One of the hardest things to do is create a vision for your life.  After all, it’s your LIFE. Your whole life. With school and work and friends and family and loves and fun and hobbies and EVERYTHING.  And where do you even start?

Most people I know start filling up that blank slate of “what do I want to do with my life” with things they’re supposed to want.  They put in the big life blocks they’ve been trained to think about, like schooling and degrees, jobs and titles and career progression, meeting a life partner, having children, buying first houses then second houses, planning for kids’ private schools and colleges, and retiring early with enough in the bank to never have to work again.

And they attach dates and timelines to each of these activities.  I was having drinks with a friend one evening, and she was panicking and sharing that her life plan was off track.  She explained that in order to have two children by the age she planned to have them according to her life timeline, she needed to meet someone, spend two years dating him, then get married and spend at least one year married without children, and then nine months for the first baby, then a year, then nine months for the second baby, and boom – she needs to meet that special someone like… TONIGHT IN THIS BAR… or else her vision for her life and the timeline she had created for herself would be broken.  I remember thinking, “Oh my dear friend, maybe your life won’t go as you’ve planned but maybe it will surprise you and be even better than your plan. Leave yourself open to that possibility instead of staying so focused on something that may not happen (like meeting that special someone TONIGHT) and missing the enjoyment of the evening and of your life more generally.”

The fundamental problem with the approach taken by most people is that the slate gets filled up quickly with those big blocks of things they’re supposed to be doing and the vision seems full (overwhelming even) with no room for anything else.  With a full slate defined, they set off on a path of pursuing those things that they’ve been taught to want. And they haven’t even had the chance to think about what they really want, much less explore it.

Then a few years down the road of pursuing this vision that was filled with things they were supposed to want, some reflecting happens and people realize that many of the things they put on their slate, they didn’t even want in the first place.  They were expected to want those things but it wasn’t really for them. But now they’re in a place where they have a mortgage and bills to pay and maybe a spouse or children and people to whom they’ve made commitments and unwinding it all to go in a different direction seems more and more difficult.  

And as a result, they’re missing the joy in life.  Because the plan did not include time for surf classes or to learn to play the guitar and write music or to play with their dog.  The plan did not include tending to the garden or learning a language or having relationships big and small (of the meaningful and pointless varieties). The plan did not include job shifts or new opportunities and paths.  Because joy wasn’t in the plan, they miss the opportunity to grow, to expand, to change as they’re vigorously pursuing the vision and plan and timeline they created for themselves based on the pursuit of things that they are supposed to want according to other people.

Sometimes we need to remember that we are natural creatures.  And in nature, there is life and growth and loss and hibernation and rebirth.  No one ever seems to put divorce, the illness or their child, getting laid off, or their parents’ passing in their vision or plan or timeline but those things are just as real and just as much a part of life as other things they do put in the plan.  No one includes the chance encounter in an airport with a perfect stranger who changes your whole life with a few words and a new perspective. Or the way a movie can touch your soul and make you cry. Or the raucous laughter – the hoots and howls – with your friends.  Or the deliciousness of staying out dancing all night and watching the sunrise on your way home.

When I think about my own life, in my 20s, I was definitely pursuing the plan with the timeline and all the big blocks of school, work, marriage, and children in my line of sight.  Then when I was 31, it all came crashing down. Hard. And it felt like I was in a blender for a few years, not knowing which way was up or if things were going to be ok. And because all of the big blocks I’d built my plan around had basically evaporated, I had to start over.  There are no words to describe how brutal it was to have my vision and plan and timeline destroyed and have to create a new one.

Because I had to, I thought more about designing the vision in the first place, giving myself permission to include more aspects of my own joy and growth at the forefront of the vision and plan, giving myself more flexibility on what kinds of relationships I wanted to have and what I wanted from them, and learning how to fit work around those other things instead of putting work smack dab in the middle of it all.  

Do I “have it all” as others think I’m supposed to?  Nope. But I have what I want. After all, why would you pursue what others think you should want?  Why not just pursue what you want instead?

So what’s my advice?  

First and foremost…

When you’re creating your vision for your life, ditch the timeline.  Measuring yourself against an externally-imposed timeline (whether it’s imposed by you or by someone else) is the best way to let life pass you by.  Also, when you’ve set a timeline for yourself, whenever the unexpected happens – whether they are positive things like fun and surprise and opportunity or negative like loss and struggle – you feel like a loser because you didn’t hit a milestone by a specific date.  Take the pressure off by removing the timeline.

This is really difficult for most people because we are taught to think in terms of timelines.  Get a driver’s license at 16, finish high school at 18, finish college at 22. Then our timelines tell us by what age we should get a job and an apartment, buy a car, be in a serious relationship, get married, have kids, reach management and leadership levels at work, hit financial goals, buy a home, and do all of those other things we think we’re supposed to be doing.  But stepping back, ditching the timeline, and thinking more about the stuff that matters will lead to a more fulfilled and fulfilling life.


Get focused on the stuff that matters.  Get focused on what brings you true joy – like petting your dog or feeling the wave rise up under your surfboard or creating something beautiful.  Make sure your vision and plan include plenty of time for that.

Get focused on where you want to grow and have experiences – like learning a language or traveling to new places or learning to code or to cultivate a vegetable garden or dance or laugh or challenge yourself intellectually or at work with new assignments or writing a screenplay.  These can be things that enhance your life both personally and professionally – they go together – because the ways you want to grow in life will help you grow professionally.

Then get focused on the kinds of people you want to do this with.  Not specific names but qualities of people. Those who are supportive of you and who accept you for who you are and who will accompany you in your pursuits of joy and growth.  Then go find more of these people and surround yourself with them!

And yes – we all have to pay our bills – so get focused on what that equation looks like.  But only after you’ve thought about where your joy comes from, what kinds of growth you are seeking, and what kinds of relationships you want to invite into your life.  Fund those things first and then think about how big your house needs to be and what brands of clothes you want to buy.

And yes – difficult things happen.  It’s part of life. So leave room for that and be kind to yourself when it’s happening.  Take the pressure off of yourself at work while you deal with health issues that arise more and more often with each decade you pass.  Know that everything will seem to stop for a year or two when an important relationship in your life ends abruptly from death or divorce.  Know that your career will ebb and flow and not always move straight up a ladder as companies grow and shrink and as industries appear and decline.


Give yourself the freedom and flexibility to continuously adapt, update, revise, and change your vision and plan.  Like with a garden, you plant, things bloom, you prune, and things grow in new ways. Over and over. Let your vision and your plan grow and also prune them and plant new kinds of flowers over and over so that your vision and plan adapt and change to fit you rather than sticking rigidly to a vision or a plan that no longer fits.

And finally…

Don’t compare yourself to others when you’re trying to figure out if your life is going how it needs to go.  You’re living your life. Other people are living their lives. Comparisons aren’t valid because you’re apples and they’re oranges.  You can both be awesome at the same time. Instead, stay focused on what is right for you and let the external pressure to measure up to others fall away.  It’s easier than it sounds but remember that your life is not about playing someone else’s game so don’t measure yourself by their rules and standards of success.  Design and play and win at your own game instead.