Working together to keep the complicated simple

Freelancer/contractor plan for retirement

This article focuses on the practical and emotional side of approaching retirement, rather than the financial/pension side.

It’s a guest post from Neil Williams. A qualified coach, as well as the independent trustee of the Maslins Employee Ownership Trust.

Take it away Neil!

Elderly couple on a seaside bench

I was out with a freelancer at the weekend, who raised the issue of how he’d retire. Our conversation demonstrated mentally he isn’t ready for retirement yet, but does need a plan.

Initially, I said why not cut down to 4 days a week. “But what about my customers and their expectations of me”.

When pressed further “But, what about my values from my Dad re hard work, plus I’ve been self-employed for decades, how can I make that change?”

My friend isn’t ready for 4 days a week, let alone retirement!

How will you be ready for retirement?

Most of us have stages when we feel “stuck”. It’s normal to go through phases and have feelings like these. For some, facing retirement, planning your finances and future can be daunting.

The great news is there is a lot of information out there on planning your retirement including:

Steps to a successful retirement

Are you going to be a:


Gradually reducing the hours you work as retirement approaches. This often involves going to a 4-day week, then 3-days over a spell of years. It gives you time to try out new hobbies or other work you might want to do. As a freelancer how would you manage this?

Cliff edger

Cliff edge

Working full-time right up to retirement. This can be scary. When my wife did this, she ensured she finished projects she was working on, carried out a structured handover and left at the end of year so she could gain her own closure at an enjoyable time of year and achieve the objectives she had set herself. As a self-employed person, unless you are selling the business, this option may be difficult to manage.


Gradually increasing the amount of holiday you take. I know somebody who is doing this and from this summer, will only be working 30 days until the end of the year. It is OK for some! How can you adjust your customers thinking and expectations?


Finishing one career and starting another. This is what I have done but over a measured period of time. My previous contacts had to get used to me being a listening coach rather than a driven sales manager.


No commitment to retire. I have met many business owners who have done this and are as “sharp as a tack” in their 80’s. This is the danger for the self employed unless you have a plan. Probably the biggest issue is to be ready for it emotionally. Instead of saying, what will my customers say, or assume you know what they will say, how can you change their expectations, or reduce the number of customers you look after?

A combination of the above?

Some questions to ponder

  • What do you enjoy doing?
  • What other pressures or demands may you have?
  • What does your partner enjoy doing? What will you enjoy doing together? How will you create space for each other?
  • How will you go from a full-time working life to retirement or pre-retirement (working fewer hours but still earning money)?
  • How will you adapt from saving for retirement to spending your pension/savings. This is a major mental shift. 40 years financing a retirement, now you can start spending it!
  • What else concerns you about retirement – loss of ego, purpose, fulfilment, friendships, challenges or just doing something totally different without a work routine?

Coaching for retirement

For the self-employed, retirement is more complicated and often they’ll benefit from a coach to help them change. Otherwise they’ll remain an open ender and never attain proper retirement.

It’s even more important to have a plan, after emotionally adapting to the thought of giving up this role you’ve strived for and built up a great business. Where and when will you start planning for you retirement?

If the above struck a chord, Neil Williams offers retirement coaching. This starts from just £300 for two structured Zoom sessions with time to ponder in between…plus our tax bods are happy it’s businessy enough to qualify as an expense for corporation tax purposes!

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