Goals life

Long Range Planning & Vision

April 21, 2021

I received a great audio question recently about long-range planning.

As in: how / when do you think about your vision, your 3-5 year plan, your life’s purpose?

Honestly, the question stopped me in my tracks. Mostly because I don’t think I have done much of that recently. And I really, really should.

Reasons that long-term planning and thinking doesn’t happen:

Being too caught up in the day to day. When each day is really full, it’s very easy to just . . . not think about the long term.

It’s intimidating. And sometimes a little bit scary. Thinking long term brings up thoughts of mortality, of kids growing up and leaving home, of relatives aging.

There is no dedicated time to do it. I mean, one can dedicate time. But how many of us do? I have scheduled personal retreat days before but often one day is just enough time to relax and not a ton of long term deep thinking goes on.

These conversations may be more valuable with another person, such as a partner. And that makes it even harder to coordinate! Plus, when two busy people finally have quality time together, they may not want to focus on these tough questions. (Reason why Josh and I still have not finished estate planning we started about 3 years ago. Whoops!).

Anyway, I don’t have one solid answer here. And I DO think yearly and quarterly planning can be very helpful, and even those are easy to give short shrift. But I was curious if anyone here has ideas about how to set aside time for crafting a longer-term vision, either alone or with others. It is definitely something I would like to do more of in the future.

Of course . . . you can’t predict things like a pandemic (or the Dust Bowl — Four Winds is all about dreams crushed by forces of nature). But having a basic idea of what you are aiming for still seems worthwhile.

Please share if you have any current practices for longer-term planning! This will be part of a future episode and I will give credit 🙂

not super long-range. Also I’m definitely going to fail on a lot of these.


  • Reply Laura April 21, 2021 at 6:54 am

    Writing a List of 100 Dreams can be a fun form of long range planning. You are not holding yourself to any of it, but it is ideas of things you might like to have happen in your future – so that allows for the unknowable aspect. Then as you move into planning the next year or two you can start to pull some of these off the list and put them into action.

    • Reply Lindsay April 22, 2021 at 12:26 am

      I agree with Laura! My whole planning system is pretty similar to yours, with the “nested” lists based on time length (daily, weekly, monthly, quintiles, yearly), but my List of 100 Dreams is the overarching list that I get a lot of my yearly goals from.

      When I was first writing it years ago, I took about a month to brain dump anything that I wanted to have happen in my life in the future that wouldn’t happen in the next year, from the majestic to the mundane. Next, I categorized the list (eg Family/Parenting, Relationships, Career, US Travel, International Travel, Productivity, Experiences, etc).

      Finally, I incorporated it into my planning, so I usually review this list every trimester (I use trimesters instead of quintiles). I don’t hold too tightly to anything in the list, but it is a great guide for finding my yearly goals, and just pointing my life toward the things that make me happy.

      I also have a Vision Board party around Thanksgiving with my family/friends. Some people cut out magazine photos, some write out their New Years resolutions, and that’s the time that I spend more time reviewing the list in detail and choosing a lot of the things off of this list to incorporate in my yearly goals, as well as considering anything to add or take off.

      • Reply Chao May 11, 2021 at 1:13 pm

        I really like the idea of a vision board party around Thanksgiving! I may have my family try that this year.

  • Reply Lee April 21, 2021 at 7:31 am

    So interested to see comments on this question! I am not good at this at all. I think with young kids it’s really hard and it’s important to stay in the moment, somewhat- planning a year out is more than enough! Our kids are teenagers now, and I’m starting to think about the fact that in a few years, we’ll have our time back to ourselves (sort of, I assume we’ll be doing college-y things and trips and all). I need to consider how we want to spend it and also develop some fun, personal hobbies!

  • Reply Gillian April 21, 2021 at 7:46 am

    I have recently decided to seek some career coaching because I am struggling with this question.

    On the personal side I have a pretty clear idea of where I am going. My husband and I sat down a few years ago and mapped out a family mission statement guided by the exercise and Madeline Levine’s Teach Your Children Well.

    On the professional side I do struggle. When one is going through medical training, building a practice and having kids the next 5 years tends to be mapped out in a pretty straight-forward way. But once the practice is built…what then? Hence the decision to work with a coach. Plus coaching will force me to sit down and consider these issues at a protected time.

    • Reply Brooke April 21, 2021 at 10:42 am

      Career wise – I’m really happy in my current level at work – being a first line manager is my jam, and senior management seems removed from the things that drew me to management. I don’t see myself climbing up the ladder. However, working at a large company, there are many different teams I could work in. A while ago, I got the idea from a coworker to have a bucket list of the skills I want to develop, as those are not tied to particular roles and leaves you more open to seize unusual opportunities that align. That was reinforced by an exec during a round table who said he never came in looking to be an exec – he just went to the next role that sounded fun when he’d learned all he could reasonably know in his current role. It’s worked well for me.

  • Reply Kelsey April 21, 2021 at 7:50 am

    A few years ago I loved a strategy that Elise Joy shared of creating a page of paper with different sections for personal, family, career, home, etc (whatever categories you want) and then describing your life as you want to see it in 5 years in those categories. She has an IG Stories video about it that I will link:

    I haven’t done it in a while but as we hopefully emerge from the pandemic, and now that I have three kids!, it would be a great time to revisit 5-year plans and dreams.

  • Reply Omdg April 21, 2021 at 8:06 am

    Eh… after a certain point, it should be ok to get off the escalator if you want to. I mean, go ahead, cultivate goals if it gives your life a feeling of purpose, and something to look forward to. But if you like where you are, is it really a problem to not have a long range vision of your future?

    • Reply Margaret April 21, 2021 at 9:18 am

      I’d say that IS a long range vision for your future! The vision doesn’t have to be different than the current but simply acknowledging that is what you want is a good thing.

      • Reply omdg April 21, 2021 at 10:53 am

        Totally fair! I also think it’s worth reassessing whether you really are where you want to be, and if making changes (major or minor) might improve things.

    • Reply Sarah Hart-Unger April 21, 2021 at 11:18 am

      Interesting! But at the same time maybe I’m afraid I might feel regret if I don’t consciously reassess from time to time?

      Although, supporting your point is that I feel like the last several years (well, besides Covid!) have worked out pretty well even without a vision. And maybe even better in some ways (our move, my PD role). Yet I still sort of crave a regular large scale check-in of sorts. At least in theory. Hmmmmm…

  • Reply Amanda April 21, 2021 at 8:23 am

    I started the year using the Clever Fox Weekly Planner Pro. It has a great template at the beginning where you list how old you will be 1 year, 5 years, 10 years, and 20 years in the future as column headings. The rows are then areas of life and you fill in what you want your life to be like at that given time. It really helped to actually think about these things and pin down actionable goals in each area.

  • Reply Amber April 21, 2021 at 8:40 am

    My husband and I have 4 small corkboards in our bedroom – they represent goals for this year, 5 years, 10 years, and someday. I cut index cards in half and write things on them as we think of long-term goals and I always add the year we started the goal to the bottom corner for reference. We typically have a breakfast date around new years to set goals for the year and at the same time we reflect on the long-term goals and to those or make changes as needed. We see the corkboards daily and it’s a great reminder of what we’re working toward – both long term more serious things like retirement at 50 and more fun adventurous things like traveling overseas in the next 5 years.

  • Reply Kristen April 21, 2021 at 8:53 am

    We do an annual family summit. Choose a beautiful and inspiring spot on vacation…think Italy’s Cinque Terre or the shores of Lake Superior. The vacation mindset combined with the gorgeous scenery sets the tone for meaningful long term planning!

    • Reply Sarah Hart-Unger April 21, 2021 at 9:34 am

      Might be hard to get to Italy right now, but that sounds AMAZING!

      • Reply omdg April 21, 2021 at 10:54 am

        I can say from first hand experience over the last week that unless you have an Italian passport, you’re not getting to Italy right now. 🙂 It’s an evolving situation which will hopefully get better soon, but I’m not holding my breath!

  • Reply Lisa of Lisa’s Yarns April 21, 2021 at 9:13 am

    I feel similarly to a previous commenter who said it is hard to do this when you have little kids and want/need to live in the moment. The only long term planning we have done is related to retirement/making sure we have enough to not need to work in X years. We don’t plan to retire early but we met with an advisor last summer to see how soon we would be more than fine on one income/no incomes. Mostly for peace of mind since we work in a volatile industry. I will sometimes ask my husband where he would want to live after we retire but we haven’t been able to answer that question as it really depends where our boys end up.

    Career wise, I am very happy in my current role and I know I am meant to be an individual contributor. I don’t aspire to keep climbing the career ladder as I feel challenged in my role and know I can continue to grow in my role and be challenged. Sometimes I feel like I am not a ‘go getter’ anymore since I am not trying to get promoted but I remind myself I can still be a go getter and stay in my current role. When I set my ego aside, it feels good to know I can stay in this role and focus on growing the business.

    So long story short, I don’t feel the need to do long range planning but I think some stages of life lend themselves more to that kind of planning!

  • Reply Karen Eyre-White April 21, 2021 at 9:14 am

    I book an Airbnb and take myself away for 24 hours. I find that starting to think things through one day, then sleeping on it and reviewing the next morning gives enough time and headspace away from normal life. That is more for my business and professional goals, but you could equally do it with your husband (childcare permitting!) for personal/family goals.

    I’m a productivity coach (based in the UK) and I generally advise clients that a change of location is needed to get yourself in the right zone for this kind of more strategic thinking.

    Also, think about how you’ll structure the time before you go – nothing worse than clearing the diary then getting there and not making the most of it because you’re not sure what ‘strategic thinking’ looks like. So whether that’s Laura’s 100 dreams or some structured exercise like Kelsey recommends, plan that in advance.

    Always happy to chat goal planning!

  • Reply Chelsea April 21, 2021 at 9:22 am

    As a Questioner, this kind of planning gives me heart palpitations. I can’t escape the “Why should I magically, today, 4-21-21 have all the insight I need to make plans for the next 5 years?” If I say I want to try for a promotion or a new job in 2 years, what does it mean if I find the right new thing sooner than that? Or what if I feel happy where I am and don’t want to move at that time? Same with kids… how could I possibly guess what kinds of activities are going to be interested in in 5 years? They will all be so different…

    I would like to qualify for Boston in the next several years, but I also have to accept that might not happen. It *doesn’t* happen for everyone. I’m not sure that I want to be in my same role a few years from now, but my company is changing a lot internally, and my role could look quite different in that time.

    It’s not that I don’t appreciate or desire personal growth, but I feel like setting myself up with such a clear win/lose situation over such a long period of time would be more stressful than productive.

    • Reply Kathy April 21, 2021 at 10:33 am

      I hear you. A colleague said that her approach to teaching is to make a detailed plan and simultaneously be willing to jettison that plan based on what happens in the classroom. I think the same way about long-term planning. I can think about where I want to be in five years, while also acknowledging that the right plan for my 34-year-old self may not fit my life when I am 39. Or in a running analogy, maybe my goal is to qualify for Boston so I make a training plan. But I have to be willing to adjust the plan based on injury, wildfires and losing a week of training due to smoke, or other unpredictable events. It’s hard for me to make peace with that creative tension between planning and flexibility, but this approach helps me.

      • Reply Kathryn K. April 21, 2021 at 11:12 am

        Very well put, Chelsea. As a Questioner/Rebel this type of personal planning other than at a very high level feels quite constraining.

        • Reply Sarah Hart-Unger April 21, 2021 at 11:33 am

          Very interesting! I can totally see that. (For me it seems enticing but apparently not enticing enough to actually have been doing it …)

  • Reply Lori C April 21, 2021 at 9:32 am

    I never really gave much thought to longer term goals/plans until I did Lisa Woodruff’s 100 day program. The planner has a section in which there are 3 rows of 4 blocks, for the 4 seasons/quarters for the next 3 years. The prompts encourage you to fill in children’s ages, anniversaries, milestones, and anything else you can think of that is coming up in the next 3 years. At the time I remember being surprised that I would be turning 40 (I filled this out in 2017 and turned 40 this year) and that I would be celebrating a milestone wedding anniversary. I don’t know how these things “surprised” me, obviously I knew they were occurring, but something about seeing the dates in front of you and marking down things like “P starts kindergarten” made it a reality that was approaching soon! I didn’t do much dreaming/planning beyond that – I wrote in vacation ideas, and a celebration trip for the milestone anniversary, but not too much more. Looking back, it was helpful because we were able to successfully plan and take a trip to Paris for our milestone anniversary 2 years ago!

  • Reply Teresa April 21, 2021 at 10:07 am

    I think the list of 100 dreams is a decent jumping off point for long term planning. Also Cal Newport uses the word autonomy frequently. I think that is a goal that we are generally all striving (I.e. FIRE). So defining what that looks like personally and how you will get there could be a good parallel approach. Justin my thoughts!

  • Reply Marcia (OrganisingQueen) April 21, 2021 at 10:30 am

    I would invest in a couple of coaching sessions to help clarify your thinking and intentions. A coaching client wanted exactly this outcome in the last quarter of 2020 and I remember thinking it was such a good idea to get clarity on career/ family, etc.

  • Reply Lilia April 21, 2021 at 10:31 am

    I find that some people are inspired by this kind of goal setting and other people are overwhelmed by it. I absolutely adore thinking big and bold, and love talking with people to help them think big and bold too. For some people, that could mean scaling back work and making more time for family/hobbies/themselves, etc, and for other people that could mean crushing business goals, etc. My husband and business partner both get a bit overwhelmed by this kind of goal setting on their own, so it’s a fun day when I get to encourage them to clarify and understand their big life dreams (and then make plans to act on them). Perhaps you need to find someone to help you go through this process — a coach or a friend. That way you put it on the calendar as an actual appointment so it gets done!

  • Reply Kathy April 21, 2021 at 10:45 am

    After tenure, I worked with the National Center for Faculty Development and Diversity. One of the exercises was to reflect on your career as a book with many chapters. They asked participants to spend some time writing about our careers/lives to date and think about past chapters, then look ahead to the next chapter. Some of the goals were to help us identify our new priorities and to remember that we don’t have to do _everything_ on our professional list right now.

    I also appreciate that their approach regularly includes both the professional and the personal. I’ve done a good job of mapping out and meeting professional goals, but I haven’t done as well on the personal front.

    These kinds of exercises have been most valuable to me when I have been in a new role (personally or professionally) for about six to twelve months. I’ve learned the ropes of my new situation, the adjustment period is hopefully over, and I can take a look around at the new possibilities. This has been true after finishing grad school, getting a job, getting tenure, getting married, moving … pretty much any change personally or professionally.

  • Reply Jessica April 21, 2021 at 12:28 pm

    Such a great topic and great comments! It’s interesting to see what different people do.

    I do most of my long-range planning & goal-setting based on my reading. Every so often I’ll read a book that has exercises for that sort of thing, and it gets me to think about it again in a new way. I don’t think it’s necessary to do super often, so this works for me. I also think that doing it during your yearly planning could work well.

    Like other commenters, I haven’t found it all that useful to have career goals past a year or two into the future. My best jobs have been ones I chose because I was currently excited about the job and was open to the possibilities that come up.

    In my personal life, most of my long-term goals are very long term. Bucket list / travel topics, financial planning, etc. So they already get included in my shorter term plans as categories.

  • Reply Jessica April 21, 2021 at 1:34 pm

    On an extremely practical level, I do periodically find myself creating Excel spreadsheets titled “Three Year Plan” or “The Book of Life” to map out the broad strokes of timing future plans. They are pretty basic – just the months of 3, 4, or 5 years down the vertical with as many columns out as there need to be. I like seeing what year my kids will be in school 2, 3, 4 years down the road, how old they will be, and also see the light at the end of the tunnel for long term financial goals (student loan forgiveness dates, loan payoff dates, pension vesting, raises, etc!)

    This isn’t part of my normal planning regime – I usually create one or dig up an old one on the fly! Mostly the impetus is planning the timing of future pregnancies (to the extent that can be planned) around other professional opportunities or big trips. For example, I have volunteered to serve on national book award committees in the past, which involve more than a year’s commitment to the task and at least two mandatory conferences – I could wait until my kids are all grown to volunteer, but I’ve identified a few “sweet spots,” where I could participate without a newborn in the house and fly without being too pregnant, etc.

    I’d love to incorporate more What Should I Do With My Longterm Life?? planning, but it’s hard because it ties in so many different areas of life (work, personal goals, family) and with so many variables (Will we want to move? Will there be a global pandemic? (hahaha) What will be going on with the kids?). I also think I am more of a goal juggler/dabbler than others; it might be easier to check in on longterm goals if my goals were just in one arena.

  • Reply ahealthyslice April 22, 2021 at 7:26 am

    I love long term planning! And long term dreaming.
    David and I go over this together about twice a year in our State of the Family review. We review all our finances (retirement, savings, investment, income streams, net worth, etc), and see where we are on our road map towards our bigger goals, which (stated vaguely) include much more travel and financial independence.
    Talking about these plans keeps the fire alive for us to continue working hard to reach these goals.

  • Reply Jenna April 22, 2021 at 9:54 am

    I have been thinking a lot about this because I have many long-term visions or dreams, but I rarely, if ever actually sit down and map out how to get there. I think part of that is because I am a big believer in day-to-day consistency leading to long term results. For me, as long as I am living my day to day life with purpose and in a way in which I am satisfied, I feel like the long-term goals will be achieved. This even translates to my family and children. For example, I have long-term visions of being a ski trip family — I want to be able to take family ski vacation when the kids are a little older (they are currently 4.5 and 7) so we’ve signed up for a local ski club the last three years, given them lessons and instilled a love of skiing in them. We consistently ski every weekend day in the winter and I feel like in 2-3 years, my goal of heading out west for a ski vacation will be able to be realized. I never actually planned for this; just did the day to day work to get there. Same with fitness. I can have a long term goal of running the Boston marathon when I turn 45 or master certain yoga poses, but if I don’t live my day to day life in a way that supports those goals, long term goals are meaningless. So, I wake up early every day and attend yoga class, and I log the miles every day. I much prefer to set shorter term goals that turn into habits that turn into a lifestyle that comports with my overall vision for myself and my future. Doing something a few times is never going to achieve a long-term goal — its has to be achieved with day to day, week to week, month to month, year to year, and decade to decade commitment.

    • Reply Sarah Hart-Unger April 22, 2021 at 2:36 pm

      Very interesting approach! The incremental workup to skiing is fascinating to me – so many people in FL ski but obviously when they take the kids the first time, most are newbies since weekend skiing isn’t exactly possible around here!! I also want to someday do a family ski trip but would involve beginner ski school. When you go, you will be ready for advanced slopes from the get-go – absolutely amazing!

    • Reply Irena April 27, 2021 at 4:22 pm

      Such a great idea, Jenna! I am kind of doing the same thing when trying to instill the love for winter spots. We do go to ski trips, but the kids (ages 3 and 5) were doing tubing/sledding/snowman building, which is WAY less expensive, and i could fit in maybe one half-day of skiing on a four-day ski trip.

  • Reply Jenn April 23, 2021 at 2:30 pm

    I do 10Q (doyou10q.com) every year and that is about as long term as it gets for me! They ask 10 questions – you fill out 1 each day, usually in September – and then they lock the answers “in the vault” and you get sent an email with your answers the following year. It is mostly reflection on the past year but they do ask forward-thinking questions such as “when you get your answers next year, how would you like to feel?” I also make 10 predictions for the coming year – they can be big like “I will have bought a house in X town” or smaller like “I will have run in at least one 5k race” and coming up with those makes me realize what my overall hopes are for the next year and prioritize accordingly. It’s like a mini word-based version of making a vision board I guess!

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