“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

Vote for a topic here.

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!

---

Note: This email may contain affiliate links. If you click through my link and make a purchase, I may receive “thank you money” at no additional cost to you. I only recommend products that I use and love.  

---

#sponsor

Ready for a change? A tech career could be your ticket to a rewarding future with an excellent salary and growth potential. Take this FREE quiz from CompTIA , the most respected place to help people launch and succeed in a tech career, to find out if a career in IT is right for you!

---

#loves 😍

• 🎧. 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.

---

#reads

You’re Doing a Great Job (YDAGJ)

“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.”

—

4 Questions Smart People Ask About Side Gigs (So They Don’t Lose Their Jobs)

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:

1. Are side hustles allowed?

2. Could it be a conflict of interest?

3. Do I have to tell my boss? Or HR?

4. 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.

---

#icymi

• 😍. Last issue’s top pick was: 525+ Places to Pitch Trello board

• 💬. Side Hustle Convos: Learn from others who have started successful businesses and are juggling it with their day jobs.

---

#classifieds 🗞

• Want to earn money promoting other newsletters and potentially pay to build your newsletter subscriber base? Join the SparkLoop Partner Network.
  

• Looking for audience-building or revenue-generating ideas? That’s why The Tilt was created 2x per week in your inbox … completely free. Subscribe now.
  

• This is the classified spot. Get your newsletter, tool, or event in front of 2600+ creators, side hustlers, and freelancers. Sponsor #jesspicks.

---

#lifevibes

---

supporters ☕️

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!! ❤️

Found this newsletter helpful?