Making The Most Of Milestones

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I remember thinking when I turned thirty not only that it wasn’t so bad, but that it was actually pretty great.  I felt I’d come to the end of the beginning of my life, had lived it vigorously, honestly, and meaningfully, and as a result was well-prepared to launch forward into the middle of it.  I’d spent most of my life training to be a a physician, had a number of close friends, had maintained good relationships with my family, and was looking forward to starting one of my own.  I felt I was coming into the height of my power and most importantly that I was gradually but steadily growing wiser.  I felt, in short, that the journey, though far from easy, had been thus far truly wonderful.

When I turned forty, I felt largely the same way.  I’d married, had progressed in my career, and was enjoying most aspects of the life I’d spent the previous forty years constructing.  I felt my work was contributive and therefore that my life was meaningful, and even when I grew seriously ill (as I described in a previous post, Overcoming The Fear Of Death), I was eventually able to work through the resultant complications and turn poison into medicine.

Certainly there were losses along the way.  As we age in general we often find ourselves pausing to mourn the passing of our youth as specific losses draw our attention to it:  an unremembered name or a reduced ability to bounce back from illness or injury.  But we also have much to celebrate gaining:  experience, confidence, capability, and an improved lifestyle.  Aging, as a brief moment’s reflection makes obvious, is a decidedly mixed bag.

Which means our experience of it and of passing its milestones can be, like everything, either good or bad.  Yet it seems to me that what determines which it will be is the degree to which we feel we’re living our lives well and with purpose.  It was because I felt I’d done both that turning thirty and forty felt like accomplishments rather than disappointments—like turning points rather than dead ends, each a satisfying conclusion of one phase of life and the exciting beginning of another.  Certainly at each I had a list of things I’d not yet accomplished, but because I was living my life in a meaningful way, I never regretted not yet having done them; rather, I looked forward to doing them in the future.

In general, I’m not one to make New Year’s resolutions, to reflect on the year gone by, or to plan what I want to accomplish in the year ahead, the simple reason being I do those things every day.  Living with purpose has become my best defense against existential angst.  It’s also, I’ve discovered, a good defense against regret (which I wrote about in detail in a previous post, The Faulty Premise Of Regret)—for things left undone simply become opportunities sacrificed for other opportunities more in line with my life’s purpose, and mistakes made simply lessons that turned me into who I am today.

My point, then, is simply this:  milestones happen whether we want them to or not.  How we experience them, though, is entirely up to us.  We’re most likely to experience them joyfully if we live our lives in a way that turns them into markers of our success rather than our failure (even if we’ve recently failed in some way when they arrive, if we’ve lived with the confidence never to be defeated, all failures are temporary and won’t obscure the successes of the past).  If we’re clever, then, we can leverage our knowledge of milestones yet to come to motivate us to live in a way that enables us to reach them without regret.

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  • “I remember thinking when I turned thirty not only that it was bad, but that it was actually pretty wretched. I felt I’d come to the end of the ‘good years’ of my life, had wasted it on work, accomplishments, and unhealthy relationships, and as a result was ill-prepared to launch forward into full-on adulthood. I’d spent most of my life training for a career that was over as quickly as it had begun, had lost all of my close friends, had volatile relationships with my family, and had decided never to have children, lest they wind up as miserable as me.”

    Some people do all the right things, and it doesn’t turn out so great. And the people who say internal attitude trumps external events are likely sitting in pretty damn good circumstances.

  • Thank you, Alex. I really appreciated reading your thoughts on this matter. Several in my family (myself included) are approaching 40, 50 and 60 respectively. I have often wondered how much—or how little—significance to place on these milestones. Living purposefully daily has also made sure I have no regrets and that happiness is not a destination. The “joy of being” and finding precious moments to celebrate daily just means that I have often felt underwhelmed at these big “milestone” events which has left me concerned that I am missing something. I am pleased to learn that is probably not the case. Thanks again for an insightful perspective.

  • I’m somewhat with @downfromtheledge on this. As I read this post, I kept thinking how extremely lucky you were in your circumstances and how few others in the world, even in so-called First World countries, could say the same as you on their milestone occasions. Most people have regrets, handicaps, burdens, struggles, and monsters on their backs. A good milestone is one on which one can claim some victory in some part of the struggle. I love your blog, Alex, but this posting comes off as naive.

    Nomi: I understand your point. I suppose I should have mentioned all the ways in which I’ve failed through the years, how close I’ve come to quitting so many things, all the attachments I’ve lost that devastated me, and all the doubts I’ve felt along the way. I’m well aware I’ve been lucky—perhaps luckier than most when you consider all the evil people do to people throughout the world—but I was hoping to make the point that it’s been my sense of purpose that’s sustained me and ultimately helped me forget the suffering I endured to produce a life that looks so privileged to others.


  • I agree wholeheartedly with you, Alex!

  • Dear Alex,
    I really like your articles. I am only 26 years old. Reading your experiences gives me a wider range of things in life.

    Germio: Nice to have you here.


  • I’m going to be 70 in May and my husband and I will celebrate our 50th wedding anniversary in August. I would like these milestones to be fun and memorable and optimistic…but I’m a little scared.

  • Alex—I feel like milestones are moments in time where we reflect on our (subjective) past experiences; you are right that the attitude with which we reflect majorly influences the conclusion we derive.

    However, I think it is very important to reflect on how we acknowledge a moment as a milestone? I believe it is our FREE CHOICE to consider any given moment in our lives as a milestone. It is not driven by society-driven parameters such as age or by other such norms; it is a purely subjective individualistic notion. Once that kind of free choice is acknowledged and accepted, subjectivity is preserved. It is then, that every person has something positive to reflect on, something to celebrate, something to learn from…in reference to their own timeline. When we put society driven boundaries on definition of milestone and ask everyone to define themselves per those those artificial boundaries we get such varied interpretations (Like what Nomi mentioned…).

  • Thank you so much for your thoughts on milestones. I remember hitting 30 and being so incredibly grateful that I could finally shrug off the disappointments, naivety, sadness, and internal struggle which had punctuated my teens and twenties. As I approach 40 (I’m a little more than 2 years out), I strive to see every day as a chance to delve a little deeper into the richness of self.

    Even when things haven’t gone the way I’ve wanted, each milestone seems to me a little beginning point.

  • At thirty I was just getting started. Fifty was fun but even that is getting a long time ago now. I have been out doing physical things lately cleaning trails and my only “regret” is I seem to have lost some of my energy. Seem to have to stop and catch my breath more than a few years ago. Otherwise life is good and I am blessed with basically good health. I once had a father-in-law (I have had several) who had a sign on the wall that said “it was a darn fine day if he could get up and put his shoes on.” He is long gone but I still work on that premise.

  • We do not know the meaning of this life. And whether we are in any way basically different from other living things, big or small. But I am happy that I was born. Life has been a mixed bag, in the first two phases of my life. My regret has been that I could not realize the potential that I could have easily attained with only a little bit of more effort. My endeavor henceforth, I think, would be to put to use all the faculties I have intact still to do some thing to me, to my people, and my fellowmen across the world, not necessarily in that order, to the extent I can. But my regret would be that I would not be in a position to look back and take stock on my performance in this phase. So I try to take stock on a progressive basis rather than on a milestone basis.

  • Alex, I am 32 years old and a mother of a beautiful daughter and twin toddlers. My daughter approached me with an immense amount of fear of growing up and dying. Since that moment a year plus a few months we both suffer from the same fear. I guess for years I never thought of my existence or perhaps it didn’t mean much to me “as I just went with the flow.” I am currently seeking out a grief specialist to help with her as it seems more consistent in the past few weeks. I’m studying Buddhism and Jesus and am trying to build faith as I feel most days my life depends on this. But I feel there’s a huge blockage. I myself have been in and out of therapy and feel most days like hope and freedom from fear are too far for me to grasp. My child doesn’t know I have any of these fears, my words I provide I try with the utmost compassion and sincerity and to myself I feel as if I’m a fraud. My question is, do you have any advise or guidance that would help in healing for us both?

    Thank you,

    By the way, I’m inspired by your writings.

    Dee V.: I know of no easy answers to your questions. Regarding the fear of death, I’d offer the following: Overcoming The Fear Of Death.


  • Enjoyed reading your blog, Alex, and people’s comments. In particular I liked Shivani’s and the consideration he gives to the importance of our own perspectives on what is of value rather than society’s.

    Whatever pain any of us may have had in the past, it is now gone, and I would like to approach my life with each moment being equally precious whatever is happening or whatever I am doing. Eckhart Tolle teaches about “living in the now” or the present moment, and if we can do that, then truly a new day dawns and life becomes tremendously exciting.

    As I say, that is my aim; it is not so far my own experience.

    But if I am to choose a way to live, that is it. Not to live in the past or the future, but in the present—for only now is real, and we cannot live anywhere else in reality. If we spend time assessing our achievements or failures or spending to much time designing future goals, we live in fantasy.

  • I’m a bit late in reading this blog, but I wanted to respond to DownFromTheLedge’s comment. I just turned 31 this weekend and was pleasantly surprised to have very similar feelings to Alex’s. Many people look at me and can say, wow, you are so lucky to be where you are and have the life you have. What’s interesting though, is that only my closest friends know what I went through to get where I am. It was not pleasant or lucky. My closest friend is from a 3rd world country and shocked me once when she told me should would never have traded her childhood for mine.

    Certainly, good fortune plays a role in success, but it is not the only factor. I would rather say that at age 31 I’m finally enjoying a sense of fulfillment because of what I went through, not in spite of it. DownFromTheLedge, if you dismiss the role that internal attitude plays, you may be missing one of the few, if only, things in life that you can actually do something about.