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Transitioning into Retirement – Part 3
February 23, 2022

Transitioning to Retirement

The final year before retirement!

Your emotions may be a mix of excitement, anticipation, anxiety, and stress or maybe even fear. You may be thinking, “What am I going to do when I walk out this door?” Hopefully you have read our previous two blog posts on Part One (5-10 years out) and Part Two (1-5 years out) where we gave key strategies and action items to help you prepare prior to this year.

In this post, we are going to give you some steps that you can take now and over the course of the next 12 months to help ease your stress and build excitement about your retirement. We want you to be fully prepared for some of the key risks and feelings that are coming your way. We talk about these feelings a lot in our Retirement Transformed Facebook Community.

The feeling of being irrelevant.

You may feel this as soon as you announce a retirement date. You may feel irrelevant knowing that you will be replaced. This feeling happened to me. I announced my stepping down as the office leader two years before I left, and the next Monday weekly leadership team meeting was held without me. I wasn’t even invited. Irrelevance is a real feeling, and it often leads to a feeling of a loss of identity. How do you answer when people ask what you do, who you work for, what’s your email address? For some people, their entire identities are wrapped around their company and career.

Time affluence, or an abundance of time.

It’s not always a risk, however it can be. You are about to get 40+ hours a week of free time. And sometimes it comes a little early if you are phasing into part-time retirement and then full retirement. This happened to me, I was semi-retired and started coming in late and going home early. I started watching TV and got addicted to watching Ellen, and then I think red wine. Yes, afternoon red wine! I was going down a bad path using this time affluence poorly.

Loss of community.

This can be rough for so many people. Your work often becomes your family or friends and how do you replace those relationships when you move into retirement?

We’ve created a three-part checklist of the things you need to think about in preparation of the next few months. Part one is career/work-related, part two is a personal checklist, and part three is really focused on your first week at home.



Taking care of things on the career end. The first thing you need to do is to schedule meeting with your Human Resources representative to discuss your pension (if you are lucky enough to have one), 401(k) and health insurance. Some companies offer outboarding support, if yours offers it, you should probably use it. During the last 12 months, you will start getting a lot of structure in place. The next thing in your career transition will be having a talk with your colleagues. You need to talk about your transition, your replacement and how you can help make that seamless. You will want to talk with your leadership team individually and as a group to ensure they are set up for success after you are gone. Then, of course, there is communicating with your teammates and all of your clients. There are a lot of people that you need to have a way to transition your relationships with. Will they still be a part of your life in post retirement times and how will you be in communication with them after you leave.- I remember that on my last day of work, I wrote this great email letting everyone know how grateful I was for my time at the company and wished everyone well. At the conclusion of the email was my personal email address in case anyone wants to contact me. I waited all week long and finally one person sent an email. It’s not a reflection of who I am, it’s just that when you’re gone, that it, you’re gone. But the other thing around identity and email is there was a bit of a blend for me between my career and my personal life because I owned the company. My company was a major part of my identity, my personal email not so much. That changed.

Here is another thing to think about. As I started to get near the end of my time at work, I realized that my browser at work had all my bookmarks for favorite site and my login email was my work email. I had to make a list of everything so that my home computer could match and I would have access to my favorite sites. My passwords were all saved somewhere as well. It will be important for you to get all of that information into your personal email before you leave on your last day. Often, once you have left on that final day, it can be very difficult get back into your work computer to get access to anything.-

Depending upon what you are going to do after you leave, you may want access to some of your other digital records. For instance, if you are planning to work in a second career position, you may wish to have some presentations or letters saved to a thumb drive for future use. This of course also depends upon you company’s policies around the use of digital files. You also may want to requests letters of recommendation in advance in case you will need them for a future consulting job if that is a potential direction for you.

The final good bye. You may be thinking “I don’t want a party, I just want to get up and go”. This can be tricky…sometimes the retirement party is as much for the people you are leaving behind to help them provide closure as it is for you. Again, think about it in terms of who will you want to keep in touch with, who will you be closing a chapter with and what is the best way to either close the loop or keep the connection going.


Your Personal Checklist. By now, you should have a financial planner in place, an independent advisor who can help you make some important financial decisions as to how to help your money last throughout your lifetime. We are always so surprised at how many of the clients that we meet with who are married with kids and retire have no wills, nothing. This is a great time to get that done. When you leave your career, you want to leave organized and ready for your next chapter. You will want to notify your family and close friends about your retirement plans and your exact date of departure. They too, may need to update their forms of communication with you, for instance, your email address or mobile phone number if this changes. It important to also get in alignment with your spouse. Make sure you know what their plans are, how you fit in, and how they fit into yours. Be aware of how your retirement is going to affect the people around you.-This is really important.
There are so many couples that have wonderful relationships. They both work, they both have work friends and they are busy all day long. Some of these couples only meet for dinner or they’re together on weekends. Then, all of a sudden, retirement comes and they are thrown in 24/7 togetherness and they don’t know what to do. They don’t know how to interact eight additional hours a day. Or maybe one of you is just now retiring and the other has been retired for years. We tackle this in our online course and have many tools and strategies to help.

Make sure you share your retirement plans broadly, perhaps create a group of colleagues and friends that may also have retired ahead of you. In addition to our resources, this close knit group of your contacts can help support you through this transition.

Consider a gap year. We have a client who was financially set, but might consider future opportunities. He made a deal with his wife that no to any opportunities that came along for a whole year. The idea was to give them a chance to hang out and get a little more fluid, find a rhythm and it worked really well. Another option, sign up to volunteer. Create some space in your schedule to keep you active and giving back in a positive way. Last on our checklist, HAVE FUN!


Now is the time to start thinking about routines that will serve you well during that first week at home. Think of things that bring you joy and energy, proactively participating in the day. You should of course enjoy some downtime and definitely the freedom you’ve earned but don’t squander all of the time. There is this great feeling of relief of not having to go to work, have meetings, etc. But the thing is all of a sudden now you’re not really sure what to do. If you did the planning we mentioned in the first blogs, you should really have a plan for the five pillars of physical wellness, mental wellness, relationships, spouse/partner and wisdom sharing/community.

Consider adding some placeholders in your calendar. Look at what the beginning of a routine could look like for you. Weekly coffee with a friend on a Monday, some sort of activity physical activity on Tuesday and Thursday, and perhaps some self-care on Fridays. Find a way to incorporate a little bit of routine, especially that first week so it doesn’t go by in a blur. Before you know it, three years could go by and you haven’t figured it out yet. Start with some structure for ideal success.

We started a morning routine that has evolved over the last few years, but it is in fine shape now. It didn’t work at first and needed the flexibility to make changes, however now we have a system down that brings us both great joy.

This last year is really going to fly by. We want you to do all you can to be ready for the last day. If you follow our advice in these three posts for transitioning into retirement, you will have clarity, purpose, momentum and direction to land softly into this phase of your life.