9 Key Steps When You Want To Let Your Work Know You Want to Retire

oak harvest financial group Oak Harvest Financial Group

You’ve worked for yearsdecades – toward a time when you could step back and change direction in life. Whether that be relaxing and enjoying life at a different pace, spending large chunks of time engaging in volunteer work, consulting (on your terms) or even starting a new career.

All that planning and anticipation, but you can’t afford to overlook a very important consideration. How do you actually go about retiring?

There are many issues and considerations to be aware of in the period before you plan to retire, ranging from ensuring you and your spouse are on the same page, completing a review of benefits and examining your budget, gathering all retirement-related documentation, speaking with your advisors (financial advisor, retirement planner or accountant), preparing when to inform your company, how to let your co-workers know, and a ton more.

In this article, we are going to cover nine key steps to help you start the process of retiring and getting on to engaging in the next stage of life.

The Gold Watch

For many people, the idea of retiring is that traditionally portrayed in movies, shows, and the media. You go in and have a quick party, collect your gold watch and then walk out with a box full of personal mementos from your office and head for the car.

And then you step into the next stage of your life – retirement!

Well, there are elements in that narrative that are true, but the fact is there is a lot more that goes into actually retiring from work and transitioning into the next stage of life. Some very critical issues and decisions could impact your life going forward. And that can help you feel good and proud about how you capped your professional career.

First Things First

Free vector team starting project

Before getting into the nitty gritty about walking in and providing notice to your boss, employer, and fellow employees, just as with every other aspect of life, there are some things you need to do first.

C’mon, did you think it would be that simple?

Joking aside, this is a huge event in your life and that of many others. You need to speak with your spouse or significant other if you have one, especially if you are both retiring. There’s also your employer, supervisors, and fellow employees.

Yes, they will go on, but they came to count on you. And hopefully value you. And some within the organization will truly miss you. Consider letting them have the opportunity to say thanks, well done, and goodbye.

Before you get to the goodbyes and well wishes, there are some steps that you should undertake that will inform you as to whether now it the right time. These steps will give you confidence in your decision, or tell you there is more to be done before moving forward into retirement.

  • The Talk

If you have a spouse, a partner or family you are close with, before doing anything else, have a conversation with them about what you are considering. Best to share thoughts and plans with those you care about.

This can involve issues like moving somewhere warm to retire, taking steps to improve your heath, spending more time with family, and more. As well as whether they think it makes sense to step away sooner or later.

In the case of a spouse or partner, you need to be sure you’re both on the same page. Are you both ready financially, psychologically and practically. If one won’t be retiring right away, or even for some time, issues can arise that should be talked about in advance to ensure both parties agree.

Coming home from working a long day to see the retired person lounging can sometimes illicit resentment. Talk about things in advance so they don’t become issues later. Most importantly, ensure you are on the same page in terms of what your retirement needs, goals and dreams are.

  • Is This THE Time?

Once you’ve had the talk, then you must assess the lay of the land. There is an old maxim, “There’s a season, a time for every activity…” That is most certainly true in many areas of life, but especially so when it comes to retiring.

12 months ago you might have been sure you and/or you spouse would be retiring within a year. You drew a circle on the calendar for March 30th and made a promise you’d be sticking to that date hell or high water.

But then life happens. An economic downturn and you realize you might need to be cautious and put off the decision. Or an injury or illness, an issue with one of your kids.

There are countless issues and scenarios that can arise that may well affect your decision as to timing your retirement.

While such a delay may be disappointing, it’s just like every other part of life – you learn to accept and adapt. In this case, the timing just isn’t correct, so you adapt your plans and understand the time is not now, but the day will come soon enough.

  • Personal Finances

You’ve gone through the previous two steps and have passed go.

Now it’s time to do the nuts-and-bolts work. It’s time to review your personal finances, focusing on the present and the future.

To do so you’ll want to create a family balance sheet if you haven’t already. Doesn’t have to be complicated. What are my assets? What are my liabilities? List them all out. This will tell you if you can afford to retire.

Three big questions are:

  • Can I cover my liabilities comfortably on a fixed income?
  • Are my assets easily assessable or will I have an issue with liquidity and monthly cash flow?
  • Can I achieve my retirement goals with what I have available and in place?

Look at all incomes streams that will be available, such as social security, pension or 401(k), personal qualified assets (IRAs, annuities, etc), non-qualified assets (stocks, bonds, mutual funds, and ETFs in a regular brokerage account), bank accounts, home (unless you still have a mortgage), real estate, etc.

This goes back to the issue of timing. If your liabilities could imperil you when you give up a regular paycheck, then you probably need to step back and reassess.

  • Talk To Your People

Hopefully, you’ve already been working with a retirement planner or financial advisor who has helped you create a comprehensive, holistic retirement plan. If so, they will have already discussed issues relating to your actual retirement and beyond.

But now that you are actively contemplating the day you walk in to announce, you should meet them again to let them know. They can give their view on whether you are on track to meet the retirement goals they helped you set for yourself.

If they say you are on track with your plan and should be ready to retire if you’d like to do so, then you can be all the more confident to pull the trigger.

If they tell you that you might want to consider delaying, then you can ask for their advice on how much longer and what to do to ensure you can eventually retire with confidence.

You’ll also want to discuss some specifics, such as what your plan allows for in terms of key issues – how much you can spend each month and in general each year, how much for travel and having fun, health, estate planning, and more.

A big one is ensuring there are assets in place that guarantee that you and your spouse won’t outlive your income.

Additionally, there may be things to be done that they can advise and assist you with that help you adhere to your plan, such as rolling over certain accounts, purchasing certain assets for specific reasons, and more.

  • What’s In It For Me

Next, you want to look at major benefits that may be due from your employers, such as post-retirement healthcare coverage in whole or part.

There are also issues like accumulated vacation or PTO that might be due. Health club, auto club, various buyer’s clubs, and other types of memberships. Basically determine all the perks that might continue and have a clear understanding of what you’ll need to do so you don’t lose them, as well as who to contact if and when you have questions or issues.

Make sure to cover these things with HR well in advance and/or by reviewing your benefit documentation before leaving so there are no surprises.

  • How Much Notice

Okay, you’ve done your homework and it’s time to let the company know. Now you need to decide how much notice you need to give your employer. Simply stated, there is no set answer, so it boils down to what you are most comfortable with.

If you have always wanted to walk in and tell your boss to jump in a lake, then a notice will probably be one day long.😊

But before doing so, you want to have really considered this decision. Yes, it may feel good, but it probably burns a bridge with your employer. Who knows what might happen in retirement? It may be tough to ask for your old job or for a reference in the event you have to go back to work. The biggest question is whether you really want to end your career on such a sour note.

You also need to keep in mind that providing little notice will likely have the most impact on those you work directly with and care about. They will probably have to do your work until someone else can be brought in to take your place.

In general, the longer you’ve worked for an employer and the higher you’ve risen, the greater period of time your notice should encompass. Six months is considered the norm in some instances, with a period of weeks to a couple of months more the norm and generally considered adequate.

Leaving under good terms and allowing your employer to find a replacement, and in some cases even training that person is a good rule of thumb. For some, the prospect of providing consulting services to their ex-employer is a real possibility, so again, it makes sense to remain on good terms.

Words of Caution

Free vector tiny people examining operating system error warning on web page isolated flat illustration.

There are a couple of important considerations when it comes to announcing your retirement.

  • First, once it’s clear you plan to leave, loyalties can shift. While you might feel you are being a good employee by providing a couple of months’ notice to help train your replacement, your supervisor or HR Dept might feel different.

To avoid being caught off guard, you need to be prepared for the possibility you might be immediately released. If so you might be without a paycheck until a pension or other benefits kick in or you are able to start taking distributions from other accounts. That’s not to say forgo providing notice. What it does mean is to be prepared just in case.

  • Second, when a person announces they are leaving for any reason (retiring, taking another job, etc.) those around them start to view them differently. You won’t be part of the team going forward. Even if they don’t recognize it themselves, they may treat you differently. This can even seep into the work you are given – they may begin to partition you from important or longer-term projects since you won’t be around. It’s actually natural, so you shouldn’t let it bother you and you should expect it to some extent.


  • Put It In Writing

You covered the pre-announcement bases and are confident in your decision to announce your retirement to your employer.

There’s one last step before walking in to do so. Prepare a formal letter of retirement that you will give to you supervisor and possibly HR on the day you announce.

It should be short and sweet, providing details such as the date you plan to retire, willingness (or not) to assist with training a replacement if they want you to do so, openness to consulting or doing project work in the future (if that’s the case), and a brief note of gratitude (if you wish to offer one) for having been given the opportunity to serve the company, employees and customers.

  • Let’s Role – Retirement Announcement Day

In advance of the day you plan to announce your retirement, you should contact you supervisor to set up a meeting. Best not to tell them the reason, just that you need to speak.

On that day you meet, you should be straightforward and let them know it’s your intention to retire from the company. Provide them with you formal retirement announcement letter. Don’t be surprised if your boss doesn’t try to talk you out of your decision. You might even receive a tempting offer if you remain with the company.

Providing notice and your retirement letter starts the clock ticking for other processes, ranging from when they need to replace you, the official separation date (which dictates when a pension might start paying out or you receive or stop receiving certain benefits), and more.

How the actual conversation goes will largely depend on your relationship with that person, as well as you workplace in general. You’ll probably know what to expect in advance given your time there already.

Sharing other details is up to you (example – you plan to move to Miami), but you should expect that what is shared is likely to get passed around the workplace no matter how discreet your supervisor is or isn’t.

Keep It On The Downlow

Free vector top secret concept illustration

Which brings up another important point – sharing the news with co-workers in advance. Never a good practice as the news is likely to get out in advance of speaking with your supervisor to announce your retirement.

This can create hard feelings and sometimes serious problems, including immediate termination. Simply avoid the issue by letting your boss or supervisor know first, then sharing the news in a manner you are most comfortable with when it comes to your fellow employees.

A common practice is sending out an email after you’ve announced your retirement. This cuts down on having to share the news with a lot of people individually, instead allowing you to share with everyone (at least in your department) at once. Close friends and associates you can still share with personally.

  • HR – Lots To Cover

You’ll also need to contact HR (your supervisor may do so, depending on company procedures) to let them know formally. Your retirement will be documented within the company’s personnel files. Someone in HR will probably contact you to set a meeting for you to come in and speak.

When you meet they will probably have you fill out a Notice of Intent to Retire or similar document that will provide exact details as to the date you will disengage with the company and other important information.

You will want to discuss and confirm important benefits (when they start, how much, how long they last, etc.), as well as backpay, vacation, PTO, bonuses or other income and remuneration you may be owed. You should also confirm your contact info to ensure HR knows how to reach you going forward.

You’ll also want the obtain important contact info from them, such your 401(k) or pension administrator, health insurance coordinator, etc.

Don’t be surprised if they ask you to participate in an exit interview.


Free vector notes concept illustration

Obviously announcing retirement is a big day in your life, as it should be. To do so correctly takes some and consideration. This can be a bit overwhelming.

But it doesn’t have to be. The aforementioned steps are a good roadmap that will inform you as to whether the time is right, as well as guide you as to what to do and expect. Going through this process can ultimately provide you with confidence in your decision.

As you contemplate everything, feel free to reach out to us to set up a meeting to discuss this all-important decision. Do so by contacting us at XXX-XXX-XXXX.

Let Us Help You Achieve the Retirement You Deserve!

Investment Advisory services are provided through Oak Harvest Investment Services, LLC a Registered Investment Advisor. Insurance services are provided through Oak Harvest Insurance Services, LLC. Oak Harvest Investment Services, LLC and Oak Harvest Insurance Services, LLC are not affiliated with the U.S. government or any government agency. Information presented is for educational purposes only intended for a broad audience. Not an offer or solicitation for the sale or purchase of any specific securities, investments, or investment strategies.
“Peace of Mind,” “Safety,” “Principal Protection,” “Lifetime Income, “Guaranteed Income,” or other guarantees are associated with fixed insurance products. No such language refers in any way to investment advice, investment advisory products, securities, or recommendations provided by Oak Harvest Investment Services. Investing involves risk. Rates of return are not guaranteed unless otherwise stated. All guarantees are dependent on the financial strength and claims-paying ability of the issuing insurance company. Annuities have limitations and are not appropriate for all circumstances or individuals. They are not intended to replace emergency funds or to fund short-term savings or income goals. Lifetime income may be available on certain products through an optional rider, at no cost or for an additional cost, depending on the contract. Insurance products are not insured by any federal government agency and may lose value. By contacting us, you may be offered information regarding the purchase of insurance and investment products.
Oak Harvest has a reasonable belief that this marketing does not include any false or material misleading statements or omissions of facts regarding services, investment, or client experience. Oak Harvest has a reasonable belief that the content as a whole will not cause an untrue or misleading implication regarding the adviser’s services, investments, or client experiences. Please refer to www.oakharvestfg.com for additional important disclosures.