So, for as long as you can remember (through both work and education) you’ve had a structure to your week which you wrapped the rest of your life around. Now comes retirement, the big moment when you can do what you want, when you want, but there is no longer a structure to support you. It’s like trying to navigate to an unknown destination without a map or directions.

Retirement is exciting, but without some structure, it can feel aimless so let’s look at the options:

1. FREESTYLE: Hey structure is what you’ve been longing to get away from, so play it by ear and just let life happen!
2. CREATE AN ALTERNATIVE STRUCTURE: Alternatively, create your own version of the ‘working week’ based around what you WANT to do rather than what you have to do.

FREESTYLE v ALTERATIVE STRUCTURE

Which way should you go?

Ultimately it’s down to you – your personality and priorities – but this in what I’ve found:

1. freestyle

Some people embrace complete freedom once work ends.

A number of friends have taken this route and, from what I’ve seen, it can lead to slower starts, drifting through the day and becoming surprisingly good at “killing time”. A quick trip to the shops, a coffee stop and choosing lunch can easily become the day’s main events.

The advantages

• Complete flexibility
• Minimal stress
• Freedom to be spontaneous
• No rigid timetable

The downsides

• Leisure time can be wasted
• Days may start to feel repetitive
• Lack of purpose or momentum
• Possible negative impact on mental wellbeing

2. CREATE AN ALTERNATIVE STRUCTURE

This approach replaces work-related “mileposts” — meetings, deadlines and appointments — with leisure activities, hobbies and personal goals.

The result is a familiar weekly structure, but with one major difference: you can ignore it whenever you choose.

The advantages

• Gives you a reason to get up in the morning
• Helps you make better use of your free time
• Keeps evenings and weekends free for friends and family
• Creates routine without the pressure of work

The downsides

• It’s possible to over-schedule yourself
• You can accidentally recreate work-related stress
• Too much structure may reduce the sense of freedom you worked hard to achieve

Ultimately, it’s about balance.

Which approach works best for you?

Have you chosen complete freedom, a more structured routine, or something in between? Let me know in the comments.

LEISURE ‘MILESTONES’

If you choose the structured approach, what milestones can you use?

Your leisure milestones can be whatever you want them to be.

They could be something based around your main interests, like meeting up with friends, sport or gym sessions (golf, walking or maybe even watching sport) or voluntary work. Slot these into the diary as your ‘milestones’ each week and then add in chores, hobbies etc around them.

PERSONAL DISCLOSURE

It probably won’t come as too much of a shock when I tell you that I’ve chosen the structured approach.

I originally planned to use gym sessions as my main ‘milestones’ but found that my self-imposed challenges (365 days of photography, LinkedIn, this blog etc.) automatically became my milestones…but it doesn’t matter since I still have a framework to use.

CONCLUSION

Choosing the freestyle approach can be tempting but may leave you directionless and unfulfilled. On the other hand, creating a leisure-based structure offers the chance to make the most of your free time and to achieve your new goals but you can take this too far.

MY UPDATES & TIPS

UNEXPECTED ITEMS/ THINGS THAT I HADN’T ANTICIPATED

Here are some of the things that I hadn’t anticipated in my retirement journey:

1. Challenges Are Time Consuming – I underestimated how much time my 2025 challenges would take up. So don’t be surprised if you find that you can’t fit as much into your day as anticipated.
2. Isolation Isn’t An Issue – Experience shows that many people can experience loneliness in retirement. I was therefore concerned that I’d start trying to fill the ‘social void’ by asking my wife about her workday which, if taken too far, can just be living your life through someone else. However, I’ve found that I gain all of the external social interaction I need through all of my projects and activities.
3. Working Part Time, On A Freelance Basis, Is Harder Than You Think – On my original blog, I said that I still wanted to spend some of my time working on projects or in short term roles. Achieving this goal is much harder than I anticipated and the opportunities that I’ve found have come from the least likely sources.

In addition, I hadn’t considered some making decisions that I needed to make such as:

1. A fitting description for the service that I’m looking to offer,
2. A business name,
3. Logos, signature blocks and other supporting materials &
4. How to connect with potential customers

TIPS & SUGGESTIONS

Here are some further tips that I’d like to share (based upon my experiences to date):

• Don’t Over Plan or Over Commit – There is a danger that, in your search for a new life, you’ll commit to too many things.  I’d suggest that you start slowly and build up.
• The ‘Gofor Promise’ `Needs Constant Care & Attention – You really do have to revisit this subject (see explanation of this promise below) on a periodic basis to maintain its existence.
• Keep a diary – One thing that friends and family will keep asking you is ‘what have you been up to this week’ and you may well find it hard to answer. Keeping a diary is an easy way to deal with this and helps you to spot activities that you may want to explore in more detail.

* The ‘Gofor Promise’ is a commitment,  from my family, that I have the right to spend my ‘spare time’ as I see fit rather than be the person who is now there to pick up all of the odd jobs, housework etc.

‘EARLY RETIREMENT’ – HOW’S IT GOING SO FAR?

Let’s see….

• BLOG – This is my second publication and I’m learning as I go along. I have therefore now added social media sharing buttons, a ‘Subscribe’ button plus an extra page describing my 365 Project (see below).
• 365 DAYS OF PHOTOS – If you are interested, please follow the link below outlining the project itself and the resulting images to date. 365 DAYS OF PHOTOS
• LINKEDIN – I’m continuing to publish 1 post per week. If you’ d like to view my articles on business, management and my freelance business adventures please use the following link: LINKEDIN FOR PHIL
• TRAVEL – We’re just come back from India (more about that in a future blog) and I managed to combine some work with a few days travelling in Cornwall.
• Freelance Work Projects – I have 3 sets of work projects on the go:
• Automotive Finance Projects: I’m working on a different approach to the contract hire & leasing market (longer term project),
• Coaching/Training: I’m hoping to announce starting a new role as a training associate in the near future,
• Sales & Account Management: I’ve enjoyed doing a number of Trade shows and, as a result, have just been asked to perform a short-term National Account Manager role (in a product area way outside of my finance background).

This freelance work project is therefore going well BUT I am mindful of picking and choosing projects that fit in with my leisure aspirations. (I will cover this topic in greater depth in a future blog.)

Questions?

Here are the questions and answers generated by last month’s blog:

Question	Answer
How does your idea of a starting position of saying ‘Yes’ to everything fit with the ‘Gofer Promise’?	I do now start from a position of saying ‘Yes’ (in order to be more open to new experiences). However, I then move to a position of ‘No thank you’ if I see the offer as just a way to offload a chore that I really don’t want to do. It’s a fine line but I’ll give some examples in a future blog.

If you have any questions on this, or previous blog, please drop them into the comments below and I’ll address them in the next edition.

WHAT CAN YOU EXPECT TO SEE IN FUTURE BLOGS?

• Next month I’ll be taking a ‘Travel Detour’ to look at travelling in retirement (including thoughts on long v short haul adventures, planning for the trip and some tips). It also gives me a chance to share of some of the photos from our recent trip to Northern India!!

I hope that you’ve found this blog interesting, and I look forward to hearing your thoughts on ‘retirement’.

1. How do arrange your week?
2. What do you do with your time?

SHARING THE BLOG & COMMENTS

• SHARING: Please share the link to this blog, with anyone that you think may be interested (social media sharing buttons are provided below) and subscribe.

• COMMENTS: Likewise, if you have any further comments then just share them below.

Until next month..

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Every chapter of the Rookie Retiree Journal explores a different side of life after full-time work — from personal stories to health, purpose and travel.

Want to explore a little further?

👉 New here? Start with the WELCOME PAGE

👉 Looking for something else? View the full CONTENTS PAGE

👉 Read related items on this topic here:

• THE START
• FINDING FULFILLMENT AFTER 9-5
• DECLUTTERING & DOWNSIZING
• THINGS THAT NO ONE EVER TELLS YOU ABOUT RETIREMENT

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Regards

Phil Marsh is the creator of Rookie Retiree, exploring life after work — the choices, challenges and possibilities that come with the luxury of choice.

https://rookieretiree.com/2025/02/23/rookie-retirement-journal