Rob and Sherry talk about dealing with transitions. Pulling from their own current life transition they put together five strategies that can help people cope during the tough times that can arise.
| Rob Walling: | This week we are talking about dealing with transitions and we are experts in this recently, having dealt with recent cross-country move for the four of us. Both of our kids changed schools, obviously as well as homes and then city locations. I have essentially transitioned jobs and you’ve done all that plus essentially left a full-time job in Fresno to basically be doing a very part-time thing right now and kind of try to figure out what your next act is. |
| Sherry Walling: | Yeah, I know big changes and all. |
| Rob Walling: | It’s a lot of impact into 60 days or 90 days or whatever. I guess it’s actually a little bit longer than that because we had the house on the market and then it sold and then we moved out of it. Then we moved in with friends and then we lived in Oregon for a week and at the beach for two or three weeks. There’s been a lot of transitions over the past few months. |
| Sherry Walling: | I think this timely my topic not only for us, but for people who have children in school. Lots of families are doing transitions now as they shift from kind of a more city schools. Some are scheduled to a more structured school schedule and I think that people are always going through different kinds of transitions, especially in the life of a founder where your work might have lots of different iterations and certainly people who have families are often going through the ebbing flow of change. |
| We are not trying to just talk about our situation and our life changes, although it’s so front and center in our lives. We can sort of hardly talk about anything else, but obviously the goal is also to make it applicable to the different kinds of transitions that other folks are going through. | |
| Rob Walling: | Right, because if you are a typical founder you’re going to be going through a number of transitions every few years probably. You’re likely to perhaps relocate, perhaps move from home to home. Almost certainly if you are a restless founder, you’re going to be changing jobs and/or leaving your job to move to consulting or to move to products, completely anecdotally. The founders I know they are just reinventing themselves pretty frequently. We tend to get restless and it’s both a blessing and a curse. |
| The blessing is that it keeps us moving forward; it keeps us growing, keeps us learning and makes us interesting people. Then the curse is that sometimes you get restless when maybe you should stay and focus and you’re introduced to transitions that maybe are detrimental or maybe there is too much transition. The idea is that founders in general, I think are going to go through a lot more transitions during their lifetime than someone who takes that 9:00 to 5:00 job and works for 20 or 30 years. | |
| Sherry Walling: | I think that is very true, also anecdotally. I think that’s part of the founder personality because the founder itches to have more freedom and control and that freedom and control creates for most folks a certain degree of flexibility. People are moving to different places, people are nomads for a while or are shifting even within the kind of business that they are running as they are trying to pivot, to use my good Silicon Valley language and keep up with the different changes in technology as everything moves quickly. I think transition is a really important thing for founders and their families to have a pretty strong grasp on how to do transition well and not let it sort of steam you and derail you. |
| Rob Walling: | Yeah because transitions in general are hard even for people who are good at transitions. They often don’t know what to expect. They don’t fully grasp the challenges that it’s going to create. Recently with our move here to Minneapolis, I thought the transition, the move transition would be really hard and I was not looking forward to it and I was very stressed out about it. I think you were a lot more comfortable with the move, but I think you were a little bit blindsided by how hard it was to leave your job. |
| You’ve talked about that a little on the podcast that leaving that identity behind and leaving some of these clients you’ve seen for a long time, leaving your coworkers. I mean the whole thing was … It was a transition that the difficulty of it, the extent of the difficulty kind of came out of nowhere for you. | |
| Sherry Walling: | The difficulty in the transition for me wasn’t the location as much as some of the identity shifts that happened for me as we made this move. I think that’s a really important thing to continue to hit home over and over. We’ve said it before in the podcast, even in recent episodes, that even really good changes can be really hard. In fact, some of the best things that happen in people’s lives, having a baby or getting married or getting a promotion or taking that new job or selling your company. |
| They are really positive, good things that are desirable, but they come with some emotional angst like a significant amount of upheavals to whatever patterns were existing in your life. I was really happy and excited to move, but the sort of who am I and what do I do with myself all day parts of it were much more difficult than I expected. | |
| Rob Walling: | If you could have relocated to the new house, isn’t a big change for you or it is a change, but you go really well with those kinds of changes. The new city is also easy, but it was that job and it’s like if you could have transported your old job here with all your people, it would have been so much simpler. |
| Sherry Walling: | Absolutely. If I could just bring my people with me, that would be great. |
| Rob Walling: | Which is … There is something to be said for that. We have put together five tactics or five steps to dealing with transition and it’s things that we are kind of pulling out of our own experience, it’s both you and I. It’s also the experience of our kids who have experienced a lot of transition in terms of their, like I said new house impacts them a lot. It impacts us a lot less. I think you and I have lived in a bunch of different houses during our lifetime. Our youngest, he had never lived in any other home aside from the home in Fresno. |
| Our oldest really didn’t remember the home before Fresno. To them, this is a big deal. It’s a big deal to leave that and then the city being different is another one although for them, probably smaller. For us, the city being different is I think pretty impactful because we have to learn to navigate it and we have to find just all the stuff, the dentist and the doctors and the repair shop and the place you get your hair cut and all that stuff, whereas the kids don’t have to worry about that. | |
| I think it’s more of a transition and then for them schools, not being around their friends and not being oriented at the schools. There’s a lot of transition for the whole family and we’ve noticed each of us deals with them differently and each of us gets hang up on some things and it’s a lot easier for some of us to deal with other things. | |
| Sherry Walling: | How do you think you’re dealing with the transition? What are your coping strategies or? |
| Rob Walling: | That’s a really good question. I think my coping strategies have been … There are a couple of things. It’s to find a familiar because I like the familiar a little more. I’m thinking I started kind of listening to podcasts again and it’s very specific podcasts that I’ve listen to for a long time. On my drive into work or on my ride in, pop the ear bud in and I can here Tom Merritt’s on Daily Tech New Show. I’ve listened to him for … I don’t know, four, five years. There’s just a lot of podcasts that I’ve listened to and it’s comforting. I’ve also started going back … I haven’t been listening to music a lot, except for when I’m really kind of deep in the trends, deep in the trends of working is what I mean. |
| When do you do this and turn on the [inaudible 7:37]? No, I’ve been outside of work. I’ve been listening to music quite a bit but it’s all older music. It’s music from … I don’t know, within the past, let’s say 10 to 20 years, just kind of stuff that I’m rediscovering and that feels familiar. It institutes or insights a feeling of maybe more familiar or some comfort. Then I think you and I hanging out and even with the kids like going out and doing adventuring things like we played golf on the roof of the Walker Museum here, the Modern Art Museum. We’ve been out on the paddle boats. That helps because it’s so much fun. I think that’s been another one. | |
| I then I realized that really early on when we moved in here, one of the first things I wanted to get unpacked and put together was the kitchen because cooking for me is part of that, it’s part of feeling. For me feeling at home is having the ability to know where everything is in the kitchen and being able to navigate it, make some dinner and do that. I think those have been my coping mechanisms. How about you? | |
| Sherry Walling: | It’s funny I feel like I almost have the opposite strategy. If yours is find the familiar and develop or return to former patterns that felt comforting and familiar to you, mine is almost like lavish in a novel. I’ve been doing lots of adventuring and making lots of plans to go places and try different restaurants and I have my checklists and my these things and my that things. For me I think my way of sort of coping with the discomfort is to like just rush headlong into all that’s new and different and really do everything I can to like enjoy and know and familiarize myself with the new environment and sort of take all of the good things that are available. |
| Rob Walling: | This is in line with our personalities, really much in line. Didn’t you take some test and it was like you were like an 11 out of 10 in terms of needing new experience? |
| Sherry Walling: | Yeah. Based on the big five model of personality, I think it’s a 16PF. Anyway, I took a personality test and most people are sort of in the middle-ish, maybe kicked to one side or another on the different aspects of personality. If personality is a spectrum, very few of us are like true hardcore all the way over to one end extroverts or introverts. One of the aspects of this personality scale is called openness to new experience. I’m like at the extreme edge of that, which means I have just a high degree of need for new and novel experiences. |
| Rob Walling: | Did that come with an asterisk that said like a footnote, “You will never live in the same place for very long. Don’t plan on getting married. Don’t plan on doing anything for more than a year?” |
| Sherry Walling: | That is not nice. |
| Rob Walling: | No. I’m just kidding. |
| Sherry Walling: | It is not antithetical to commitment, just so you know. |
| Rob Walling: | That’s good news. |
| Sherry Walling: | Yeah, I can rest easy on that. You go for familiar, I go for novel and I think our kids kind of line up in that way a little bit too. Our youngest definitely looks for patterns and longs for the old and is stressed out by new thing. Our older son actually really seems to relish in the newness of new experiences. |
| Rob Walling: | Both of them have enjoyed having their audio books playing for the past few weeks, which I think for them is a little bit of a comfort. |
| Sherry Walling: | They have been funny in their ways of developing their own patterns here. They come home from school and sort of have a snack and then run upstairs and instantly start making like art projects. They’ve created this whole like paper army of different characters and creatures that are like loosely based on books or video games and they just sort of mix-matched it all together. They’re creating like hundreds of paper creatures while they listen to audio books and they just sit in the quiet and color and cut and make these creatures. |
| Rob Walling: | It’s really interesting, for hours. It’s a trip and this isn’t something they did before we left. |
| Sherry Walling: | It’s a new thing here. |
| Rob Walling: | Shall we dive into these five steps for dealing with transition? |
| Sherry Walling: | Yeah. I think the truth about these five steps that I’ve written down in our outline is not so much that they are steps that happen in order or that they are tactics, but these are things that I actually have found myself telling myself and the kids. The first one is yes, this is hard. I really want to affirm for people in the midst of transition that it is hard. Whatever disorientation or upheaval you feel, whatever depression or anxiety you feel is completely in line with what it feels like to be in the midst of transition. |
| I want to say that to the kids because I want to acknowledge that what they are doing is formidable. I want to say that to myself because it allows me to be a little bit more gracious with myself when I’m having a bad day or I’m feeling like lonely or stressed or sad. I think the first thing to sort of acknowledge about any kind of transition again even if it’s like a positive change in your life, this is hard. Cut yourself some slack and acknowledge that what you are doing is a formidable challenge. | |
| Rob Walling: | I think hand-in-hand with this is that just because it’s hard it doesn’t mean it’s not worth it or it doesn’t mean you made the wrong choice. Even if it’s hard for weeks or potentially months, that if you made the choice when it made sense to do it, then kind of the negative emotional ramifications of it now shouldn’t necessarily make you rethink or doubt or regret that decision. |
| Sherry Walling: | Nothing that’s worth doing is easy. It’s a little bit of a saying, just a stitch on a pillow, but I think that’s really true. Anything that’s really valuable in your life is hard. It takes some guts and it takes some energy and patience and some real inner strength to do some of these transitions well. I think the second thing that I found myself saying out loud a lot to the kids especially as they’ve begun new schools in community schools that are really well established communities. We live in a neighborhood where people have lived here for lots and lots of years and there is not a ton of transition in and out of the neighborhood. |
| They are entering classrooms where the kids all know each other and the moms all know each other and the dads all know each other from last year’s potluck and preschool and all those other things. It’s not been simple to try to break in especially for our fifth grader because he’s kind of an odd kid anyway and now he’s the new kid and it’s really hard. I keep saying to him, “You’re so brave. You are so brave. You’re just … You just show up and you keep trying and you talk to a new kid every day and you keep at it until something breaks loose and you have a friend who wants to hang out after school. | |
| You just acknowledge the difficulty of this transition means that it takes a lot of hearts and courage to do this.” I don’t think we … We think of courage as like grand heroics, but I think there is a lot of courage that goes into little life things. It takes a lot of courage to decide that you are no longer going to work for yourself and run your own company, but you’re going to allow yourself to get sort of subsumed into a larger company where you have other people to answer to. That takes courage to just say, “I don’t know exactly what this is going to be like. It’s unknown, but I’m going to try it.” | |
| Rob Walling: | I think just as our first step here yes this is hard, gives you permission to feel things and to kind of admit to yourself that it is hard and it should be hard. This one I think, you’re so brave, is indicating that you’re strong enough to deal with it and that you’re going to make it through and that you have the ability and the power inside of you to overcome difficult things like these transitions, whatever transitions you are going through. |
| Sherry Walling: | I think that positive affirmation to yourself is really important. This is hard, but I have the resources to do it. It’s not always going to feel good, but I’m strong enough. The third thing that we’ve touched on a little bit, but the third thing that we have been working on with our kids, I sort of call transitional objects. I think what you said earlier about find the familiar is the adult version of that and we talk about transitional objects in psychology or often we are talking about child development and children making a leap from one development to like task to another developmental task. |
| Sometimes there is this thing that helps them get through. The classic example is sort of the blankie that you take to a daycare because it’s your first day being away from mom and dad and so you take something familiar and comforting with you to this new environment. When you put the kitchen together and you’re like, “Now I know where the spatula is.” that’s your transitional object in that moment, it feels familiar and comforting. | |
| Rob Walling: | Totally. There is that one frying pan that has this coat that’s like German and it’s made of stone, it’s not Teflon and once I had that in my hand, I know how that pot feels in my hand. I know exactly how heavy it is. I know how the handle is shaped and then I have one spatula that is used to make eggs every morning. It’s just as lame as it sounds like the day that I started using those again and making scrambled eggs or whatever, it felt familiar and it felt more like oh okay, this is our new home. |
| This is what life looks like now and it definitely helped me just feel more comfortable. It’s a little thing, right? It sounds like a little thing but I mean even with our youngest, he has been stressing out about school. First it was not wanting to go at all and then when he would go, he’d get a stomach ache right before lunch and he said it was because he missed us so bad and it kind of breaks your heart when you come home and be really sad about it. We came up with the idea of basically giving him literally, it was like a card that had come in the mail on some junk mail and I don’t even remember what the card said but it was just a little … it was like the size of a business card, but it was a little fancier and it was a thicker card. | |
| I said “This is your mom and dad card. Take this with you and it will remind you of us.” I mean I just kind of made it up on the spot and he took it the next day and he did better. He didn’t have the stomach ache. I don’t know how much it particularly helped him, but he didn’t have the stomach ache and then he said “I lost the card and got really upset.” Then I just gave him each one of our business cards and basically said the same thing and it’s nice because the business cards are basically expendable. | |
| Even if he loses them, we are okay. I think that that’s the type of maybe transitional object that he needs at this point, being six years old. It’s just something to remind him that we are out there and that maybe when he’s thinking of us, we are thinking of him or whatever. | |
| Sherry Walling: | There’s something really funny about that though, our little kid carrying around our business cards. |
| Rob Walling: | I know it is. |
| Sherry Walling: | We couldn’t give him like a photo or. |
| Rob Walling: | I couldn’t find … I was thinking like what can I give him, but we don’t … I just didn’t have any photos. I guess with that Kodak instant camera we can do it, but … or I guess we can print them out. Anyways I didn’t think of it at the time. I think he was like ready to go out the door and so I grabbed … it was like the mail was there and I just grabbed the thing and now we are using cards. |
| Sherry Walling: | He keeps it in his pocket and it’s really. Finding these familiar patterns or certain objects that bring a lot of comfort is a great strategy for dealing with transition. Then the fourth one is my strategy, that’s let’s make it fun like let’s just jump in to all that’s good and new about this new situation. I kind of talked about that already. |
| Rob Walling: | We didn’t dive into like the level of fun that we’ve had in the past six weeks. I mean seriously we’ve probably gone out to eat more in the past six weeks at a new place every time, than we have in the past … I don’t know, four, five months. I’m trying not to exaggerate, but I mean we literally are having these amazing brunches because Minneapolis knows how to do food. Their food selection is amazing. Then these brunches, we’ve gone and seen … Have we seen two live musical acts or three? Then we saw explosions in the sky the other night at 1st Avenue, it was iconic. Minneapolis Club for our kids. Like I said, we took them to mini golf on top of the museum. We’ve been to the … another museum several times, paddle boarding every other day. |
| Sherry Walling: | The children’s theater. |
| Rob Walling: | Yeah. |
| Sherry Walling: | Scooter rides, bike rides, live music outside, several playgrounds. |
| Rob Walling: | Just a lot of stuff. That I think your superpower is getting to a new place and figuring out what is cool and then basically executing and bringing the momentum. That’s a skill and you do it very well. We all want to go and especially once we get there, we have a lot of fun, but it takes someone to initiate it and that’s something that … you don’t have cataloged things in a Google Doc and so it’s always there. Then you’re the one that’s like, “Tonight let’s just meet at this happy hour and then take the kids to the waterfall.” |
| Sherry Walling: | It does take a lot of energy to like bring that active energy to a transition when you are already tired. It’s life-giving for me, which is why it works, but I understand why it’s not easy to have that strategy. |
| Rob Walling: | What the kids say, what their motto is, “Mom gets fun done.” |
| Sherry Walling: | The last strategy that we’ve been using or talking about as a family is phone a friend. This is just what it sounds like. It’s reaching out for help and support. I spent an hour on the phone with a girlfriend in Fresno the other day and it was just really helpful. I have scheduled different phone days with different friends. I have one friend that I talk to on the phone every Sunday night anyway. I’m just really spending more time on the phone than I have recently, but it’s been important to connect. Just again bridge that transition from people that I have known and loved for a long time to this new place with new people. |
| We’ve helped our kids do that too. They have … We have a family that we are really close to in Fresno and they have two daughters who are roughly the same ages as our boys. They’ve been doing sort of a loose once a week Skype date and just seeing that familiar friend and swapping stories about the new school year has been really important for them. | |
| Rob Walling: | I haven’t done as much of this remotely. I have been emailing with an old friend. It’s been nice but it has been good to have you guys here at the family because you guys are obviously good friends and then to have the rest of the directing team has been big, to be able to have Derrick and Anna and Zach and be able to go and hang out with them or to be at work day-to-day. I think that’s been … It’s been good to not feel alone. |
| I think if we had moved here and I was working alone in the office, which I did for a couple of weeks early on, it was pretty isolating and it’s pretty lonely to be the new person at a big company. I think if that had been the whole year, it would have been a lot harder for me for sure. | |
| Sherry Walling: | I think to wrap it up, whatever version of transition you’re going through in your life, appreciate that transition is difficult and it’s hard. Emotionally, it’s hard. Relationally, it can be hard on your body. There’s lots of level of hard. The fact that you’re doing it and that you are in the midst of trying to figure it out, I think means that you are so brave. That you are finding the strength that you need to work through the challenges and reinventing yourself in whatever capacity you’re doing that. |
| I think as Rob and I’ve talked about, there is this balance between enjoying the familiar, finding the familiar, surrounding yourself with comfort objects and comfort patterns and your special frying pan and the balancing that with jumping in to the new and exploring and experiencing the fun and the benefits of the new situation. Lastly, I think transitions because they are hard and they are a vulnerable time, they can really stretch you and if you are doing a location transition, it can be really lonely. It’s a great time to really reach out and connect to other people. | |
| Even if you’re not feeling very social or feeling very good, it’ a good time just to get on the phone or text back and forth with a buddy and just really connect with people who have known you for a long time, have a sense of your history and care about you and can show up and make you laugh or offer some encouragement. | |
| Rob Walling: | The thing I try to remember during these transitional periods is that any state you are in always feels like you are going to be there forever. I remember when our oldest was really young, a little baby and you’re dealing with frustrations and whatever, just splitting up too much or you had something wrong with this road and you split too much. Someone said like “That is going to go away.” like it’s going to be like this for three months or six months. |
| It feels like it’s going to be like this forever, but it’s going to change and that’s how I feel and that’s what I’ve been trying to think about, this transition because right now it is still a lot of logistics. It’s like we don’t have people who do things. We don’t have our … like I said, our doctor or the person … I went and got a haircut and I didn’t like the haircut and these are little things, but they are. They do just add up and they are micro frustrations and I keep telling myself like, “Yeah, but this all will be solved in the next few months.” It is a temporary state. |
Sherry and Rob open up about some of the events that have happened with their family in the last couple months. They talk about...
In this episode Sherry interviews Andrew Amann, CEO of NineTwoThree Digital Ventures, an agency that builds apps for mobile and web. Whats interesting about...
At the halfway point of the Founder Origin Stories series, Sherry and Rob take a break to give you their mid-summer updates on whats...