervently declare: “YOU’RE DOING A GREAT JOB!” It became a catchphrase, like a secret password, reminding us to calm down, to breathe, to stop being so perfectionistic and relentlessly hard on ourselves, and to celebrate all the wins in life—especially the tiny wins that often go unnoticed and unacknowledged.”
Before starting your side hustle, figuring out where your company stands on the issue is essential. So here are some questions you can ask before you start:
Are side hustles allowed?
Could it be a conflict of interest?
Do I have to tell my boss? Or HR?
How can I put my manager s mind at ease?
I have always preferred to be super transparent with my employer, but it has not always worked well. And it makes a big difference that your boss supports your life outside work.
😍. Last issue’s top pick was: 525+ Places to Pitch Trello board
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Thank you, 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, Keryn, 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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