The Plan
Step 7. How can I ensure a successful, sustained life change?
If you haven’t read them already, you might want to start with:
Sorry for taking last week off. (Be honest, you didn’t notice, did you?) Instead of climbing metaphorical mountains, I was climbing real mountains.
In the final step of Strategize Your Life, you pull everything together into an overarching plan using OKRs (Objectives and Key Results). For each thing you committed to in Step 6, you:
Define an ambitious high-level Objective. For example, climb every mountain in the High Pathways book.
Break each Objective into a few specific, measurable, and time-bound Key Results. For example, climb Mount Warner with Dee and Sam in April 2026.
Follow goal-setting best practice: share your plan, set incentives, celebrate progress, and regularly review and refine your approach. For example: Climb Mount Technical and Mount Princess instead of Mount Warner, because the pesky Rakaia River is too high to cross.
What I like about OKRs is that they give you the freedom to be bold and adventurous with the Objective, while forcing you to stay precise and accountable with the Key Results.
Anyway, you might remember that a couple of weeks ago I went off-piste and used Richard Rumelt’s Diagnosis → Crux → Guiding Policy framework for Step 6 of Strategize Your Life. The big takeaway was that of all the things I could work on, the most important was getting back into meaningful work.
Conveniently, Rumelt’s framework ends with a “set of coordinated actions.” So ChatGPT had already jumped ahead and completed Step 7 for me, producing a ‘Find a Dream Job’ plan.
Unfortunately, it was generic, jargon-filled, and a bit… meh. There wasn’t an OKR in sight.
But it pointed me in the right direction: treat my job search like a pipeline. Get clear on what I’m good at and what I’m looking for. Then set targets. Send the emails. Have the conversations. Track activity. Review progress.
This approach helped me realise that I needed to focus on the process. After all, I can’t control whether a role exists, whether I will find out about it, whether a recruiter thinks I am a match for the job, who else might be applying, or a dozen other variables. All I can control is the process. If I’m clear about what I’m looking for and consistently tell enough people, eventually those seeds will germinate.
How to Find a Dream Job in Five Easy Steps
Here’s what I did in a bit more detail:
Spent the time to accurately describe ‘the ask.’ I wrote a short, punchy email describing what I’m looking for and what I’m good at. Something easy to skim. Easy to forward. Hard to write.
Hi [name], trust the year has started well, it’s been a while!
I’m hoping you might do me a favour. After a season where I’ve prioritised the kids, it’s time to get back into work. Do you know anyone I should speak to about senior roles (CEO/COO/CPO/CCO level), or a good recruiter? I figure you’re pretty well-connected!
No worries if no one comes to mind, but here is some boilerplate to forward if useful:
What I’m looking for in a nutshell:An organisation with a meaningful mission and a great team, with hard (interesting! juicy!) problems to solve. I want something that stretches me
Ideally something Wellington-based (although I’m open to travelling 1–2 days a week)
What I’m known for:
Product / customer (I founded a UX research consultancy, was Chief Product Officer then Chief Customer Officer at Trade Me)
People stuff: inspiring teams (largest was ~130 people), managing managers, shifting culture, building community
Like all senior leaders, I am very experienced at setting strategy, but I’m at my best when executing. It’s my favourite
Being curious and asking thoughtful, unusual questions
How I’m different:
Four-time founder (2 successful exits, 2 failures) + start-up investor and mentor → I bring a bit of entrepreneurial mongrel to whatever I do
Experience across start-up, scale-up, corporate, professional services and not-for-profit
Breadth across business functions: tech, product, UX/research, contact centre, comms, marketing, community, trust & safety, sales, etc.
Thanks heaps, appreciate you giving it a think!
Trent
P.S. I’m open to directorships too, just started as a director at Dot Loves Data - do you know them?Exported all my LinkedIn contacts and tagged people who I thought might be able to help. Because I have 4,472 LinkedIn contacts I didn’t just eyeball them, I tried to slice and dice based on where they lived, job title, industry, etc. ChatGPT helped.
Each Monday, I emailed 10 people from the LinkedIn list. I could have gone much harder here—I recently read in Andy Budd’s excellent Growth Equation that the founder of Intercom would email 100 potential customers a week!—but I didn’t want to go too hard because my intention was to…
…Have 3-5 in-person conversations each week. Coffee. Beer. Lunch. This was lovely, I connected with a bunch of people I hadn’t spoken to in years and met a lot of new people (mostly recruiters who had been recommended to me).
Finally, I also researched potential employers (thanks to ChatGPT’s Deep Research mode), and approached some of them directly. I’m still working through this.
How it’s going?
Did this process actually work? Did I find a job?
And was Strategize Your Life worth it?
All that and more next week, when I’ll pull together all seven steps and reflect on the whole process. Stay tuned…