ten questions to retire early

Our Next Life // Early retirement isn't for everyone. We've put together this list of 10 critical questions you should be able to answer before you retire early, to help you decide if early retirement is right for you.

let us dispel a big myth right now: early retirement is not for everyone.

early retirement won’t magically fix everything we wish was different about us or our lives, and it comes with its own set of pitfalls and stresses. to some of us, those things are worth it, but we can only know that if we do some real introspection and planning. and not just financial planning, but also planning around personal fulfillment, health and self worth.

to help sort this out, we’ve put together a list: the ten questions you should be able to answer before you retire early. no matter what stage you’re at in thinking about or planning for early retirement, take some time to think through these questions and their answers. if you struggle to answer any of them, then early retirement may not be right for you, or may not be right for you right now, and that’s okay! not everyone has to share this vision for their future. particularly if you don’t have a clear vision of what you want to retire to, there’s nothing wrong with working a little longer, or even a lot longer. not liking your job — being clear on what you’re retiring from — is not enough of a reason to retire early. the answer may be much, much simpler: find a different job, or a different career path. if you’re committed to retiring early, but don’t have good answers for all of these questions, then let them kick start some additional thinking and planning that will pay off once you pull that ripcord and wave arrivederci to your career.

// the ten questions to answer before you retire early //

1. how will you support yourself or your family without a job? (and will that change over time?)

the answer could be any number of things — earning dividends from stocks you own, selling shares of index funds, collecting rent on an investment property or ten, doing part-time work, or some combination of the above. the answer can also change over time, focusing primarily on one strategy until you reach age 59 1/2, for example, and then shifting to live off your 401(k) or ira after you reach the eligible age.

our income plan over time:

Income Over Time

other pieces to consider: will you follow the 4 percent rule? have you put together a realistic budget that will account for all potential expenses and things you want to do in retirement? have you done multiple projections to ensure that you’re saving enough before retiring to provide enough income for the full period that you’ll need it, even if the markets don’t provide good returns every year? if you have kids, will you plan to pay for their college?

2. what is your backup plan for dealing with financial emergencies or hardship?

how will you make sure that your whole plan doesn’t get sunk, especially after you’ve given up a well paying job, by a natural or financial disaster? will you budget for homeowners or renters insurance? will you maintain an emergency fund, separate from your other investments? will you carry life insurance? will you build in any other contingencies like the ability to downsize a home or move somewhere cheaper? how will you ride out bad periods for the stock markets, including possibly extended recessions? how much of a cash cushion will you maintain? could you trim back your early retirement budget if you had less to spend some years? a full rundown of our contingency plans are here.

3. how will you get healthcare?

it’s no secret that healthcare costs bankrupt people all the time. how will you ensure that that never happens to you? will you buy health insurance through the federal exchange (or your state’s, if they have one) until you reach age 65 and qualify for medicare? have you done the calculations for the income you plan to have, and ensured that your retirement budget can cover the full cost of premiums and copays (as well as the possibility of needing to go up to the out-of-pocket maximum)? will you plan to live abroad and avoid buying insurance under the u.s. individual mandate? (or are you a lucky canadian, who doesn’t have to worry about such things?)

our healthcare plan over time:

Healthcare Over Time

4. how will you keep your body and mind healthy?

what is your plan for eating healthily, exercising and stimulating your mind in early retirement? does that plan look a lot like what you already do now, or does it involve some drastic changes? as maggie would say, early retired you is still you, so ask yourself if drastic changes are really realistic, or if you need to start making incremental changes now to make sure staying healthy is doable once you’re retired. on the mental front, will you embrace new technology and other societal changes as you age? will you befriend younger people? will you engage in activities or hobbies that expand your thinking, and force you to form new neural pathways?

5. what are you retiring to?

this question is perhaps the most important of all. nothing is worse than saving for years to retire early, burning bridges in your career, and then discovering that you’re bored. consider well before that happens what you will do with your new-found time in early retirement. what will excite you about getting out of bed every day? how often will you check things off of your bucket list? what do you want your contribution to the world to be?

6. what will your living situation be?

do you plan to stay put where you are for retirement? do you plan to move into a smaller home that’s easier to maintain and which frees up some capital? do you plan to relocate? do you plan to go nomadic and live the rv lifestyle? for aspiring rv-ers, do you have a plan for if or when you decide you ultimately want to put down roots, and now need to pay rent or buy a home? for those planning to live in a home, will you pay off the mortgage before you retire, or keep paying it off in your retirement years? if you plan to keep paying off the mortgage after you retire, have you considered the health insurance subsidy and tax implications of needing enough income to make your mortgage payments? have you budgeted adequately for miscellaneous housing expenses like property tax, rent increases and utilities?

7. what do you want a day in retirement to look like?

what will an average day in your new retired life look like? what activities will you do every day? how will you spend most of your time? will you spend a lot of your time surfing the web and watching tv? when you look at your vision for each day, does it sound both realistic and fulfilling to you?

8. what will your social circles and interactions be like?

who will be your primary friends once you retire? will you be able to see them more often, or will their work schedules prevent them from spending time with you during your new free time? how will you make new friends? if you have a partner, do the two of you plan to spend most of your time together, or apart? will you have your own hobbies, or share most of your hobbies with your partner?

9. how will you and your partner, if you have one, stay on the same page about money and life goals?

are you both equally committed to retiring early, and do you share the same vision of what’s worth sacrificing to reach your goals? have you mapped out your big goals for your lives together? do you both feel comfortable with your retirement budget and projections, or does one of you feel they are too aggressive or risky? are you both committed to the discipline and frugality needed to ensure you don’t outlive your retirement savings? do you regularly check in with each other to make sure you’re still on the same page about money and life goals? if you’re currently single, does your vision allow for flexibility if you one day get in a serious relationship?

10. how will you define yourself and derive self worth post-career?

once the title is gone, how will you see yourself? what will you do to ensure that you see yourself as a worthy person making contributions in the world? how will you find fulfillment without a job? how will you give back? what will you want to have accomplished, looking back on your life at age 80 or 90?

9 thoughts on “ten questions to retire early

  1. Great questions! It’s funny but I’ve never thought of “retiring” as “not working” to me it’s just “not working for someone else!” Three years ago my job ended (I was one of the last six employees in a wind-down operation). I haven’t had an earned income since but I’m definitely not retired!

    I’ve spent the last three years working to build my own business. It’s a long hard slog but so worthwhile. Truthfully, it doesn’t pay my personal bills yet but it does pay for itself and it funds new ideas as I’m trying to find my “thing that works.”

    Because I saved hard during my working years and paid off my mortgage, my expenses are relatively low so I’m able to live off my emergency fund. If the universe smiles on me, I’ll be able to replace my old earned income with my business.

    If someone who plans to “retire” early isn’t committed to using their time in a productive way, I think you would get bored pretty quickly. There’s so much to learn and do but as you suggest, you need to figure out what it is that interests you…what you want to build…how you want to give back.

    Here’s wishing you great happiness and fulfillment when you set out on your early retirement journey!

    Liked by 1 person

    1. Hi Ree — Thanks for commenting! I think when we say we don’t plan to work, it’s really saying we don’t plan to rely on an income. We are not the types to sit still, so retirement is a chance to work on our creative projects and do lots of mountain climbing expeditions, travel the continent and world, etc. We’re starting to rethink the work question a little bit, but the major point is that we don’t want to HAVE to earn money, so we can do what brings us joy instead of worrying if it will sell. But I love that you’re focusing on building your own business, and I hope that you find lots of success with it very soon! :-)


    2. So much you say is right on. I’ll be retiring in a couple more years and it’s not that I won’t be productive anymore. It’s just that I won’t have to work the Monday through Friday routine for somebody else. I’ll be able to do what I want which is going to be a whole lot of things. I have no doubt that my day will be full and productive. For me. And along the way, I’ll find a way to earn some income to supplement my retirement income to make more things possible.


  2. It doesn’t come without fears. My firmed shut its doors last June, I saw it coming, and was totally financially prepared for it and ‘retirement.’ It is a cliche, but living the social interaction, the sense of self as a professional, to say nothing of income and benefits — though fully anticipated — hit hard. I’m still reeling even though I’ve stayed active in my industry, taken on post that allows me to work from home, not fully full time, and pays some bills. But daily I ask, ‘now what?’ Classes? Yes. Travel. Yes. For me, leaving the job allows me to be the student again to feel the excitement, and yes fear, of starting something new. Maybe being such a student will stave off some of the aging process. I emphasis it is a process and the loss of a job, status and benefits that go with it, is not easy no matter how prepared you are. And while it would be great to have a new purpose — get a Phd, write, start a fun business — it’s hard to connive that after working full time. So for me, others, give yourself the time. Be patient and just know that…ah there I felt it, a twinge of fear. But it is a good fear I think.


  3. I see there at 10 questions to retire early on your list. I am here to tell you there is only one question that really makes any difference. That is health insurance coverage. If you don’t have it, you can’t quit work unless you are worth tens and tens of millions of dollars. I have been in a position that I could have retired for quite a few years now. I say this based on all the early retirement blogs. But I was smart enough to know that this ACA Obamacare was going to fail. So I kept holding on to the job and it seems one way or another the ACA will either be collapsing on itself or it will be voted out. Either way, it needs to be gone and a new plan figured out. I read all of these early retirement type of sites. I read about some people who claim to have retired but they are still on the health insurance plan of a working spouse. What a joke. It just means your spouse is the one who is working to support their easier lifestyle. Some I have emailed to ask how they “retired early” advised they just don’t even buy health insurance and take a chance.

    So i am trapped and continue to work in a very lucrative job for more than 25 years.. that I desperately want to exit. Lets all keep wishing and hoping for something to change, but I am guessing the entire healthcare system implodes upon itself along with a lot of other things before you can “retire early”.


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