It seems like everyone wants to be a coach these days, including yours truly.
It’s not just my opinions: numerous other people have posted about the coaching trend. The New York Times even did a piece about the pyramid scheme nature of life coaching. This piece got so much attention that it spawned a 40+ (and still going) Slack thread in one of my coaching communities.
So, why am I jumping on the coaching bandwagon?
My journey with coaching
I was exposed to coaching early in my career. As a Google APM, we all got executive coaches, even though we were still understanding what it meant to be a working adult. At the time, Google worked with a coaching company, and we could pick (and switch) coaches as many times as we wanted.
After some trial and error, I found my coach Andrea. She was the right balance of empathetic and action-oriented, with a side of tough love. When I left Google, I negotiated Thumbtack to pay for her services, along with every startup/company I joined after.
Through Andrea, I became more assertive through understanding the difference between arrogance and assertiveness. I learned to manage challenging stakeholders. I learned to advocate for myself. And all of this led me to build more confidence in myself.
Seeing this transformation (and its impact) over many years made me think: how cool would it be to do this for others. This feeling only intensified when I became a people manager, and saw the first-order impact of continuous support in other people’s growth.
Getting Started
In January 2023, I launched my coaching business by filing for an LLC and building my website. I had been mulling about it for two years and wanted to finally take some action. I decided to operate in “stealth” mode, sharing my new venture with people in my network, mostly because I wasn’t sure if it’s something I wanted to do. Or if I’m being honest, I wasn’t sure if I’d be good at it.
Like many other coaches, I started by offering free sessions, mostly to friends. I built my skills, got some testimonials, and then took on paid clients at discounted prices. I was still working at the time, so I didn’t need it to support myself financially. Instead, I wanted to know: do I like this? Does it energize me?
The short answer is yes. The long answer is yes and no. Building genuine connections, creating unlocks, and seeing results is some of the most heartwarming, fulfilling, empowering things I’ve experienced in my life. I’m grateful that within a year, I was able to work with 15+ people, landing wins like new jobs, product roadmaps, and/or career clarity. I also love the idea of building a business, especially the flexibility and ownership that comes with it.
But being a coach is so much more than that. It takes a LOT of work to find the right clients that you can help (and want to work with you). There’s so much administrative stuff (invoicing, scheduling, followup emails, etc.) You have to spend a lot of time marketing, which isn’t something that I’m naturally skilled/good at.
On the financial side, coaching is a pretty volatile gig. Some months, I’ve made a decent chunk of change. Other months, it’s been $0. As a W-2 girlie, the volatility is scary. Plus, it’s not like there’s a lot of disposable income in this economy, with constant layoffs and inflation.
So at the one year mark, I had to ask myself: is it time to go all in? Or fold?
Going all in
The decision came down to three questions:
How much do I love the idea of building a coaching business, despite all the challenges?
What’s my tolerance for risk? Is there a way to derisk my path?
Do I want the growth that will come from taking on this challenge, even if I fail?
The answer, for the above, is a yes. I’ve spent a lot of time thinking and learning about mindfulness, careers, and transitions. I’d love to use this knowledge to empower others. More importantly, I see this work fitting into my new mission to empower people by raising awareness and expanding possibilities. That being said, there is a financial risk with this decision since most businesses fail. So, I’m exploring ways to de-risk this path.
I also think the skills required to build this business will help me in my creative endeavors. Turns out, movies and TV shows are really just small businesses under the hood. Getting better at clarifying what I can do, branding myself, mentoring/coaching others- these are transferable skills for writing/directing/producing (or even going back to a full time role).
Regardless of whether I fail or succeed, the learning will be valuable.
The rebrand
I spent the last three months synthesizing my learnings from a year of coaching to realign on who I wanted to work with and how I wanted to help them. Through lots of conversation and support, I narrowed down my initial offerings down to three:
💡 Pivot into Product: providing high-touch, personalized coaching to land folks a fulfilling, high-paying product role.
📌 Develop strategic leadership: help folks pivot from an execution-oriented PM to one that has strategic impact at their company.
✨ Design Your Career: using mind and body signals to help folks design an intentional career next step, inside or outside of product.
Then, I worked on my website, pricing, and go-to-market strategy, doing things like iterating on my website copy, brainstorming growth experiments, and setting revenue targets. I loved the process. It was so satisfying to apply my PM skills to build something of my own.
On June 3rd, I officially launched my new website, as well as updated LinkedIn/Substack/Twitter profiles. This was (is?) terrifying. No matter how much work you put in, it’s always scary to put yourself out there. But I know that growth involves doing things that make you uncomfortable, so I’ve learned to accept the discomfort as par for the course.
I’d love your support
I know I can’t do this alone, and I’d love your support in this journey. Here’s how you can help:
Share my website with one person in your network who could benefit from my support. The initial consultation is free!
Tag a friend in the comments who might be interested in working with me.
Like this post (or comment) to spread the word.
PS- happy 25th post! Thank you for following me on this journey. I appreciate every single one of you <3
Thanks for reading
I’m on a journey to share the messiness of my career transition into a creative & entrepreneurial career, while also reflecting on the hard-won lessons from my product career.
If you want to see more content like this, heart the post. Better yet, share it with a friend!
Hearing from readers also gives me a ton of energy. Drop a comment if you have questions about my journey into coaching, or if there’s other coaching-related content you’d like to see.
If you’re looking to pivot into product, figure out your next career move, or become a more strategic product leader, I’d love to support you as a coach. Book a free consultation to start the conversation!
Awesome
Any new journey is hard along with lots of fear of unknown
But each journey begins with a step which you have taken
Let us take one step at a time and before you know you will be at your destination
Meanwhile enjoy the journey
Good luck and lots of good wishes
Congratulations!! I wanted to share an idea to address your less desirable jobs to be done like client sourcing and administrative work, my company BetterUp takes care of all that as a coaching platform solution. Many coaches contract with us and also do their own business or other coaching platforms too.