Eighteen months ago, I took a leap from product leadership in tech and signed up for a coaching certification via Hudson. I’m in the messy middle of building my first business (they say it takes 2-5 years) and here is an update on how it’s going
Business Development
💁🏼♀️Target customer - My clients continue to be leaders in big tech, emerging leaders in a variety of industries (front-line managers, high achievers, etc.), and women seeking to be better seen for the impact they are having and/or transitioning to new adventures. I also tried to reach out to the young parent sector across industries, but that didn’t work (yet). My hypothesis is that this group of people is so busy that focusing on themselves is hard to prioritize in this season.
🎉 Expansion of offerings - I’m a certified Enneagram practitioner now, having completed my IEQ9 accreditation earlier this summer — it’s been a good addition to my coaching toolbox, and something I’m excited to bring into more organizational trainings. I’ve been offering mini sessions (Enneagram assessment + 2 sessions) to those who’ve never had a coach, to get a sense of what it would be like, and I’ve had good success there. I’m thinking about doing my next training next year (I have a goal to do one training a year) - continuing to focus on team coaching and facilitating.
👾 AI in my business - no post would feel complete without touching on this. AI has been helpful to me as a pseudo business coach - helping me write a business plan, debate my pricing offers and give me structure since there is so much that can be done in the space of business development. It has saved me time so that I can put off hiring an assistant for a bit longer, though that day is coming.
💡 Biggest learning so far - the logical part of my brain says that I need to do a lot of social content, coaching offer experiments, website updates and cold networking to get more clients. In reality, most of my business is coming from people I’ve coached recommending me to others they know. Thank you to my community for showing up for me in this way - it means everything.
Lifestyle Job vs. the Tech Grind
To name the obvious, I have chosen to pen a chapter of my career where I am not building products and am not employed by a tech company. I don’t feel that my time in tech or as a product leader is over - it has been interesting to reflect what it’s been like to take a turn off that road.
James Clear had a line recently that stuck with me — the real question isn't "can I achieve this," but "What am I really trying to accomplish here?" Because sometimes the honest answer isn't the promotion or the book deal. It's just a life you enjoy — and there are many versions of that.
So as I build this version of the life that I enjoy, here is what I am seeing:
❄️🌼🌞🍁 Coaching is seasonal and it aligns well to my priorities right now. I have seen an influx of business September - November and January through May. With my greater emphasis on spending time with the kids, this has allowed me to have a more enjoyable summer without the pressure of a different camp every week. I did not know how much joy it would bring me to have slower mornings with my kids when they are off school.
📈 Effort directly correlates to new business - the unfortunate truth is that business and progress only get made when I put effort into it. So my general benchmark is to spend as many hours in a week doing business development as I do coaching. Additionally, at a minimum, I try to do one thing a day to grow the business.
🎉 My life is fuller than ever with everything else that now fits - I’m so grateful for this chapter of my life. I have gotten to say yes to things that I couldn’t have before. I have learned a sport (tennis) and met a new community of women by doing it, I am more involved in my kids school communities than I ever was before (I can chaperone a week long camp for middle school and not feel bad about it) and I can focus on my health, which will set me up for a better for decades to come.
💡 Biggest learning - I thought that boundaries would be easier to set once I am not working a full-time corporate job, but in fact they are harder. Volunteer work does not shut off after 5pm or on the weekends the way work pretends to try to. Kid stuff goes on 24/7, and if a new business prospect comes out of the woodwork while I am on vacation, it seems foolish to ignore until “I’m back in the office” (at this stage of my business). Net/net - boundary setting continues to be an area of development for me.
Trends I’m seeing from clients
*Disclaimer - All coaching is confidential, so I will only speak in broad terms on this topic to preserve the privacy of my clients.
Many of my clients are dealing with existential dread that has veiled the tech industry and I’m hearing things I’ve never heard before like “I’m so glad I don’t work in tech,” from clients who aren’t in the eye of the storm.
While everyone’s journey is different, here are some of the questions that keep coming up in my coaching sessions across industries, titles and levels:
1️⃣ What additional skills should I pursue right now - on the job or through certifications/more schooling?
2️⃣ Should I stay in my current role because I have a job or should I look for a new one?
3️⃣ How do I position myself/add more value as an emerging leader (and not get left behind) in this time when there is a thirst for new ideas and big fresh energy?
There are no easy answers, though one of the things that has been helping in these conversations is to help my client identify where they are in the cycle of renewal. This is a Hudson Institute construct that gives language around going through change and ambiguity. If that’s you, I highly recommend the 5-minute video on the concept.
Overall, I’m happy with the business momentum that I am getting and grateful for the clients I’ve had the chance to support and walk alongside. This hasn’t been easy or straightforward and at times, it’s a little bit lonely, but I’m learning so much from building a business and I’m loving the work and the flexibility it gives me.
I’ve got some wonderful people locked in for the fall, and I have a few spots for September.
If any of these questions are the ones keeping you up right now — or you know someone wrestling with them — hit reply. I'd love to talk.
Thanks for being in my corner, and enjoy the rest of your summer!
— Helen