Paul McAleer: Hi. You’re listening to Designing Yourself. My name is Paul McAleer.
Whitney Hess: And this is Whitney Hess.
Paul: Hi everyone. This week we’re going to do another big topic. I’m not going to lie. It’s a big topic. It’s regret. We were basically provided this idea by Ryan MacMichael, who’s a longtime listener, first-time submitter of topics. And he really wanted to know what we think about regret. So, I’ll open the floor to you first, Whitney. What do you think about regret?
Whitney: Well, firstly, thank you so much, Ryan, awesome fan that you are, for providing us with a topic. We’ve been wanting other people to give us topics for a while. We could come up with them for forever, but we decided early on that we weren’t going to be too purposeful with the order of our topics. We were just going to let them flow naturally.
And it tends to be something that’s coming up for one of us during the week that we record. And so, we say, hey, how about we do a podcast on this? But I’m thrilled that we have one from Ryan. And so, for the rest of you listeners, if you do have topics to share, please make sure that you email them to us, Tweet at us, smoke signals, whatever. And we’ll give you all the ways in which you can do that at the end of the episode. So, regret?
Paul: We have no regrets about that, no regrets about that at all.
Whitney: No regrets?
Whitney: OK. Well, my whole growing up, you know those times that you’re sitting around the campfire with your friends or you’re playing Truth or Dare or having philosophical conversations and someone asks you what’s your biggest regret? Have you had those moments?
Whitney: Well, my whole teens and early 20s, my line - and I really felt like it was a line because I was ready for it whenever someone asked - was that I don’t regret anything I’ve done. I only regret things I haven’t done.
And I think I mostly feel the same way now as a 31-year-old. But I lately and starting to feel as though it would be OK if I did have some regrets about things I’ve done. I think I held that view for so long because I wanted to believe that everything I’ve done in my life has served its purpose, has gotten me to where I am now, that even if it could have been seen as a mistake, even if it was something that I felt badly about or I mistreated somebody or I would have done differently if given the chance again, that I didn’t want to regret it because that would mean not having learned its lessons.
But I’m recently starting to feel as though regrets aren’t so bad. And I think that’s in part due to the development that I’ve been going through as part of my coaching program. And I think I mentioned to you last week that one of the things that we did for each other in the first session was write each other these slogan cards, kind of these sayings that can help keep us on track for where we’re trying to take our lives, things that we can reread and remind ourselves what we’re trying to achieve. Did I mention that?
Paul: You know, I don’t think you did. It sounds awesome.
Whitney: Well, I brought up the compassion card, and that was this laminated card. But at the same time we have these index cards as well. And they were handed out initially by our instructors, not handed out but we sat around the room and they spoke them and then we wrote them down on cards.
And one of the things that was given to me by the instructors was regret is not an end. It’s a new beginning. And I think that has shifted my perspective on what regret really means, that it’s an opportunity to say, you know what? Who I was then when I did that thing, it’s not who I am anymore, and recognizing that I’ve changed, that I’ve evolved, is going to allow me to start fresh and be the person I am now.
So, I’m grappling with it still, but I think that my views on regrets are evolving.
Paul: Yeah, mine are as well. I like the idea of them not being so bad. I kind of had a different experience than you when growing up. And the way I felt about regret is that I always had things that I did regret doing. And there were, of course, some things as well that I regretted not doing. I mean, both kind of coexisted for me. And these were things that I carried around for quite a long time.
And that was also something that I would allow to permeate my thoughts now and then. And I’d just kind of relive those things in not a great way. These were not things that were overly positive. But my attitude toward them has shifted fairly recently as well in that I’m not seeing as much regret in these decisions and non-decisions as I once did.
Really, what I see when I look back at any of these things is that was really who I was at the time. That was the best articulation of me at that time that I was aware of. And I have to respect that and acknowledge that because, yes, there are times when I could have done something else. But every moment is that way, every single moment.
I mean, I have that choice right now. And there are tons of things that I am not doing. And I don’t know if it’s my ignorance playing into this, but I don’t regret not doing those things right now. There are some things that may tug at my brain and pull me into monkey mind a little bit. But all in all I could almost see it as being that if I wasn’t doing what I either should be doing or could be doing within any moment I could be regretting that I am not doing those things or not not doing those things.
I like the idea of regret being a beginning, but I’m also - I’ve always had trouble with people who say no regrets at all because to me that feels fakey-fake. And I don’t know if it is, but that’s how it’s felt to me, just that it didn’t seem possible. It’s like, how can you not have regret? Come on. Everybody’s got some sort of regret.
So, where I’ve gone with it in general is a little different from you in that I have gone to a place of not seeing it or portraying it as regret at all. And I guess that means that I’m one of those fakey-fake people who says no regrets.
Whitney: You're not fake, but I have had the same feeling or kind of like ickiness about that saying, no regrets, for I think a similar reason to you, that it feels as though the person isn’t willing to look back on their life with any critical eye or that they have no ill feelings about treating people poorly or having made bad decisions in their lives and as a result have had no growth.
I think that’s how I always take no regrets. But now that I’m hearing you say it in the context of there are a lot of things that I did regret. But now that I’ve looked back on them I’ve realized the purpose that they’ve all had in my life, and I’m not going to be angry with myself for experiencing those things, then no regrets actually makes a lot of sense to me.
Paul: Yeah. It’s fakey-fake.
Whitney: It’s not fakey-fake.
Paul: It’s not. It’s not. It’s not. But I agree with you. It’s the idea that regret as a concept isn’t necessarily something I really want to invite in my life much anymore because I don’t see it as a really positive thing.
It goes hand in hand with the fact that all of the things that I’ve experienced in my life have led up to this very moment, and that happens all the time. And, sure, there are things I would have done differently. I think almost all of us have maybe some part of us that really says that and feels that way, big or small.
But I don’t see that as regret for what actually did happen. I see those things coexisting just fine. Yes, there are things that I would have chosen differently on. But that doesn’t mean I would want that so much that I cannot see what really happened and also how that contributes to the way I am now and the person I am now and the person I could be as well.
Whitney: I think it’s really interesting that you brought up regret being this kind of negative thing because I didn’t tell you this, but when we first got the note from Ryan that we should cover the topic of regret and we were talking about doing it, my gut reaction was, but all of the topics that we’ve covered so far have been positive. Do we really want to cover a negative topic for our 10th episode?
And I decided, you know what? It was the right thing to do because it’s, first of all, from Ryan, who we appreciate tremendously.
Paul: He’s wonderful.
Whitney: Very wonderful. And secondly, that it feels very relevant to the conversations that we’ve been having already. So I thought, you know what? Great topic. But there was a little part of me that coming into our chat today felt, you know what? We talked about self-awareness - very positive.
We’ve talked about overcoming fear - very positive. We’ve talked about compassion. These are all such positive things. And regret sounds so doomsday to me. Just in the word I feel as though it holds a lot of negativity. And maybe that needs to be something that we overcome or that we do away with, this idea that regret is bad, regret is wishing you had done something differently and wanting to go back and being upset that you now have to live with the way in which it occurred or the way in which it didn’t occur, as the case may be.
And so, I was wondering, what do you define regret as? Because I consider it to be a dissatisfaction or an upset with an experience in your life, whether it happened the way you wanted to or it didn’t happen the way you wanted to. And it’s a little tug that follows you into the future that makes you feel negatively about the past. That’s how I have always seen regret. But how do you see it?
Paul: I really like this personification of regret being this thing that tugs at you and follows you into the future. That is a strong, strong image. Mine is not that visual, I suppose. But the way I have defined it is, and really thought about it, is that it is an event that occurred in the past, and it could be the very recent past, it might have been a moment ago, that really I have an incredible desire that that event had a different outcome or did not happen or happened in a different manner.
Basically, if I had more presence of mind to act in that moment the way that would be a really good articulation of my whole self or how I needed to be at that time, then that’s what I wanted. And then for me it comes along with - I’m actually moving my finger around in a spiral going down because it’s kind of it goes along with things like, well, regret, and there’s a little bit of shame and confusion and concern. And that’s how historically I’ve thought about it, too.
So, those things are really tightly tied with it. And you’re right in that it’s kind of a negative thing, too. I think it is. I mean, I don’t know if there’s any really good connotation for this thing.
Whitney: I wonder if there’s somehow a difference between having a regret, meaning recognizing that you had disappointment over the way something went down in your life, versus allowing that situation to become a burden.
Paul: Oh, that’s good.
Whitney: Like, I wonder if regrets can be lighter weight than we tend to talk about them.
Paul: I think so. I think that’s a really good point because - gosh, more food, less UX. I regret a little bit the lunch I had today, just a little, because it wasn’t terribly satisfying for me. But I ate it and so be it. But that’s not something I’m now carrying around with me and really - I was able to call it up really quickly, but it’s not something that I’m actively thinking about and been thinking about for the past eight hours or so.
I haven’t been letting it really occupy a lot of space in my mind. And it’s not a significant regret. I mean, for me the significance maybe is something interesting there, too. And maybe that’s where it’s just having a regret versus, as you say, allowing it to become a burden, because I think that’s a very fine point.
So, at what point does it become something bigger than, man, you know, I could have or really should have, by my own standard, chosen something different for lunch today, which I kind of regret a little bit? But it was tasty, so I don’t regret that.
Whitney: I mean, hey, I’ve had that experience, and I bet we all have with food, with conversations. You walk away from a conversation and then only later do you realize, oh, that would have been a great comeback. Or, you know what? I should have said this instead of that, or I can’t believe I put my foot in my mouth in that way.
I think we all experience that. And there’s comedies based on these kind of social errors that are made. And we can all laugh about them. But I think that when you start to get into a blame game, like when your inner critic really starts to rear its ugly head and you feel guilt and shame, as you said, around how you mistreated someone or how you misspoke or how you choose Door A when you should have chosen Door B, and you don’t accept that what you did was what you did, even if you do feel a bit of disappointment over it I think that the feeling is OK so long as you don’t start screwing up the future by harping on the past.
And one thing that I’m reminded of immediately which you may find this very strange, but here’s my non sequitur, I’m thinking about the days of atonement, which in Judaism is the 10 days between Rosh Hashanah and Yom Kippur. And the reason this comes to mind for me immediately, and I swear to you I didn’t think of this before we started talking, it’s only coming up right now, it’s these - so Rosh Hashanah is the new year in Judaism.
And unlike in Catholicism, for instance, Jewish people don’t have the custom of atoning for their sins, going to confession on a regular basis. Instead, what we do is we do it once a year. So, at the beginning of these days of atonement, the period of the new year, Rosh Hashanah, we begin to reflect upon all of the things that happened to us in the prior year.
And it could be the business decisions that we made, the way that we treated members of our family, the way that we treated our bodies - so, I wish I had eaten something different for lunch, our self-care, our emotional state, that inner critic rearing its ugly head, the people that we’ve wished harm to, the people that we knew we could have helped but we didn’t, all of those things that I think would commonly be referred to as regrets.
You’re meant to reflect on those, bring them all to mind and make amends. And how is it that you make amends? Well, I think that for a lot of people that means asking for forgiveness. And sometimes it does include that. So in this 10-day period that you have, you have a chance to make phone calls, see people in person and essentially say, you know what? When such-and-such happened I’ve looked back on it and I would have behaved differently if had a chance to do it again, so do I have your forgiveness?
Now, that’s kind of the more direct way of getting forgiveness, but the harder forgiveness to obtain is when you have to give it to yourself. And it’s kind of a little bit of a running joke in Judaism, I think that at the end of these 10 days when it’s Yom Kippur you fast for a day so you abstain from eating, the intent being that you are every time you feel hunger reminded that you’re fasting with the purpose of atoning, that you are repenting from your sins from the previous year, you feel a tremendous amount for hunger.
It’s a very simple thing to give up considering all of the things that you’ve done poorly in the previous year. So what’s one day of not eating? And at the end of the day you know that you’ve been forgiven by God, by the universe, by whatever higher power you answer to. It’s kind of silly because we don’t have a figure like a priest to say 10 Hail Marys.
There’s no human being that’s telling us that we are, in fact, forgiven. But it’s our custom. And in some sects of Judaism there’s this saying on Yom Kippur because it is a very somber day. You’re bringing all of your sins to light and you’re atoning and you’re grieving for the death of those who’ve passed in the previous year and whatnot.
It’s not a happy day. So, people don’t say Happy Yom Kippur to one another. But the greeting is, have an easy fast. And that essentially means there’s a belief - folklore or something - that if you’ve had a really difficult time not eating that day, then you had a lot to atone for.
But if you had an easy fast, then you weren’t that much of a sinner and you’ve been forgiven and all those ills have essentially passed through you and now you have a totally clean slate with which to start your new year. And I always loved that aspect of it.
And I’m not terribly traditional in the way that I observe Judaism. But I have always fasted on Yom Kippur, and I’ve always taken those 10 days very seriously in thinking back on what I regret.
But I have rarely reached out to others to apologize for what I’ve done, to make amends. And I’m thinking back on it now. Why is it that I’ve done that? And I think that ultimately the person that I’ve needed to make amends with the most year after year is me.
And so I don’t really have anyone else to feel sorry for. Yes, I’m sure that I’m bitchy to people unnecessarily at times. Yes, I’m sure that I’m short-tempered with my boyfriend or with my parents. I’ve probably made a zillion mistakes with my clients and have learned from them.
So, a part of me feels as though I don’t need to go back and apologize later. I probably apologize in the moment when I realize that something has gone wrong. But I don’t think I’ve done a lot of reaching back into the past and pouring salt on a wound or whatever, opening up those past harms to apologize for them. It’s often me who can’t let it go, and I’m the one that I have to find that solace with.
Paul: So, how do you do that? Because, that to me is one of those things that’s easier said than done. Because, I have been in the place where I will remember a moment and then I will kind of replay it in my head a little bit and allow myself to do that. So, essentially, like you’re saying, pouring salt on the wound there. I will do that. I don’t do it as much, but I still do.
And it’s kind of like this really - it’s kind of like watching a really not great movie. You know what happens. You’ve lived it. You know what happens, and you’ve kind of allowed yourself to re-experience it in a certain manner.
So, what are the things that one can do to learn to atone and forgive oneself and/or let it go? All sounding very simple when you ask a question, right?
Whitney: No. I hear you. I feel the same way, that it’s a lot easier said than done. We are our own worst critics, all of us. And we can separate ourselves from negative environments. We can leave a bad job. We could leave a bad relationship. We could end a friendship. There are a lot of things that we can do to get ourselves out of bad situations. But at the end of the day, we can’t get out of our own heads.
Whitney: And so, that blame and that shame, it’s really poisonous because it’s not as though it could be compartmentalized. When we feel those regrets to an extreme extent and we won’t accept that what happened in the past happened and we’ve learned a lesson from it and so we’ll do things differently in the future, when we just won’t let it go we are short-changing ourselves and we are preventing positive things from happening in the present moment because we are living in the past and we’re living in this really negative state.
I mean, immediately I’m reminded of the musical Rent. Please tell me that you’ve seen it and/or heard the soundtrack.
Paul: No. And as I said that a crack of thunder just happened outside.
Whitney: Oh my gosh.
Paul: I mean, I’m familiar with it from a basic pop culture perspective, but that’s about it.
Whitney: Well, I will educate you at another time because it really is a sensational modern musical which is really a modernization of La Boheme.
Whitney: But anyway, not going to get into it now. But there is one line in the show that for some reason popped into my head. It’s forget - now it’s a tongue twister. I’m not going to be able to say it. Forget regret or life is yours to miss. And that came to me hearing you speak about this idea of not being able to move on or allowing that stuff to continue to - I like how you call it monkey mind, but just turn over and over and over in your head.
And I think that what happens then is that you’re making a bad situation worse. Not only did you screw something up in the past, but you’re screwing it up in the present, too, and that’s going to have a very negative effect on your future.
So, I think that the only thing that has worked for me - and it doesn’t work often. I’m not pretending as though I’ve overcome this by any means. But the only thing that has really worked is setting myself straight on the only way to truly show remorse for the way in which I did something before is to do it differently next time.
And if I’m dragging myself down and holding myself back, I’m not going to be able to achieve that. I’m not going to be that better person that I had wished I was in the past. I can only be that person right now. And if I’m filling my mind with all this negativity about me, essentially, then how can I be that great person? It just doesn’t make sense. I have to be really positive about me. I have to be loving and caring and set the attention of doing great and being the best version of myself right now.
And if I’m holding onto that regret in the past, then how could I possibly do that? I just don’t think you could do both things at once.
Paul: Well, you’re right in that you’re not living in the present, right? Because we’ve talked a little about living in the future in the past, and - we talked about living in the future in the past. We’ve talked about that, and I think - I’m wondering if this is just - not just, but if this is a counterpart to that.
Is regret realized by living in the past? I’m wondering if that’s what it amounts to, because when I think about the examples that are there for me, they’re all in the past. I mean, there’s nothing that I regret that hasn’t happened yet. It tends to be a past-tense thing.
So, if I stay there, if I stay in that spot and relive it and essentially be there, then I’m denying where I am in the present, because I’m not there anymore. I’m not. I’m kind of replaying that in my head. And that’s a very different spot to be.
I’m wondering then also if - oh, gosh - if this is something that, again, varies by significance. I think it does because I think about the small things, thinking about the food, thinking about the little choices, thinking about wishing you’d done something sooner which, boy, that resonates with me.
I think about that with a lot of things. I think about getting my current job. I wish I had explored that sooner. But when I say that there’s a little wistfulness in my voice, and there is a little regret with that. But I also acknowledge that, hey, it didn’t happen sooner. And I also choose not to spend a lot of time thinking about what would have happened if I had done it sooner either, in part because the outcome has been really positive.
But I’m wondering if it really is just being in the past too much instead of being in the present, and as you say kind of realizing that if you spend time there, if you spend a lot of time there, not just for grins but if you choose to spend your present in the past, then how can you really be here now?
That becomes really hard to do because you may get into a feedback loop. You may become preoccupied with the past. And I guess it depends on the severity of things, I guess. But you’ve got to be here. I mean, that’s what it amounts to. And regret for me is - I think it is a manifestation of just this past stuff that is no longer there but it still exists in our heads.
Whitney: And if you aren’t here now, you’re probably going to have a lot more to regret later.
Paul: Yeah, it’s kind of a domino effect, isn’t it?
Whitney: I think so. I absolutely do. And maybe our regrets are ultimately about the times in our lives when we weren’t truly present, that we did things that don’t really coincide with who we are, our true nature, because we were distracted or we were spread too thin or we were stuck in the past or worried about the future and we weren’t really there. And so, we did things that were out of character because we weren’t present.
Paul: That’s really insightful. I like that idea a lot. And it kind of puts a neat little bow, right, because it ends up being then if that works, then - and I like this idea because then it’s pretty much, hey, if you’re not present, if you’re not articulating who you are in any given moment, well, isn’t that something that you may regret later?
Maybe it is if you allow it to do so. I’m kind of turning it on itself here. But I think about it, and you may be right with this. The times in my life and the big and small choices that I regret were, in part, due to me not being myself in that moment and just not acknowledging my whole self.
Maybe a part of me was really satisfied. Well, that’s the hard part. Maybe a part of me was really satisfied in that moment, but it wasn’t representative of me as a whole. And again, I don’t see that as inherently bad, but it is something that I notice.
Whitney: Absolutely. And I am immediately reminded of people that I have in my life whose parents, for instance, were always working. And they weren’t really around for important events in their childhood because the parent felt as though they had to provide or whatever they felt that was their purpose outside of being with the family.
And I hear it over and over again that these people, as they got older, regretted that they’d made the decisions that they had to be away, to not spend that time with the people who really mattered to them, the people who they really loved.
And I think what that’s about, ultimately, is a lack of being present for other people. They may have been present for the wrong people in their lives, like the person who was writing their checks. But they weren’t present for the people who really mattered to them. And maybe they weren’t even present for their own lives.
Had they taken a moment to reflect on the course of their lives or the priorities that they had, perhaps they would have chosen differently. But they didn’t take that time to reflect because they had a singular goal and everything in their life was designed to support that. And it was only when they retired, they got sick, they got fired, whatever, that they had this opening in their lives or this interruption where suddenly they looked around and they were like, whoa. Who was that person doing all those things?
Because those behaviors don’t really coincide with my set of values. And was that not me? Was that a different version of me? Have I grown since having done those things? Or was it just that I wasn’t evaluating what I was doing in those moments because I wasn’t really there. It was my body, but it wasn’t really my heart.
Paul: yeah, or it was a part of you but not all of you. And I’m really having a hard time with putting a value judgment on this stuff or not. If in a previous moment I chose to do something and now I regret it, the whole idea of being focused on a singular thing that is not necessarily representative of all of you, I get that and that resonates with me.
But isn’t that potentially just a part of us kind of being in the driver’s seat for that moment? Is that anything that’s inherently good or bad? Or is that simply what it was, potentially? One theory, blah-blah-blah.
Whitney: Well, I am drawn to this concept of birth and rebirth in Buddhism, that there’s this endless cycle of being reborn after death, that the intent is essentially that you get another chance and your energy is transferred into another being and based on your karma you either are a higher being or a lower being.
I’m grossly oversimplifying it, but I’ve been thinking about this a lot lately with the passing of some people in my life. And I wonder if there isn’t something really lovely about choosing to believe that we get another chance that in a way allows us to not place a judgment on regret and say it is what it is. It’s not bad or it’s not good. And in our next lifetime, we’re going to have a chance to do it better. So what’s the point of worrying too much about it in this lifetime?
Paul: Well, you have potentially the next lifetime, but you also have this one. I mean, you can also not worry about it now, right? I mean, that’s a choice now as well.
Paul: What do you think about bucket lists?
Whitney: Well, I have a lot of feelings about them. I’m thrilled that you're asking.
Paul: You’ve got the feels. That’s great.
Whitney: I do. I have never called it the bucket list because that’s just way too morbid for me. Like, kicking the bucket, not my thing. And maybe I’ve always - not maybe. Let’s be honest. I’ve always worried that I won’t make it as far along as I want to just because I’ve seen a lot of crazy shit in my life.
And I’m the opposite of most people who think they’re immune to all of it and think they’re immortal. Like, a lot of people that are young think they’re totally immortal and that could never happen to me. I have the opposite affliction where I’m always sure it could happen to me.
So, I haven’t really wanted to call it a bucket list because if I don’t get a chance to do it all before I kick the bucket, that’s going to be a regret. That’s a big regret for me, a future regret. Instead, I have a list of things I want to do. And back in the early days of the Web I had a 43 Things account. Do you remember 43 Things?
Paul: Yeah, absolutely. I had a 43 Things account, too.
Whitney: Is that Merlin Mann?
Paul: No. He did 43 Folders. You’re thinking of 43 Folders. Sorry.
Whitney: Well, who did 43 Things?
Paul: I don’t know. I bet the internet knows.
Whitney: I bet the internet knows. Anyway, it was, I don’t know, back in the day. I can’t even remember. And I’m going to say back in the day now thinking it was, like, ’95. But it was probably, like, 2005. I don’t know.
Paul: You’re exactly right. It was 2005.
Whitney: Oh my God.
Paul: That’s it, only 2005.
Whitney: Oh my God. Well, it feels like back in the day to me. But anyway, there was 43 Things and 43 Places. And they were two URLs, but they were similar concepts, same design. And one, 43 Things was the 43 things that you want to do in your life, bigger goals than, like, whatever, short-term work things or I want to get this promotion. Bigger stuff, big hopes, maybe. Hope, I think, is a good way of putting it or just - because goals sounds so dry.
Paul: Goals is such a business-y term, right?
Whitney: Yeah. Life desires, OK.
Paul: Sure. I like that.
Whitney: So, that was 43 Things. And then 43 Places were the 43 places that you wanted to go, that you really aspired to travel to. And I had accounts with both or had lists with both. And I’m not afraid to admit that I still read and maintain my lists on both sites.
Paul: Wow. That’s awesome. Holy smokes.
Whitney: And early into my relationship with Fredrick, we compared our lists of things that we wanted to achieve in life. I am purposefully not calling it a bucket list. And we looked the similarities and we put together a Google Doc. And we now have this list of each of our desires and then the things that overlap and that we really want to experience together.
I was about to say achieve together but I stopped myself because it’s not about achieving. It’s not a to-do list. It’s about experiencing, the life experiences that you desire to have. And it’s been really fun because when we’re planning a vacation or when an opportunity comes up in our lives to do something really different.
Periodically, we look back on that Google Doc just as a reminder for those things that we really aspire to experience in our lives, separately and together. And I’ve had a lot of very interesting things on my 43 Things list. Let’s see if I can pull it up quickly.
Paul: I actually pulled mine up while you were -
Whitney: You have an account, too?
Paul: I have an account, and it’s still there. And it’s marvelous because it’s so old. And I look at the photo and I’m like, wow. That was a long time ago. But I’m looking at this, and here’s what’s great. I’ve got 12 things still on my - I only have 12 things on my list because clearly I lost the plot and just didn’t care much anymore.
I finished three things out of my original 15. But the cool thing is that if I look at the list here, the current life list for me on 43 Things, there are things that I have actually accomplished since I last logged in, which makes me feel pretty great.
Whitney: Well, tell me some of your things, please.
Paul: Well, OK. So, learn CPR, did that. Redesign all my websites, I’m going to go ahead and qualify that I did do that because I ended up just not having websites anymore. That worked well. Buy a house, did that. Try yoga, did that. I’m really happy that that was there eight years ago.
Watch less television, yeah, that kind of happened anyway. Learn basic woodworking, yeah, mostly did that. Learn how to carry a tune, yeah, I totally have done that. Be a better cook, arguable. Clean out the closet, I sure hope I did that at some point.
Whitney: Wow. That was a lofty goal.
Paul: It sure was. Make movies, that’s pretty vague. I like that idea.
Whitney: I love that one.
Paul: I’m going to go to my favorite one last. I’m going to skip. Get out of debt, yeah, that would be lovely. That still hasn’t happened. But the one that’s on here, and I have no regrets about sharing this with anybody, is perfect a cookie recipe and sell cookies for a living. That is on my list.
Whitney: Oh my God, Paul.
Paul: That is on my list. And there was a time when I started really kind of working on that, actually, working on a recipe.
Whitney: Have you forgotten about it until this moment when you’re rereading it?
Paul: No. Here’s the thing. That’s something I’ve carried around with me that’s just kind of been with me. There have been times in my life when it’s been more of a, hey, that’s a great idea. And there have been plenty of times where it’s like, yeah, that might be cool to get around to someday. I don’t feel regretful about that, but I do carry that around in the back of my head and have for a long time. So, there you go.
Whitney: Wow. Oh my gosh. Well, I have to reciprocate now.
Paul: Yes, you do.
Whitney: OK. I have 26 things on my list that I have yet to achieve. And I have three or - no, I have how many that I’ve actually - one, two, three, four, five, six, seven that I have been able to check off the list.
Whitney: OK. So, from the top, see the Northern Lights, which is amazing to me that this is my number one dream because I’m now in a relationship with a Swede. And so, it’s significantly more likely now that I’m going to see the Northern Lights, given that you can see them from Sweden.
Participate in a protest, and as much of an activist as I consider myself to be, and very opinionated to boot, all throughout college I managed to not participate in a protest. And I really do regret that because I am never going to be back in college and I’m never going to be 20 again.
Paul: Well, here’s the thing. You Tweet about things, right? That’s pretty much -
Whitney: I Tweet about things.
Paul: That counts.
Whitney: Maybe. Well, there were a couple of protests on campus that I was, believe it or not, too busy to participate in because I had, like, tests and I didn’t want to bother. And I do regret that now because the tests mean nothing compared to the satisfaction that I would have gotten out of sharing my voice and fighting for something that I believed in. So, all right.
Number three, live in a loft. I’ll be shocked if I ever achieve that given what lofts go for these days. And next is buy an apartment, which I regret putting on the list because I’m not sure I want to own one anymore.
Get a dog, which I really want - I grew up with dogs and I miss having a dog. But my travel schedule just doesn’t allow for it right now. But we are getting one at some point in the future for sure.
Whitney: Here’s an interesting one that shows times have changed. Open an independent bookstore.
Paul: Wow. That was a long time ago, wasn’t it?
Whitney: Yeah, that was probably quite a long time ago.
Paul: How do you feel about that now?
Whitney: I feel still awesome about it. And maybe one day I’ll do it and I’ll be like those cool old dudes that have record stores with only vinyl, where it becomes like a hipster thing. And maybe I’ll bring books back or something.
Paul: There you go. Books are the next vinyl. There you go.
Whitney: They so are.
Paul: Oh my gosh.
Whitney: I am a book lover. I love a physical book. I had a ridonkulous collection of awesome books when I left New York and I ended up selling most of them back to The Strand, which is the coolest and best bookstore in New York City.
And I do not regret getting rid of them because it was a physical burden that I just couldn’t carry along with me. But maybe one day I’ll get to have a bookstore, independent bookstore.
OK, learn to cook, really cook. I’m now with a man who really knows how to cook, and I’ve learned quite a bit. But the pressure is off there. Self-publish a book of my dad’s photographs -
Paul: Oh, wow.
Whitney: My dad was a professional photographer for a while and is phenomenal and picked it back up in the last few years doing things digitally. And maybe I will get a chance to do that at some point because his work really should be seen.
Buy a Vespa. Go for a boat ride in Central Park. Despite growing up in New York, I’d never taken a rowboat out in the middle of Central Park. Here’s a weird one, and I don’t know that I’m going to go into it right now but I’ll put it out there. Buy a hedgehog.
Paul: Buy a hedgehog? Wow.
Whitney: I’ve always wanted a hedgehog. I’ll explain more another time. Hang-glide, which I totally see as being possible. And actually there’s places to hang-glide in Key West, so maybe I’ll go do that this weekend.
Paul: There you go. Nice.
Whitney: Live in Paris. Live in Sienna, which is my absolute favorite place on Earth in Italy. Write a book, which I do see as being a very plausible goal even though it’s going to be a lot of hard work, but that is in my future. Watch all movies on AFI’s 100 Best Movies list.
Paul: Oh boy, that’s a good one, too.
Whitney: I tried doing that, and I got halfway through. And then the other half I was like, I cannot watch these films. They’re just awful.
Paul: Wait. Which was awful? Do you remember specifically?
Whitney: I’m going to say it, and I’m going to get hate mail.
Paul: This is exactly why I’m asking.
Whitney: But I’m going to stand by it. West Side Story.
Paul: OK. I can see that.
Whitney: I love the music. I love the musical. I’ve seen the musical. The movie didn’t do it for me. Anyway, moving on, learn how to drive stick shift, which it would be a friggin’ miracle at this point if I ever learn because so many different people have tried to teach me, and Fredrick very early into our relationship selflessly offered his beloved Mazda Miata for me to learn on and ended up having to get a new transmission for it because I did not take to it well.
Have babies is on the list, and I regret putting that on there because I would love to but you never know. Am I really going to put that on a bucket list? Life turns out the way it turns out, so that’s not really something you can control.
Learn more about Judaism. Learn more about wine. Practice my French, which isn’t very measurable. I suppose I can practice my French any time. I don’t know how to check that one off. Exhibit my photographs - I do love taking photos, and that would be really fun. A near-impossible feat, stand on every single block in Manhattan.
Whitney: Where I came up with that one, I’m not quite sure. Stand atop the tallest building in the world, which I would love to do. I think that it’s in Dubai, is it not?
Paul: I believe that’s true. I could be wrong.
Whitney: Yeah, and it’s like 150 stories or something insane. But that would be really cool.
Paul: That would be cool.
Whitney: Ride a Zamboni, that’s a pretty awesome one. And then my last one that I know that I’ve added recently, at least in the last couple of years, is drive in Autocross.
Paul: Oh my gosh. That’s awesome.
Whitney: Those are mine.
Paul: Those are great. Now here’s the thing. 43 Things also has a tab - well, there’s the Done tab, which is great. I’ve done three things. And the first one, I’m going to fill you in on this. And we’re not just going to read lists for the rest of the show, although that might be kind of fun because we love lists.
The first one, though, is display my photos in a public place, which I did and was great and I highly recommend it. And then there’s -
Whitney: Oh my gosh.
Paul: And my second one, which I love, is learn ASP.NET. and then there’s a worth it/not worth it evaluation, and I put not worth it, which is absolutely true. It is not worth it. I highly recommend it.
Whitney: That’s awesome.
Paul: So here’s the other thing, though. There’s another tab. It’s the I’ve Given Up tab. Do you have this, too? I have it. I have my things, my resolutions. I’ve done three things. And there’s an I’ve Given Up tab.
Whitney: I have the most awesome one item in my - master Flash.
Paul: Master Flash? That’s marvelous. Oh my gosh.
Whitney: Master Flash.
Paul: Wow. Well, you figure this is - when did you join, 2005? Is that right?
Whitney: It must have been.
Paul: And that was when Flash was still - I’m sorry, go ahead.
Whitney: Yeah, member since 2005 it says in here.
Paul: Nice. I have that as well, 2005. So, yeah, apparently Flash - I remember Flash was still relevant in 2005. That’s an awesome skill. So here’s the thing. My I’ve Given Up is improve my guitar skills. And I regret putting that in I’ve given up because I actually have done that now, which is really kind of crazy to think about.
The thing that’s fun about this is that these are time capsules. I totally forgot about 43 Things. I mean, I might have had it pop in here or there and be like, oh yeah, that was a great site. But then I didn’t remember my login, but then I did and got in OK using password1, my password I’ve been using since 1998 on every account ever.
And all this stuff is still there, and it’s really - how great is that, in a way? Like, we have this stuff here, but I look at this and I don’t have this tinge of regret. I don’t have this tinge of wow, gosh, this would have been great if I did all this stuff. I mean, yeah, there’s stuff that I haven’t done yet. But it’s cool.
I mean, I don’t see it quite as a bucket list, but I guess it is kind of one, I guess. But then if I get to a point where - like, make movies. That’s so broad, right? That’s on my list. That’s so broad. So, technically I’ve done that. I’ve done videos on the Web which I probably couldn’t conceive of in that same way in 2005.
So, I don’t know. I mean, that’s not something you just necessarily check off when you’re done. So, why do we have bucket list? Why do we have these things? And then why do we - because I’m wondering if it is a matter of, hey, I want a great list of stuff that I need to do or want to do during my life so I then can look back when I am retired or somehow I know that I’m going to die which we don’t all have the luxury of and look at this list and say, yeah, I did all that stuff. That was awesome. Is that something we need at that time? Maybe it is. I don’t know.
Whitney: I’ve never really thought about it this way before, but I find the whole making the list thing a little disturbing now. I mean, yes, it was super-fun to read back through these and hear yours and to be reminded of a time when these were the things that were truly important for me to achieve in my life.
But we’re evolving. We’re different people now than we were then. And what’s the point of having a list to keep track of all the things that you want to experience in your life that you make at a single point in time that you now feel obligated later in life to start to check off? I mean, how about do whatever you feel most drawn to do in the present moment? Is that not good enough?
Paul: That seems good enough to me. And again it’s one of those things that sounds so simple when you say it. But it can be harder to do. But you know what? I’m going to go back on that. I regret saying that. It’s not harder to do. It’s not hard to do.
If you are focused on the past or the future, well, first of all, recognize that if you can. Where are you now? There was this - ah, here we go. There was a wonderful Pastry Box article by Leslie Jensen-Inman that I will happily link up. Pastry Box continues to be awesome.
But she wrote about how when she is not really present what she does is she will remind herself to look at where her feet are and remember where they are.
Whitney: I love that piece.
Paul: It’s so wonderful. It’s so good. And I’ve actually found that to be very useful for me, too, because otherwise I’m not really in the past. I’m not really in the future. And it feels like with this, with dealing with regret and dealing with these things that we may see as mistakes that we may need or want to atone for or forgive ourselves for - the forgiveness of ourselves is very important.
But there’s also, again, another component here where you’ve got to be present. You can choose not to be, yes, but then your consequences are going to be a lot different and you’re not really here. So, it almost feels like almost everything we’ve talked about comes down to presence.
Whitney: Every topic - I mean, this is episode 10, and every topic that we’ve had so far has ultimately been about presence.
Paul: How does that happen?
Whitney: Because presence is everything. I mean, it’s the greatest gift that we give ourselves. It’s the greatest gift that we give the people in our lives. And I really, in a way, regret even looking through this list of 43 things because I feel as though this list is causing me to look back on all of the things that I still haven’t done in my life and that I once wanted to do, that I once wanted my life to be about.
I wanted my life to be the sum of these experiences. That’s why I put them on this list. And even though that was me at, if I do the math quickly, 23 and now I’m 31 and who I am at 31 is very different than who I was at 23, I am feeling this little bit of, oh wow, look at how few of these things I’ve really experienced in my life.
And I’m starting to feel that little pang of regret. But meanwhile, I’ve been living my friggin’ life. And I’ve done so many things that I never imagined I would do. Like, you know what’s not on this list? Speak in front of an audience.
Paul: Oh. Holy smokes. Yeah, you’ve done a little of that.
Whitney: And I’m going to tell you, every single time still feels like the first time. And it’s shocking. And that was a huge life accomplishment for me because I went through high school never being on a stage. I went through college never being on a stage. I mean, short of receiving my diploma at graduation, I had no experience with this. And it was a major fear for me.
So, ever speaking in front of an audience in the first place was a huge life accomplishment. The reason it wasn’t on my list in the first place was because I didn’t even think I was capable of it. I didn’t even know it was something that I wanted to do. It wasn’t something that I wanted to do. It was something that happened because life put me in that position. I got the right encouragement from the right people at the right time.
It was beyond anything that I’d ever expected of my life, and it turned out to be one of the most rewarding experiences. And it is every time that I do it. So, you know what? I don’t think I’m going to look at this list again.
Paul: All right. Fair enough.
Whitney: Now that I’ve said that I regret saying it because I’m probably going to look at it a bunch more times.
Paul: You said never. You said never, and never is never, never again.
Whitney: Never say never.
Whitney: But I think I will look at it with as infrequent - minimal frequency as I have already because I can’t recall the last time I looked at it. I think it’s nice, as you say, as a time capsule. But I don’t think it has any relevance on the person that I am today.
And if on my last day I were to look back at this list and see that I didn’t achieve these things, the best thing that I’ll be able to feel is pride for the person that I became and all the other aspirations that I had, and that I wasn’t simply living the life that I had imagined at the age of 23, that I allowed it to evolve naturally and that I went with it.
Paul: I mean, that sounds totally reasonable to me. I am tempted to go through this list myself, my own list, and just kind of check off all these things because there’s a part of me that really is just like, yep, did it, yep, did it, yep, yep, yep. But there’s something really profound on this page as well.
Since we’re on the topic of 43 Things still, the text box that you fill in and add an item, the label on it is very simple. It’s “What do you want to do with your life?” And the button is “Add” and that is it. That is all it is.
And there’s something really beautiful about that. But then, much to your point, why the hell would you put that in a box on a website? Not diminishing the entire idea that we just talked about, because it’s certainly fun, and I love lists. But I wouldn’t want this to - I would not really want this to be something that is pretty much a tally ort a scorecard or anything like that because it doesn’t really change with me.
And maybe that’s just because I haven’t updated it. But then that would be a lot of updating because it could change moment to moment, you know?
Whitney: Right. You know, it’s funny. The instructional copy on the text box reminds me of the early days of Twitter where the message was, “What are you doing?”
Whitney: And so, a lot of Tweets in the early days were verbs, really. They started with verbs - writing a blog post or going to the supermarket. They were almost like a play-by-play about your life. And then I remember at some point in the many, many iterations of Twitter over the years that opening question was removed entirely, or it was just changed to Tweet or something. I don’t know that it was nothing, but I’m pretty sure that it was.
And I didn’t remember what it was now because I either use Tweetbot on my iPhone, which is where I’m using Twitter 99% of the time, or I have the desktop Twitter for Mac, I guess it’s called, that when you compose a new Tweet doesn’t have any message at all. But on the Twitter website when you compose a new Tweet, now the copy is, “What's happening?”
Paul: Oh, is it? Because I’m looking at it now and it says just “Compose new Tweet” for me. That’s it.
Whitney: And then click on it.
Paul: Yeah, still nothing, just “Compose new Tweet.” Maybe they’re A/B testing.
Whitney: You don’t see what's happening?
Whitney: Oh my gosh. You mean, in the popup window itself, that layer, you don’t see “What's happening?”
Whitney: Dude, we just uncovered A/B testing in the wild. Oh my God.
Paul: Yes. Finally.
Whitney: We’ve now screwed up all of their testing. It’s now completely invalid.
Paul: Awesome. We’ve ruined testing for Twitter. It’s “Compose new Tweet” on my end, and it’s got an ellipses at the end and that’s it.
Paul: That’s it. That’s all it is.
Whitney: Mine says, “What's happening?”
Paul: Yeah. This is on the website, right?
Whitney: Yes. I’m not referring to the inline text box underneath your mini-profile. I’m talking about that blue button in the top-right corner of the screen.
Paul: Oh, I see. I don’t use that. If I’m using the website I use the “Compose new Tweet” that’s in the left sidebar because that is right there. I never use the thing in the upper right ever.
Whitney: I never use the website.
Paul: Well, yeah. I use it occasionally.
Whitney: I just went there to see.
Paul: That’s pretty crazy.
Whitney: But it’s interesting the difference in “What are you doing?” versus “What's happening?” and a list where you say, “What do you want to do with your life?” I mean, what I want to do with my life is stand on every corner in Manhattan? Why the hell is that how I wanted to spend my life? That doesn’t make a lot of sense.
Paul: But it doesn’t make sense to you now, but it surely did at some point. What’s wrong with that?
Whitney: I think quite frankly at the age of 23 I had no idea what I wanted to do with my life, so spending it standing on every corner in Manhattan sounded like a good enough idea.
Paul: Yeah. That’s fair. But at 23 almost nobody - here’s the thing. This is a big blanket statement. At 23 nobody really knows what they want to do with their lives. But they feel they’ve got a lock on it. That just goes with it. That goes with the territory. That’s how it - I think that’s fairly common on our society, and that’s how a lot of people in their early 20s, like post-college and life is starting to get together.
But at 23, for whatever reason, you wrote that stuff down. And that was for you - I don’t know what it was for you. Maybe it was fun. Maybe it was a lofty goal. I don’t know. But that was something that really resonated with you at the time. So, that’s cool. I’m just curious about the judgment on that.
I mean, I agree with you. My list, not so bad. But a lot of it is - it doesn’t represent me anymore for the most part. I suppose there are some thing that have definitely changed. There are a lot of things that are absent here. But it doesn’t reflect me now at all. But I also recognize that, hey, eight years ago, 8.5 years ago when I made this list, that was what - that’s me. That’s a piece of me from 8.5 years ago. That’s cool.
I recognize that it’s not me now. But there are things here that definitely carried over, like the cookie stuff. Yeah, I kind of miss making cookies, things like that. That’s been out of the picture. But then I look at things like “try yoga,” and that’s something that’s clearly been in my head for a very long time.
And I got it out at that point and I’m proud to look back. And if I could talk with the me from 8.5 years ago I’d be like, hey, you got around to it and you liked it a lot and it works pretty well for you, you know?
So I don’t see that as a bad thing, and I don’t pass - for my stuff I’m not saying this is a bad thing. It simply was who I was at that time, that’s all.
Whitney: Well, you do realize, Paul, that you are now required to bake me cookies.
Paul: Crap. OK. I can do that. But I have to perfect the recipe. That’s what I have to do first.
Whitney: No. I assure you I will like them just how they come.
Paul: I can do that. I can do that.
Whitney: So, I mean, I think that this foray into our past selves was very appropriate for our topic. And I appreciate you bringing up the bucket list because it goes to show that feeling remorse over your past self is really a giant waste of time. In fact, you should be proud. You should be so proud that who you are now isn’t who you were then.
And it’s just as great that there are some threads that have carried through over time, like yoga, like cookies. It’s thrilling that those parts of who you were then have remained. But there are so many other parts that have changed, and I still would love to publish a book of my dad’s photos because I consider him to be wildly talented and I feel that his work deserves to be seen.
But standing on every block in Manhattan seems like a giant waste of time, and I have a much greater purpose in my life now. So, regretting who I was then or having not done the things that I set out to do with my life, you know what? That’s good. That’s a really good thing because it means that I’ve grown. I’ve developed. I’ve had new aspirations and new ways of spending my time.
And I just have to trust, because I really don’t have any other choice, that I have made the right decisions for myself at the moment that I had the decision to make. And even if my future self looks back and thinks that was a bad idea or I wish I’d done it differently, I’m still doing what’s right for me right now. That’s the absolute only thing that I have is making sure that the decisions that I make with my life, the way that I spend my time, how I treat myself and how I treat others, is precisely what I want it to be right now.
Paul: Brilliant. Absolutely brilliant.
Whitney: Well, I don’t think it’s brilliant. I think you think the same thing.
Paul: I do. Well, that’s why I think it’s brilliant, because I think the same thing. Come on. No, I agree. I agree. And again it comes back to presence and who we are now. That’s huge. That’s what it’s all about.
Whitney: That’s all we have.
Paul: That’s it. That is all we have, for sure.
Whitney: Well, I am so grateful to Ryan for giving us this topic today. And I’m glad that we were able to squeeze so much out of it. It really is very rich.
Paul: I agree. This is - what a wonderful topic. Thanks, Ryan. And, as Whitney said at the top of the show, if you have a topic idea, please let us know. Whitney, how can people get in touch with us?
Whitney: Oh my goodness. There are so many ways. Firstly, you can Tweet at designingyou, which is the short version of this show name, Designing Yourself, but that’s too many characters for Twitter. So, at designingyou. You can Tweet at PaulMcAleer or at WhitneyHess with a show idea.
You can, of course, send an email to our super-secret email that only really special people use, but you of course are a special person, too.
Paul: Yes, you are.
Whitney: And that is firstname.lastname@example.org. You can - I don’t know. What else?
Paul: Well, I think people can look us up on 43 Things. There’s stuff there.
Whitney: Yeah, you can comment there. You can send us a fax.
Paul: Yeah. The fax lines are open. We have the hotline ready to go, so if you want to fax over your show idea or whatever else you want to send over that’s fine with us, too.
Whitney: Yeah. I suppose if you have our cell phone numbers you can call us or send us a text message or something. But try the other methods first. And I think you will find that we are quick to respond.
Paul: We are, because we love the Twitter and we love feedback as well. And then your feedback is really valuable in general. I mean, for goodness sake, whenever I see our show mentioned on Twitter, I get a little flutter, get a little twitterpated, pun fully intended. That was a pun, by the way.
But, you know, it’s lovely to see, and the feedback is always welcomed, good or bad or neutral. So, please keep it coming. And as always, Whitney, thank you so much for tonight’s conversation. This has been wonderful.
Whitney: Thank you, Paul, for 10 beautiful episodes so far.
Paul: Yeah, 10 episodes. So great. So glad we’re doing this.
Whitney: So, we’ll be back next week with another very small and easy-to-define topic.
Paul: Absolutely. Have a great week, everyone. Take care.