If the end of your professional life is on the horizon, it’s time to start thinking about what happens next says Helen Monument

So, all you Baby Boomers out there.  You’re in your late 50s or 60s and if you’ve not already come to the end of your working life, you’re thinking about it; or maybe even counting the months until you stop being an employee and become a retiree.

Just imagine your very first Monday morning when you realise that you don’t need to get up for the daily commute – ever again.  Are you thinking about the office, ‘How will they ever manage without me?’ or even worse ‘How am I going to manage without them?’ Perhaps you’re looking forward to your post-retirement dream holiday, the trip of a lifetime, but once the holiday feeling has worn off, how are you going to fill your days?

We are living longer, sixty is the new forty, and we’re all much more active than our parents were at retirement.

As an assistant, planning is second nature to me, never a day went by when I was not doing it. But many assistants I talk to tell me that they are excellent at planning for others, but hopeless at putting themselves first.  If the end of your professional life is on the horizon, now is the time to start thinking about your own plan for what happens next.  Where do you want to be, what do you want to do, and what do you need to get there?  I called my plan “From Retire to Re-Wire”.

It’s Your future

What has always been your dream? And what’s stopping you from fulfilling that dream when you decide – or someone else decides for you – that you’ve come to the end of your working career?  Whatever it is; learning the piano, writing a novel, teaching children to dance, getting a degree, landscape gardening or skydiving, now is the time to start making those plans.

Someone said, find a job you love, and you’ll never work a day in your whole life.  Well this is certainly true for retirement.  You finally have the time to spend on doing whatever it is that makes you happy, but as all good assistants know, failing to plan is planning to fail – so let’s get this project started.

Retire in style

The first step is to retire in style.  It’s going to be an emotional time, you are coming to the end of a phase in your life that has kept you in a certain routine for many years.  All that will change, and you may find it difficult to leave that life behind you, wondering how your organization will carry on without you in it. Well, believe me, it will carry on without you.  That’s why the last year of your working life should be all about letting go, handing over, finishing up, clearing out, closing down and saying goodbye.

You need to start at least a year before your leaving day.  It may sound like a long time, but remember as an assistant you are pivotal to the success of the organization and you’ve still got your day job to do, so you need to discuss and agree your leaving plan with your manager, to show how you will spend your last year at work and when and how you will hand over your responsibilities.  Chances are you already have a very busy schedule, but the 6-12 months before your leaving date is not the time to take on new projects or start new initiatives, but to focus on finishing up current work and preparing to handover, support your successor, then leave.

My manager and I agreed that the search for my successor would start six months before my last day at the office.  This gives plenty of time for posting the vacancy, interviews, selection and a working-in/handover period. I have worked hard to be a success at my job, so I want whoever takes over my role to be a success as well.

Work processes

Are your ‘how to’s’, checklists and manuals all up to date? Use the final year to make sure that your tasks and responsibilities are documented in your Work Process or Manual, ready to hand over to your successor.  Don’t forget to include your list of contacts.

Job description

Is it up to date? Chances are that in the past years you have been asked to take on extra tasks previously done by middle-management, or HR.  Make sure you include everything for which you are accountable.  It may appear that once it’s all down on paper, it’s too big a job for just one person, you have been a superpowered Assistant for so many years, right?  So, look for any development opportunities for someone else in your team to pick up one or two responsibilities. The final version should be an honest reflection of the job content, with clear deliverables and accountabilities, ready for the recruitment process.


Is your inbox full to bursting? Then you certainly need to spend time going through it and deleting all the emails you have been keeping, ‘just in case’. Send any personal information to your private email and empty your personal drives and desktop files.  Keep one folder with valuable information about ‘ongoing’ issues to pass on to your successor.


Create an overview of all the external websites you use for reference material or for services like buying supplies, ordering taxis – so that at the end of your last year, you can delete your accounts and make sure your successor applies for a new account.


Yes, we all hate it, and it’s always the last thing you want to do, but you owe it to your successor to leave things in good order, in an efficient (electronic) archive. Destroy anything with personal information – yours or anyone else’s (remember the GDPR regulations as well as following your own company policies on information management). Make sure your successor has access to all the online files that are needed.

Are you a team leader?

You’re not just leaving your job, you’re leaving your team.  They may be getting emotional or apprehensive about getting a new leader, so make sure you keep them informed of the recruiting process. Spend time with each of them in the month before you leave, thanking them individually for their contribution to the team.  Make sure their annual performance review information is complete and include it in your handover plan.

Select your successor

Nobody knows how to do your job better than you, right? Being on the interview panel makes perfect sense.  You will talk the same language as the candidates and you know what questions to ask when it comes to skills and experience.  However, be aware of unconscious bias.  People tend to choose people who are like them.  So, don’t fall into the trap of looking for a clone of yourself.  Organisations need new blood who see things differently, so don’t write off a candidate simply because they don’t ‘fit the model’.

Handover to your successor

OK, this is the hard part. You now have to handover your ‘baby’ to someone else to raise.  This is very challenging and can be quite emotional.  Your successor of course wants to put her/his stamp on the job, but you have a responsibility to your organization to ensure that there is continuity.  Be generous with your knowledge, prepare all the documentation you are leaving behind with work processes, checklists etc.  Make sure that all the systems access and software that you needed to do your job are transferred to the new person.  In my plan, I have given myself plenty of time to work together with her/him as I gradually hand over responsibility, but in some companies, you may only get a little as four weeks.  However long you have, get to know them and give them all the support they need, after all, you want to leave your manager and his/her team in a safe pair of hands.

Plan your exit interview

If this isn’t a policy in your company, make it your parting gift to your manager. It’s a wonderful way for you to say what you really think about how things could be done differently.  Tell your boss what you’ve loved about working for him/her, and how you think he/she could work even better with your successor. Ask for references before you go.

Clean out your desk

Don’t leave it till the last minute, so start a few weeks before, gradually taking down the photographs and the sticky notes with the inspiring quotes from your wall. If you do it a little at a time, it’s easier.  The same goes for your drawers and cupboards – how many pens do you need anyway? You certainly don’t want to leave your successor with the remains of your bag of muesli or mouldy biscuits.

Your farewell celebration

Discuss with your manager what kind of farewell event you would like. You may be lucky enough to have a budget to spend how you wish. Invite anyone who has helped and supported you in your career, you don’t have to invite everyone.  If it’s practical, plan the party the day before your last day, so it really is saying goodbye. Think about what you want to say in your farewell speech.  Remember it’s not the Oscars, so you won’t have time to thank every single person who has been a supportive colleague but mention those special people who have made a real difference in your career. Give yourself plenty of time to prepare, and practice, practice, practice – especially if saying goodbye makes you emotional.  You want to maintain your professionalism right up to the end, right? Make sure that your nearest and dearest are invited too.  They have been your support network during your working life and should be there to witness this milestone and be thanked for their silent contribution.

Your last day

If you plan has been successful, your successor will already be up and running in the role, so agree with your manager to come in for a few hours on your last day in the office. You should have finished all your work and done a complete handover by now, so it’s all about you saying your farewells.  Make it a day of celebration.  Buying cakes for the office on the last day is a tradition in some offices, but why not do something different, pizza at lunchtime, or savoury snacks later in the afternoon.  Take time to go around the office and say a personal farewell to those who are important to you.  You may want to leave a parting gift to those close colleagues.  Before your account is disabled, send your personal farewell messages to everyone, including your home contact details, if you would like them to keep in touch. You may have an off-boarding process already in place, so the day has come for you to hand back your laptop, accessories, access cards, parking pass, keys, manuals, etc.  Finally, your last hours in the office may be an emotional time for you, or you may go whistling out the door and never look back.  But it is the end of a stage in your life – and the beginning of the next, so carry on celebrating into the evening with family and friends.

How to Rewire

You may be one of the lucky ones whose company offers a pre-retirement course to those coming to the end of their working lives.  Even if you already have your rewire plan, it’s a terrific opportunity to hear valuable information about finances, pensions, lifestyle changes and health management. Partners are offered invited too, after all, your rewire plan will also affect the ways things happen at home.  My husband has been retired for a few years and has happily taken on the responsibility of running the household. However, we may have to rethink a division of labour if I am going to be spending more time at home. He certainly won’t want me following him around checking on his cleaning skills or editing his shopping list.

My rewire plan began three years before my target retirement date.

I started with a mind map.  In my career, I have used mind mapping many times and together with a SWOT analysis, it’s a fantastic way to get clarity and a vision about which way to go.

I wrote my name in a circle in the middle of a large flip-over sheet and started to brainstorm; my life, my career, my family, my strengths, my network, my home, my health, my finance, my hobbies, what makes me happy, what makes me sad, what gives me energy, what I love to do, what I hate to do, and I did not stop till the paper was full and I had run out of ideas and thoughts.  It was a very satisfying process and it made very clear to me that what I loved most of all – after my family – was my job!  So how could I use this knowledge to find a new pathway after I retire?

The answer was quite simple, I want to use the knowledge and experience that I have gained in my 30-year career in the management support profession to inspire assistants at all levels to be the best they can be.  It was quite scary to realise that I would be my own boss, but with much support from those around me and in our profession, Monumental Assistance was born.

And now for something completely different

It’s important to use your time wisely up to your retirement to learn additional skills or get training and experience so that you can rewire yourself to do something completely different.  One of the services I wanted to offer assistants was coaching, so I have used the time leading up to my retirement to take an international coaching and counselling diploma, to enhance the professional coaching skills I had learned in my career as a leader of teams of assistants.

As assistants, we already have an amazing number of skills including administration, language, communication and teamwork.  There are many (voluntary) organisations crying out for these kinds of competencies.  There are also many free online training courses that offer a variety of topics such as how to blog, developing your own website, creative writing, etc.

Even if retirement is not over the horizon for you, it’s never too early to start creating your rewire plan. Mind map yourself to find out what it is you really love – and what you are good at.  Ask yourself how you will fill the hours and maintain your path in a meaningful way, what will give you the educational, mental and physical stimulation that you need once you have reached retirement.

Many women of my generation have not had the chance to build up a solid pension, so retirement from one job may just mean a search for another (part-time) one to make ends meet. But you are now in control of the next step you take – your mind map will show you the things that excite you, so get creative about the next phase in your life. Now is the time to pay attention to your own plan, focus on staying healthy and look forward to whatever challenges you set yourself in the coming years.

Recommended Reading

There are many books available on how to deal with retirement, but these are some which address not the financial issues, but rather the philosophical ones, particularly for those whose work has been their entire life and are afraid that they won’t have a reason to get out of bed in the morning.

“Time for Wonderlust – Planning your retirement renaissance” by Forrest J. Wright.

“What will I do all day?” – Wisdom to get you over retirement and on with living. By Patrice Jenkins.

Helen Monument inspires and encourages Assistants to be the best they can be by sharing 40 years of experience as a management support professional. Her career has taken her from Secretary to Office Manager and Business Support Team Leader, so she ... (Read More)

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