Issue #011: Is it time to start a side hustle?

Hey Reader,

Welcome to issue #011 of The Next Chapter, a career planning newsletter for LGBTQ+ professionals.

This week, I'm covering:

A free webinar on whether a side hustle is right for you
Queer Career Consults IRL (and what’s next)
What to do when you feel stuck in your work
10% off gifted coaching packages

Let's dive in.

Is it time to start a side hustle?

I don’t know about you, but it feels like the past few years (COVID, mass layoffs, economic uncertainty, more chaos) have pushed a lot of people to question their career paths. Side hustles are looking more and more appealing as people reach for greater flexibility, fulfillment, and financial security.

I’m not here to give you business advice or tell you what to do. A side hustle may or may not be right for you, and that’s okay.

What I am here to do is help you think through whether this path actually aligns with your goals, your bandwidth, and the life you’re trying to build.

I’m partnering with Graphy to host a webinar on Wednesday, December 10 at 12pm PT / 3pm ET to help you think through questions like:

What’s really driving your interest in a side hustle?
What will it actually take, and can you realistically manage it alongside your current job?
How do you test an idea without going all-in?
What are the signs you’re ready to move forward vs. the signs you should wait?

Register for the webinar

Queer Career Consults IRL (and what's next)

Alex is sitting behind a table at a networking event with the sign "Career Coaching Corner" and smiling at the camera.

Last week, I hosted Queer Career Consults IRL for the first time at a big LGBTQ+ Holiday Networking mixer in San Francisco. The best part was having them at an event by queer people for queer people.

I've been doing the remote thing for nearly 6 years, which has allowed me to coach folks across the country (and even on the other side of the world). But it's a very different experience to sit and physically be present with someone to talk about the inherent messiness of careers.

I didn't do anything fancy this time around. Just a stack of business cards, a few little signs I printed at the local library, and an open seat for anyone who wanted to chat. It was all I needed.

It was a busy event, and I had the privilege of meeting a diverse cross-section of the community to talk about career exploration, job search, interviewing, and networking. Thanks to everyone who showed up openly and vulnerably.

One of my hopes for 2026 is to create more IRL experiences like this at events for the local LGBTQ+ community. If you're an event organizer or know of opportunities in the Bay Area, hit reply and tell me where I should head next.

When work just feels like a drag

Feeling stuck, lost, or disengaged at work is one of the most common things I hear from people. You know something needs to change, but you’re not sure what or how.

When your profession doesn’t light you up the way it used to, here are some ways you can start moving forward:

Lean into curiosity. Instead of forcing yourself to have all the answers right now, pay attention to what piques your interest. What are you drawn to when you’re scrolling online? What conversations light you up? What catches your attention when you’re out running errands?

Explore new things. Take a course, volunteer for a project outside your usual scope, talk to people in different roles or industries. Experimentation is how you figure out what resonates.

Take note of what piques your interest. Use a notes app, a journal, or even a voice memo to capture moments when something feels exciting or meaningful. Over time, patterns will emerge.

Clarity doesn’t always hit like a grand epiphany. It builds over time as you pay attention and take small steps forward.

Give the gift of clarity

10% off coaching packages when you buy one for someone else (through 12/31/2025)

If someone you care about needs help with career planning or the job search, I’m offering 10% off coaching packages to anyone who purchases one as a gift this holiday season.

Some of my past clients were in a tough spot when a friend or family member purchased a coaching package for them. It gave them the space and support they needed to clarify their goals and take action.

If you’re interested in gifting a coaching package between now and December 31, 2025, reply to this email and I’ll walk you through the options and next steps.

Explore coaching packages