My Second Career Reset: Thinking Two Moves Ahead This Time

I posted this on my LinkedIn too, in the hope someone will read it and give me a million dollars - is that you? This week we're thinking out loud and writing about my second career reset...

I’m in the middle of my second career change. After shifting from graphic design to brand strategy / agency planner, I'm now pivoting from agency to marketing.

From planner to CMO... Bit of a dive into the deepend, I admit.

I've noticed the 'thinking out loud' posts I shared on Linkedin are going really well, with good reach and lots of people DM'ing me (actually) - so it spurred me to give it a go with another article thinking out loud on how this career pivot/reset/switch/change is going.

Why Change Careers, Again?

Work futurists and HR experts have been saying for as long as I can remember that all of us need to be thinking about 'lifelong learning' and seeing our career as a series of careers, the 'job for life is gone'.

But I'd hazard a guess that for most, that sounds hard, scary and undesirable - most of us imagine a career trajectory that mostly comprises promotions; more money, influence and title. But mostly still within the same domain, realm or capability.

The truth is I wasn't looking for this change, it found me. My job at Howatson+Company was brilliant, the agency was running hot, I was happy and content.

But the opportunity was too good to pass up, with lots of downstream opportunities to go in a myriad directions. When I looked ahead to the agency career, there was really only one direction to go, and honestly, the job of an agency Chief Strategy Officer didn't look appealing, at all.

Oh, also... Ai - must mention artificial intelligence! The joke I've been making is I've switched from worrying about competing with Ai, to becoming a buyer of Ai. Its a cute one-liner but also true. The last end-of-year review at H+Co had a huge emphasis on Ai, and the implications were clear. The agency, industry and indeed world was being reshaped by Ai, and I didn't exactly like the direction of travel.

The first time I didn’t even realise what I was doing. Despite this being unplanned, this second time I knew exactly what I was doing, and how to apply the lessons from the first one, to accelerate the success and impact I could achieve with the second reset.

Learning From My First Reset – Walking Blind

I went from being a designer to a planner without much of a strategy (lols). Like stumbling into a new room than stepping confidently through a door.

There wasn't a lot of forethought to it than I'd become bored of design; choosing fonts, colours and grids, drawing logos.

I was interested in working upstream. I moved from Designworks into a planning role at Marcel simply because I wanted to be closer to the idea. I didn’t think much further than that.

That was about as deep as the thinking went - no grand theories about 'where the puck was headed' in terms of the future of the industry.

I didn’t come into it with intention.

No research, understanding or planning on how to quickly develop the skill set. I didn’t know the language. I didn’t build a network or look for mentors. I just showed up and tried to figure it out on the job .It took longer than it needed to. I treated the transition like a job change, not a career evolution. The result? I played from behind. Always catching up. Always reactive.

It worked, eventually. I grew into my role at Marcel, was very lucky to get an opportunity at CHE Proximity, and then followed many dear colleagues to Howatson+Company.

Looking back, it wasn't until H+Co that I really felt like I understood what the job of a planner is, and could see how you build a career in that space.

Just in time for my next move - leaving the industry!

The Second Reset – Leaning into Learning and 'Lily Pads'

This time around, I’ve approached the career shift with a very different mindset, I’m not guessing. I’m building with intention.

Instead of reacting to the opportunity in front of me, I’ve stepped back to consider the longer arc of where I want to go and how I want to grow. I’m not thinking in terms of job titles or companies - I’m thinking in terms of skill sets, learning cycles, and momentum.

I’ve made a conscious effort to upskill quickly and broadly. I’m learning how to structure and scale paid LinkedIn campaigns. I’m getting deeper into how B2B funnels actually function. I’m experimenting with AI tools for sales enablement and marketing content—trying to understand where they’re useful, and where they still fall short.

I’m building a better understanding of how HR teams think, what problems they face, and how our product at Mumba actually supports their world. I’m spending time with the engineering team, understanding the tech stack, product limitations, and roadmap.

I'm getting exposure to our board, the startup and venture capitalism ecosystem.

This reset is also a mindset shift. I’m no longer focused on being the smartest voice in the room. I’m focused on being the one who learns the fastest.

More importantly, I’ve started to see this role as one step in a longer path. I’m not aiming to “arrive” at a final role—I’m building toward something with more flexibility, more leverage, and more impact. Long term, that might look like working in early-stage tech, investing in startups, or supporting founders in a more hands-on way.

But right now, I’m focused on doing the work. Learning, applying, testing, and refining. Making sure this lily pad is as strong as it can be—because what I build here will shape the next step.

Career Moves As A Series of Lily Pad 'Hops'

The lily pad analogy is something I’ve found myself using a lot in conversations lately. It’s a simple way to visualise what a thoughtful, long-term career shift looks like. Instead of aiming for a perfect leap from your current role to your dream job, you look for the next stable landing spot. A place to build, to learn, and to get closer to where you want to go.

You’re on one side of the river. Your dream job is on the other.

You don’t leap straight across. You land on Lily Pad One.

That might mean going into an unglamorous industry or taking a step back in title. But it gives you proximity. Capability. Credibility. A way to leverage the experience you had in an agency job, but accrue experience relevant for where you are going.

Then you move to Lily Pad Two. Something that lines up with your long-term direction. Different domain. Closer culture fit. A stronger link to the work you actually want to do.

In the example I’ve shared with friends:

Say you want to be the CMO of a surf brand. Your first pad might be in a less glamorous space - something like financial services or a B2B gig. It may not be exciting, but it gives you control of a budget, exposure to performance marketing, and ownership of the full marketing function.

That’s where you learn the fundamentals. That’s where you get strong.

Then you look for your second pad. You've got the fundamentals and some experience down as a marketer. Now, you've got permission into marketing for a consumer-facing product. Maybe it’s ecomm. Maybe it’s a smaller brand with a stronger link to your personal passions or lifestyle. That role puts you in the same world as the job you eventually want—and makes you a natural fit when the opportunity arrives.

Two hops, and you're ready to snipe your dream gig.... right? Or maybe there isn't a dream gig in mind, no destination - now I'm starting to really appreciate the cliché: it's about the journey, not the destination.

That’s the mindset I’m trying to keep front and centre. Not evaluating if this is the perfect job, but focusing on strategic progression. Each move doesn’t need to be forever. It just needs to build the skills, relationships, and context for what comes next.

Career Growth as Compounding Momentum

The more conversations I have with peers making mid-career transitions, the more I hear a shared truth: we’re all just trying to find the next strong step. Not the dream role. Not the forever company. Just the move that strengthens us for the next one.

Careers aren’t linear. They’re not ladders. They’re more like rhythms. Build. Land. Grow. Leap. And repeat.

It’s a pattern that rewards patience, strategy, and learning over ego, speed, or aesthetics. It’s also one that makes room for reinvention—because you’re never locked into a single identity. You’re always in motion.

What Comes After This Reset?

This second reset has taught me to think like a builder, not just a contributor. To focus on developing durable skills and flexible thinking. To embrace discomfort as a sign I’m growing, not failing.

And while I’m committed to doing great work in my current role, I also have one eye on the horizon. What comes after this lily pad? If I zoom out, the answer is clear: I want to eventually move into early-stage investing.

VC life baby!

Whether that’s as a venture partner, angel investor, or advisor to founders - I want to use what I’ve learned to support others who are just starting out. I like the idea of backing ambition. In helping new ideas get off the ground.

And in sharing the hard-won lessons of reinvention, growth, and momentum. That’s the future I’m building toward. Two moves ahead. And always thinking about what I’ll need to build when I land.