Career planning: are you a pro or an amateur?
I've always been an amateur, but that's not a good strategy in 2025.
I've had a great career, but if I'm honest, my actual career planning has been quite amateur.
I've always worked hard at my job. I’ve never been less than 100% committed (you don't survive 5 years at Amazon by just turning up and working out how to use the coffee machine.)
But when it comes to actually sorting out my career, I realise now I left a lot to chance.
- I stuck around at the Guardian for too long
- I didn't learn half of what I could during my time at Amazon
- I knew during my time at Sky that I wanted to move on from media - but I did little to plan or prepare for that.
On the measures that really matter - my happiness, relationships and finances - it's worked out fine. But like many, I stumbled from opportunity to opportunity.
This is great for me as I get towards the end of my career. But, I wouldn't recommend it as a strategy in 2025.
The world has changed
In today's (and tomorrow's) product market, that amateur approach doesn't work.
The talent pool is deeper and more competitive than ever.
The expectations of what a great product person needs to achieve have progressively ratcheted up over the last decade.
Every product role has 100+ applications within hours of posting, our experience is assessed in a nano second by some algorithm. AI is transforming how we work and what we work on.
And as you get older (ie: from mid 30s), more senior, and your financial needs tend to be greater - it only gets tougher.
I've rarely met a product manager who isn't passionate about what they do; and keen to both learn and improve.
But I've also met a lot who like me, take their job seriously, but are decidedly amateur about their career planning.
It's time to turn pro.
Lessons from 'The War of Art'
This pro-am division hit me this week as I was reading Steven Pressfield's "The War of Art." Which is a brilliant polemic against 'Resistance' which he describes as ' the most toxic force on the planet' .
Reistance is what stops writers writing their novel and enterpreneurs from starting their businesses. It keeps people in jobs when they've long since stopped growing; and makes sure that the Peloton that was going to get you fit ends up as the world's most expensive clothes stand.
Resistance affects everyone. But professionals deal with it.
There's no voodoo involved. No cute habits. Just doggedly getting on with the job. These are some of the attributes he gives professionals.
We show up every day.
We show up no matter what.
We are committed over the long haul.
The stakes for us are high and real.
We master the technique of our jobs.
We have a sense of humour about our jobs.
We receive praise or blame in the real world.
Reading that, I realised I'd been a professional product manager for decades, but an amateur when it came to planning my career.
What Amateur Career Management Looks Like
Amateur career management is reactive.
It's knowing that your LinkedIn profile is a bit crappy but you'll sort it out some time.
It's letting yourself develop Achievement Deficit Disorder, but not asking why and doing something about it.
It's getting so caught up in your job that you lose sight of where you want your career to go, and what you're doing about it.
It's getting a rejection and thinking you're better not trying.
It's about losing a sense of what's really valued in the market - and making sure you are offering it.
It's about having a decent salary, but no long term financial plan.
It's not bad. It's not lazy. It's natural given the thousand things we all have to do.
It's just - to use the understatement I heard a hundred times a day at Amazon: sub-optimal
At times, I have done all of the above.
At Sky, I had a great time on many levels. Loved the people, the products we were working on, and was handsomely rewarded. We also shipped a lot. But I totally lost sight of the product world that was changing rapidly on the outside, and didn't see how I was slipping behind.
When it came to looking for a next role, I found I was nowhere near as 'hot' as I thought I was.
A total amateur error that resulted in months of often painful job hunting.
What Professional Career Management Looks Like
Professional career management starts with showing up consistently. It means working on your career whether you feel like it or not, whether things are going well or badly.
It means having a plan - not a rigid 10-year roadmap that will look irrelevant within six months, but a clear sense of what you're trying to achieve over the next 12-18 months and why. It means regularly assessing where you stand, identifying gaps, and taking deliberate action to address them.
It means building and maintaining relationships before you need them. Not cynical networking, but going out your way to connect and keep in touch with people whose expertise (and often friendship) you value.
It means keeping your skills current and your market knowledge fresh.
It means documenting your achievements and being able to articulate your impact clearly.
Most importantly, it means not over-identifying with any single job or company.
Your career is bigger than your current role, and professional career management requires keeping that perspective even when you love what you're doing.
Three Pro Tips
If you recognise yourself in the amateur description, don't worry. It's natural. I've been there.
The shift to professional career management isn't about becoming more corporate or strategic in a cold way. It's about respecting your career enough to manage it properly. Here’s three things you can do to kick things off.
Set yourself some career OKRs (more on that next week) set aside time monthly to assess progress, quarterly to review your plan, annually to think about bigger strategic shifts (if you need help with this reply to this email saying ‘OKRs please’).
Find 5 companies that you want to work for . Find out everything you can about them, and then have a focussed effort to get on their radar (here’s a playbook for how to do it from Ben Erez)
Every week, capture your achievements at work. Everything. Pendo’s Dave Killeen suggests using Chat GPT to store everything and then let it resurface back to you (tell it to create an Achievements project and explain what you’ll be using it for). But even just dumping everything into your Notes is fine. Give yourself a monthly appraisal (make it part of your personal ‘strategy offsite’ at the local coffee place while also looking at your OKRs!). Are you feeding your CV, developing your skills - or just standing still?
Get comfortable with the fact that professional career management sometimes means making decisions that don't feel good in the short term but serve your longer-term objectives.
And finally a plug: if you think this is relevant/ useful..you're welcome to kick off your new professionalism with a free assessment against my Vital 9 framework.
Everyone I've tested it on so far has found the process useful..an for now the assessment and a 30 minute debrief is free. Just reply to this email with 'yes please' in the message.
Next week: using OKRs for your Career.