Why You Shouldn’t Retire Alone and The 5 Tried And Tested Ways And 1 Brand New Way You Should Consider Keeping Your Retirement Journey Accountable
Often in our lives, we believe we’re unique. You are.
No one else on the planet has had the same upbringing, background and life experiences as you.
It’s often why as many of you venture into the next chapter of your life, you believe the best way to do it is alone.
But here’s the thing. We all need help.
As the old African proverb says…
“If you want to go fast, go alone. If you want to go far go together.”
And trust me, the next chapter of your life is a Marathon, not a sprint!
So, in this blog, I want to talk about the benefits of accountability and whilst some of these methods you can adopt and administer yourself and will be useful tools… I’m also going to explain why external accountability might be the best way for you to achieve the next chapter of life you truly want.
I’ve recently finished the What Happens Next book (feel free to take a look here if you’d like to join the waiting list) and this project has made me realise something really important.
No one does anything of consequence alone.
I’ve had support. I’ve had accountability. I’ve had people providing me with interesting ideas and asking me insightful questions. I definitely haven’t done it alone.
I’m not a fan of the ‘self made man’ fallacy. A story we often tell ourselves which paints a picture of our lives as entirely dependent on what you’ve done.
The reason? Becasue whilst personal effort and knowledge are involved in what we’ve done in our lives, so is good fortune and without a doubt so are other people.
When it comes to our journey into the next chapter of our lives it’s no different. We sometimes need frameworks to keep us accountable to what we promise ourselves.
Sometimes that requires other people, sometimes it doesn’t however I’d suggest the techniques with a decent bit of human interaction are probably the more powerful ones.
So, without further ado…
Here’s the reason you shouldn’t retire alone and the 5 tried and tested ways and 1 brand new way you should consider keeping your retirement journey accountable.
Self Reflect (with the help of a bloke called Gibbs)
It’s likely that in the upcoming chapter of your life you’re going to be trying loads of new things out.
However, instead of trying loads of new things there might be some value in thinking about how they might fit into the new life you want to build.
In 1099 Graham Gibbs created a model I believe might be useful to be aware of when you’re thinking about whether something you’re doing now might be the right fit for your new life.
Describe – What happened?
Feelings – How did it feel?
Evaluation – Was this experience positive or challenging?
Analysis – Why did things turn out how they did?
Conclusion – What did you learn and what might you do differently next time?
Action – What practical steps will you now take based on this reflection.
You can use this reflective model in so many ways, from trying a new sport or hobby, to trying to see whether work fits into the next chapter of your life, all the way through to what you spend time doing with friends and how you choose to get involved in the community.
The good news is that we can all self-reflect. However, it does mean that we might want to create some time in your day and get into the habit of self-reflection.
It also might help if we’ve got a tool to record our thoughts, which brings me onto my next suggestion.
Journalling
Journalling, the act of simply writing down your own thoughts, feelings, ideas and reflections either prompted by some questions or free flowing, turns all of the random ideas in your head into something with a bit more clarity.l
I find writing not only a cathartic experience but also an experience where I get to clarify my thoughts on a particular subject.
I’d recommend journalling or writing on a regular basis, using prompts and rereading past entries to not only see what progress you’ve made but also what you still might want to work on.
To help you with this process, we’ve built our own ‘What Happens Next’ journal which is only available both digitally or leather bound.
An accountability partner.
An accountability partner is a person – friend, family member, peer – with whom you share goals and check in regularly. Unlike a coach, this relationship is peer-to-peer, offering mutual encouragement and accountability.
Having someone on your side as a reminder, and as someone to hold you to account, as well a building empathy (and having fun) along the way might be really useful.
Here’s my tips for picking a decent accountability partner.
Pick someone you trust who wants the best for you.
Set a regular time to chat and where it’s going to be. Is it going to be a call, a walk, a coffee, or a digital check in?
Adjust what you need and feedback to each other on a regular basis.
However, you may want some personal help from a professional, here’s where my next suggestion fits in.
One to one coaching.
One to one blends emotional and practical support from a trained coach. professional coaches use frameworks to help you look at the stories you tell yourself about the world, ask challenging questions and allow you to think through your own thoughts on a particular subject.
A high quality coach can provide useful frameworks to think about either a particular challenge or the world, accountability and give feedback. However, my experience is that a great coach will hold up a mirror to your world to help you ask the right questions, reflect and make the right decisions for you.
Community groups.
Joining a community of like-minded people who are going through the same opportunities and challenges you’re facing might provide you with the right support.
Being part of these communities allow you to share experiences, learn from each other, support each other, share ideas and celebrate each others wins.
I’d certainly recommend you join the What Happens Next community when we launch it early in 2026. To be one of the first ones to find out when we launch the community feel free to join the waiting list.
AI Coach
A new addition to the list of support you might want to consider is how an AI coach might be worth considering as one of the ways you can get support.
We’ve developed an AI coach at What Happens Next and whilst it can’t provide the experience, insight and empathy of talking to an actual human, we’ve been really impressed at what it can do.
The good news is that an AI coach is available 24/7 and as the technology improves having an AI coach, in the same way as education will evolve with the use of AI in the next decade of so, might be something we all take for granted in a few years.
So, these are the ways I’d recommend you stay accountable when you’re on your own What Happens Next journey…
If you’re thinking about whether you’ve achieved enough financial independence to retire, you’ll benefit from our financial freedom in 3 easy steps video.
And
In this video, I speak about what we can learn about the Stoics to live our best ‘what happens next lives.’



