A special thank you to Fritz Golbert for permission to share his steps in planning for Retirement.   
1. Maintain A Checklist
18 months before retirement, I started a checklist with everything I had to address before retirement.  You can start with the 20 items from this post, then add to it as specific tasks come to mind.  It was a lifesaver for me and became the roadmap that led my tasks as I made my final preparations for retirement.  I listed each month between “now” and “retirement”, then populated various tasks into each month and referred to the list each month to ensure I was on track.   It doesn’t have to be fancy. Here’s an actual screenshot from March, with X’s to confirm the tasks were compete:

2. Talk To Your Boss, and Talk To HR
As I laid out my 12-month checklist, I planned several meetings with my boss and the Human Resources department.  My first meeting was with my boss at the one year mark, as I’d decided I was going to be very transparent about my plans and allow time for a smooth succession.  It was a risk to approach “the boss” so early, but I felt it was important to provide my employer with as much time as possible to plan for my departure.  I have no regrets about my approach, and my employer appreciated my support in the transition planning.

I also had numerous meetings with HR, starting at higher level discussions and branching down into some very specific meetings with “specialists” (COBRA insurance, timing to ensure I maximized my bonus payout, transition deadlines, etc.).  I also clarified the terms of my non-compete agreement, given that I had been offered a Board Of Director role at a company in our industry when they learned of my retirement  (note, I did NOT accept the offer until I had clarified the non-compete with our Senior Management team.  Do it right or don’t do it at all.)
My final meeting with HR was actually my last work-related activity, as I turned in my laptop, company credit card, building security pass, parking permit, etc.  It was a positive experience, enhanced by my transparent approach to my retirement plans.

3. Talk To Your Spouse
It may seem obvious, but retirement doesn’t just affect the person leaving the workforce.  In our case, my wife had been a stay-at-home Mom since our daughter was born, and the adjustment of having me home all of the time was going to be a big change in the way she’d lived her life for 20+ years.  If you’re married, make sure you’re planning retirement together.  Incorporate things that are important to both of you for your retirement dreams, and keep an ongoing discussion about the big changes you’re both going through.

While you’re busy at work in the final year, it’s easy to forget that you won’t be spending time with your co-workers after you retire.  Recognize that your spouse is more important than your work, and treat him/her accordingly.  You’re going to be spending a lot of time together in retirement, it’s important to get it started on the right foot.  Unfortunately, “gray divorce” is a real thing, and I suspect many of these unhappy endings could have been avoided if spouses took the time to talk with each other about their individual desires for retirement.
4. Migrate Your “Personal” Stuff from Work
For years, I used Microsoft for everything.  I had tons of personal files on my work computer (it was my only “real” computer for years, though I did have a personal Chromebook I used for writing my blog).  I didn’t want to pay for Microsoft in retirement, and I was happy with the Google toolbox (Google Drive, Docs, Sheets, etc).  I spent ~12 months migrating my “personal” files from Microsoft on my laptop to my personal Google Drive, converting them from Microsoft to Google formats in the process.  Every time I opened a “personal” spreadsheet or file on my laptop, I either migrated/converted it on the spot, or added it to my checklist of items I needed to migrate.  It took some time, but it was manageable.  
5. Migrate To A Password Manager
I started keeping track of usernames and passwords YEARS before password managers were invented, and I (like many of you, I suspect) simply kept using the system I had developed to keep track of them all.  For me, I “hid” them in my work files, which were kept on a secure server behind my companies firewall.  It worked fine for years, but I knew I’d lose access to them after I retired.  It was time to migrate to a password manager.
For a year, every time I logged into a site which required me to “look up” my password, I made sure it was captured in my password manager.  For the record, I chose LastPass and have been happy with it, though I’m sure any of the top shelf password managers would suffice.  LastPass automatically captures a new site and saves it, so most of my sites were captured simply by having it in place “long enough” to ensure I’d signed into most of my important accounts.  In the final few months of work, I went through all other accounts still in my secret “work file” hiding place, and made sure they were captured in LastPass before I walked out the door for the last time in June.
LastPass also has a place to keep “Secure Notes” which I used to save confidential information I’d previously kept “hidden” behind my companies firewall (e.g., my “loyalty card numbers”, and instructions for how to unfreeze my “frozen credit files” should I ever need to apply for credit).
6. Update Your Profile Data
As you work through the various sites via your Password Manager, take a few minutes to ensure your personal profile data is updated on the various sites.  If you’ve listed your work phone/email, make sure you update it to reflect your post-retirement contact information.  If you’ve used your work email to sign up for newsletters, make sure you migrate them to your personal email.
I made a point of watching my work email throughout my final year and taking a few minutes to update any site which sent me emails to my work address.  It’s surprising how many different places you’ve used your work email, and it’s impossible to remember them all.
7. Design & Implement Your Retirement Paycheck
As I wrote in How To Build A Retirement Paycheck, I designed a system where I would keep ~3 years of cash in “Bucket 1”.   I designed a system where ~1 year of these funds would be kept in a separate account at another financial institution, from which I would set up automated transfers 2X/month into our personal checking account (my “retirement paycheck”).  No other “spending money” would be transferred in retirement (e.g,. I intentionally kept my Vanguard Money Market account “off limits”, for use only in managing my investment portfolio and not funding my retirement expenses). By simply looking at my Jan 1 vs. Dec 31 balance in the CapitalOne account, I could easily quantify my annual retirement expenses which had been funded from my portfolio.
As I worked through the final 12 months, I established and funded the CapitalOne account, and did my final detailed analysis on funding requirements.  For some reason, I was only able to transfer $10k at a time to CapitalOne, so I was happy that I had built sufficient time into my plan to transfer money over several months.
8. Establish And Migrate To A Personal Calendar
I had always used my “work” calendar to track all of life’s activities.  This calendar “lived” on the Microsoft exchange on our company servers and was automatically synced to my work cell phone. I would no longer have access to either of these tools after my retirement and had to develop a personal calendar.
I decided on Google Calendar and began putting all personal items on Google calendar to get familiar with it.  I also entered anything which was scheduled for after my retirement date on the Google calendar, and continue to use it to this day.  No calendar entries were lost in my transition into retirement, but it took a plan and implementation well before my retirement date to ensure nothing was lost.
9. Copy Your Work Address Book
Similar to my calendar, I’ve always kept my address book on my work computer.  Since I first had a PalmPilot way back in 1998, I’ve been storing contact information electronically.  Most recently, it was all kept in Microsoft, again on our company server.

Fortunately, I had a friendly IT Help Desk contact who was sympathetic to my cause and invested significant effort on his part to migrate all of my information from my work server to Google Contacts. This was one of the items I worried about as I thought about my retirement, but I was fortunate to find a way to capture over 20 years of contact information and continue to maintain those addresses post-retirement.

Ironically, with Social Media these days, the majority of my post-retirement contact with folks I’ve known over the years has been through the Instant Messaging platform on LinkedIn, Facebook, Twitter, etc.  If you don’t yet have a presence on LinkedIn, I’d suggest you set it up before you retire, it’s a great way to keep in touch with previous colleagues once you’ve retired.
10. Develop a Plan For Health Insurance
As outlined in Health Insurance:  Unsolved, I made the decision after several meetings with HR to extend my company insurance for 18 months under the COBRA plan.  This is not a decision you want to make in your final month of work.  Build it into your monthly checklist (Item #1 above) in various stages.  For example, 12 months out I started doing some preliminary research on COBRA and other options.  As I got closer to my retirement date, I started fine tuning my decision.  I also learned (in another HR meeting) that it’s best, if possible, to avoid scheduling any doctors appointments for ~a month after you retire to ensure the transition to COBRA is implemented with the minimal chance of disruption.
11. Decide On Your Pension Details
As mentioned in Our Retirement Investment Drawdown Strategy, I realize I’m a fortunate dinosaur, and having a pension is rare these days.  My company discontinued pensions for new hires more than 10 years ago, but elected to “grandfather in” existing employees.  Whew, close call.  With 33 years at one employer, the pension is a significant element in our retirement plan, but it has to be managed.  As mentioned in the Drawdown post, I elected to defer the start of my pension.  The process of understanding my options and implications took several months and is something you want to add to your checklist at least 6 months before your retirement date.
For those without pensions, you should add an item to your checklist to ensure you understand any retiree benefits you do have available to you, and optimize them for your situation.
12. Dream More, Work Less
“Work Less” isn’t really what I mean by this point.  Rather, it’s to realize that when you retire your work activity will cease.  Rather than approach retirement as a “Cliff” (see Unprepared For Retirement), be intentional with your mind in your final year of retirement.  I never “worked less” while I was actually at work, but mentally I was changing gears.
Spend time dreaming about what you want your retirement life to be, and spend less time thinking about work-related activity.  Start building a Bucket List of things you want to accomplish in retirement, including things beyond “travel”.  Research has shown that this is one of the most important steps you can take to ensure a smooth transition to retirement, so make sure it’s on your checklist as you work through your final year.  For further details on this topic, read my post “Will Retirement Be Depressing“.
13. Start Some Hobbies
On a similar note, find some time in your final year of work to experiment with a few hobbies that interest you.  Don’t wait until retirement to decide what you’re going to do, but rather spend the final year of work exploring some potential areas so you’ll “hit retirement running”.  Research groups in your area that interest you.  Join a local gym.  Get more active at your church.  Start being intentional in expanding your circle of friends outside of work.
Dream more, and start experimenting with the things you’re dreaming about.
14. Buy Your Retirement Toys
As you think about retirement, think about the “toys” you’ll need to live the retirement you’re dreaming of.  In our case, it was a 5th wheel and a truck to pull it with.  I’ve heard from others who have gone before me that it’s difficult to make these “larger acquisitions” after you retire and that paycheck stops, so build them into your plan for the year prior to retirement.
We built a spreadsheet to help us achieve our “Starting Cash Level” for Day 1 of retirement.  In the year leading up to retirement, we listed all of the projected inflows (e.g., Bonus) and outflows (e.g., RV) to keep ourselves on track to achieve the Day 1 cash level without overspending.
We hit our targeted Day 1 level, and we secured our retirement toys without anxiety.  Now that we’re retired, we have peace of mind that we’ve positioned our retirement to be the best that it can be, without overspending on the “toys” we’ll be using in retirement.
15. Address Your Retirement Housing
Don’t wait until retirement to figure out your post-retirement housing situation.  In our case, we intentionally made The Move From Good To Great while we were still working.  It worked well for us and allowed us to enter retirement all settled into our retirement cabin in the Appalachian Mountains.
A friend of mine retired a month before me and decided to move from Atlanta to Spokane for their retirement.  Since his job was in Atlanta, they decided to wait until shortly before their retirement to put their Atlanta home on the market and made the transition to Spokane via RV shortly after their retirement.
Others decide to retire in place and should consider which upgrades/modifications they’d like to make to their home for retirement.  Planning those upgrades during your last year of work
makes sense, as spending for the upgrades is less stressful when there’s still a paycheck flowing.
Do whatever works for you, but make sure you think about your retirement housing options during your final year of work.
16. Replace Your Hardware
Prior to retirement, I never owned a personal cell phone!  Since my employer allowed us to use our company phones for personal use, it never made sense to spend money on something I was able to use for free.  As I approached retirement, I worked with our IT team to understand how I could migrate my cell phone number from my work phone to a personal phone, allowing me to keep the number I’d had for years.  We were able to work it out, and it allowed all of the folks who had my “old” cell number to keep in touch with me after I retired.
Several years ago I decided to migrate to a Chromebook for my blog work when my personal laptop computer wore out.  For retirement, since I’d no longer have access to my work laptop, I decided to buy a “real” laptop for use with video and photography editing, as well as podcast interviews.
17. Make A Retirement Budget, and Live On It
By the one year mark, you should have a pretty good estimate of your annual retirement expenses. Aside from the “one-off” expenses outlined above, attempt to live your day-to-day life within your projected retirement budget.  A year before my retirement date, for example, I stopped buying clothes.  While there are obvious expenses you’ll have while working (commuting, meals), make an effort to replicate your retirement lifestyle and expenses.  If you find yourself spending more than you’ve planned for retirement, it’s good to know while there’s still time to make adjustments.
18. Put A Countdown App On Your Phone
I enjoyed watching my countdown app whittle away throughout my last year of work.  It was a helpful reminder of the reality that retirement was coming, and helped me focus on the important things.  Find a way to distract yourself from the busy-ness of work, and keep your primary effort on ensuring the best possible transition into retirement.
19. Take Time To Say Goodbye
Work life is hectic, and it will remain so until the end.  I was intentional in dedicating my last month of work to saying goodbye, and I’m pleased with the way my career ended.  Plan some business trips to say goodbye to the folks who have meant the most to you through your career, and start letting your successor run the day-to-day business.  After you retire, you’ll no longer have an opportunity to say goodbye the “right” way, so prioritize it while you’re still working.
Carve out some time in your final weeks to write a few personal notes.  Make some phone calls to say goodbye to folks you won’t be able to see.  Plan more lunches out with “friends” over your final months.  Let folks know you appreciate them and have enjoyed working with them. We all think we’ll keep in touch after retirement, but no one really does.  Sad, that.  Realize it’s likely going to happen to you, and take time to say goodbye before it’s too late.
20. Enjoy The Ride
Perhaps most importantly, take time to enjoy the final year of your working career.  You’ve come a long way since you started your career, and you’ve put yourself in a position to be able to retire.  Congratulations!  Enjoy The Ride, and be introspective as you go through many “work-related” things for the final time.
I enjoyed sitting through our final budgeting meetings. 
I smiled as we talked about the need to prepare the dreaded annual strategic plan.  I joked with my boss as we did my final year’s performance appraisal.  Have some fun with your final year at work, and don’t stress about it.  Before you know it, it’s all going to be behind you and you’ll be living an entirely new life.  This is your last year of work. 
Smile more, and worry less.
The transition into retirement is a major life change.  Having a detailed plan to manage that transition was helpful in our retirement, and I recommend you consider developing your own steps to take in the year before retirement.  By using these 20 items as the baseline for your personal checklist, you’ll have less stress through the journey and be able to enjoy your final year of work.
You’ve worked hard to get to this point.  It’s time to reap the rewards.
Enjoy your final year.
You’re going to love retirement.
If you are interested in learning more follow Fritz at www.theretirementmanifesto.com.