The following is a transcription of Voice of Bold Business Radio Program 59: The Flip Side of Procrastination

Program Notes Can be Found Here.

Transcript of Program 59 – The Flip Side of Procrastination

Jessica: This is The Voice of Bold Business Radio, and I am your host Jessica Dewell of Red Direction. You are listening to The Flip Side of Procrastination. Today, I am talking with Jason Michael, who is the head of support at RiteKit and is recognized social media engagement expert as wel as a developer of support teams and support processes for startups.

Make sure you subscribe to The Voice of Bold Business Radio, so you can hear Jason and our other guests and panelists, as we air shows every Tuesday and Friday.

What you’re going to find in the show is really interesting, because when I put it together, The Flipside of Procrastination… I wanted to talk about all the benefits of procrastination. Well… best laid plans… in the preparation, in the organization, something else started to bloom and grow. Then, talking with Jason right before the show, it became clear that my original idea was only part of the story, and so what you’re going to get, this conversation today that Jason and I have, when we’re talking about procrastination we’re talking about things like; what could procrastination actually mean? There are three traps. Which really, they are obstacles, but you’ll hear traps throughout, and apps and ideas and books and things that might help get a handle on our procrastination… if we want to… I say “if we want to” because I really do believe that there are people that thrive on that deadline, and the closer it gets, the more drive there is. I don’t necessarily think that’s procrastination. I think that’s a style. I think it’s a workflow, and for you personally, if somebody is telling you that you procrastinate, yet you come alive when you’re in that last little bit of time before meeting a deadline, it’s procrastination to them; so looking at what procrastination is to you would be very interesting; to be able to have conversations and to be able to show up in a way that you can say ‘Actually, I’m not procrastinating. Here is this work style. I understand what it may look like, but I’ll still get it done on time’. Or whatever the conversation that you have to have. Now, I am done doing the little bit of talking, because you’re going to enjoy everything that Jason and I talk about here, and I’ll see you on the other side.

Announcer (amid background music): Welcome to The Voice of Bold Business, the show that provides everything smart leaders need to evaluate situations, build relationships, and create solutions. Jessica Dewell candidly talks about the skills necessary to build tenacity, and do more with less. And now, here’s Jessica:

Jessica: It is your favorite subject?

Jason: I love procrastinating.

Jessica: Tell me more about that.

Jason: It is so much to do with ‘if I put it off long enough, will it accomplish itself?’, and then you get down to that stressful point where you just know that ‘I have to get it done’… and it puts that fire under your bum. The favorite thing I love about Mondays is knowing I don’t have to finish until Friday.

Jessica: Is procrastination a filter of sorts, to get rid of the stuff we don’t need to be doing that we think we need to be doing?

Jason: I never thought about it like that. I’ve always thought that procrastination was fear of success, or fear of accomplishing something. For those who want to procrastinate, maybe that’s a really good technique.

Jessica: I know, right? It’s like, how do we look at this a little differently? Actually, because I know sometimes there’s anxiety around it. It’s like there’s something that’s making me not want to do this thing and I’m putting it off. Whenever that happens, sometimes maybe I think it’s a mundane thing. Maybe it’s like, well this is going to be no fun, and so I don’t want to do it because it’s going to be no fun. But at the same point in time, it’s almost like, well I have all this other stuff to do, and here I am in this concept of making choices… and I’m making these choices to not do this. Maybe it’s because of a lack of clarity… and that crunch time at the end just goes (snaps fingers) BOOM.

Jason: I wonder how much of it is a lack of planning. 80% of your work is the planning, and 20% is the accomplishment. If that is, people just don’t know how to plan well… or maybe I don’t know how to plan well sometimes. I think if people sit down they realize that bits and pieces of planning will actually get your work done. It was like when we were growing up, they always told us in school to do an outline.  None of us ever wanted to do an outline, we just wanted to write the paper. I wonder how much of it could be that lack of planning.

Jessica: We’re touching on a couple of different things. Here it is, it’s the way I feel about it, the way I organize it, and then what do I do about it.

Jason: I spent a lot of time in my last year of college and kind of that summer after, I was doing strategic planning with the Department of Veterans Administration.

Jessica: Oh cool!

Jason: Yeah, it was really great. I think that experience taught me a lot about how not to procrastinate. Because they had business oriented people teaching me that the end result is not supposed to happen tomorrow, or the end results not supposed to happen next week, the end results supposed to be twelve weeks from now. How can we chunk it? How can we identify gaps and close it? Those types of things.

Jessica: Well let’s go back to planning, because I think that comes in to your example right there. It is part planning. It’s getting out of this concept of instant gratification. Which could be a part of procrastination as well. I’m not going to get the instant gratification because it’s one piece of this bigger thing. However, to make lasting change takes long periods of time, and being able to practice holding that complete path, thinking, I’ve decided this is 12 weeks out, or I don’t even know when this is, I just know I’ve got to move towards it. You know, something along those lines. Do you have any really good tips about thinking about planning and making an outline?

Jason: One of my favorite things that always goes back to what I’ve always been taught, which is the SMART goals.






Jason: By this date, I will have accomplished this percent of this task. It usually comes out to be a SMART goal. Those are still my favorite ways of chunking things down. But if you haven’t even gotten to that point yet, some of my favorite… as you know, I’m kind of like a technophile. I love all the different tools and software.

Jessica: Just a little bit of a technophile.

They laugh

Jason:  Some people do really well with Trello, with organizing cards. My personal favorite it Todoist. That one I like because I’m still one of those type of people that like to write things down. Todoist allows me to do it and sync it to my phone and it does it just like a checklist. So that is one of my favorite tools to do that is put my goals in to…

Jessica holds up sticky note pads

Jason: Oh, you’re a sticky noter.

Jessica: I’m a sticky noter, and I have like 12 different colors of stickynotes… because I use them all.

Jason: I grew up in a sticky note house. My parents were sticky noters. If they needed us to do something, say drop something off at the vet or something… they would put a sticky note on that, they would put one on the front door, and then one on our steering wheel.

Jessica laughs

Jason: You know you get in to that groove… oh three times is the charm, I’ve got to do this. You know that’s a great technique too I think, if you’re one of those people who needs to have constant reminders. You can sticky note things and leave them throughout the house. Another good trick that I really like is… I’m a visualizer, when I plan my events I like to think of them… but one of the really good techniques that I’ve done a few times, but it works really well for people who do not visualize well, is to leave yourself notes just in your surroundings throughout the house, and then when you’re out doing your task, you think, okay when I go to the bedroom I have this task, and when I go to the bathroom I have this task, and the kitchen is this task. You kind of turn it in to like a chore list of your house. But you’re really out at work or on the road or doing whatever you do.

Jessica: That’s why I use sticky notes. I have to create the things I’m supposed to do. I say I have to. That is what I have found. If I write an outline, it’s like, great, what do I do with this outline? This makes no sense to me. I have this stuff on a piece of paper now, it’s like I have this checklist, and I don’t do checklists.

Jason: Do they get overwhelming?

Jessica: Yeah, for me they do. It’s almost like, I just created all of this structure, and I’m not good with that. So the sticky notes and the creation of this thing I actually can have this… I’m building that vision, and then I can work for that vision and I can move around within it and jump around to get to the whole end goal, based off of different times along the way. When I work with my team, it can be really hard, because my team loves project management tools. I’m like, I will try.

Jason: Things like Trello and stuff.

Jessica: Exactly. We use Asana. There’s a purpose for that. When you’re organizing a lot of people, even if somebody’s out there like me thinking ‘yeah this is too much structure’, collecting that information right… Basecamp is another one… collecting this information in a place where everybody can come together, they can get what they need when they need it. That’s a really important piece I think as far as planning and procrastination. I’m a leader, right? I run my company, and I don’t like to-do lists. I shouldn’t say I don’t like them, they’re overwhelming. I avoid them. My desk is filled with piles. I’ll go through it and say, ‘Yes, no, yes, no, yes, no’, and all the stuff that I thought I wanted to do that sounded cool at one time, that has just become a task that’s outside of the realm of moving the company forward, or the project that I’m working on forward, or developing my team more, goes. It’s being able to clean it out too and not be held back to be able to say, ‘Yeah, it was a good idea at the time. Now that it’s been sitting around, it doesn’t actually really fit’.

Jason: Are you familiar with the ‘Getting things done’ method? Do it, delegate it, or discard it. I think what you were talking about is very similar to that. You have these piles, but really they’re like inboxes.

Jessica: They are, yeah.

Jason: I’ve always been a fan of having just one inbox. One place for all my personal, my work, my clutter, anything. I go through it. Do I need to do this? If I need to do it now, if it takes two minutes, I’m going to do it. If it doesn’t take two minutes, I’m either going to delegate it, or I’m going to plan it. That’s the other one. Do, delegate, plan or discard. Or I’m going to throw it away.

Jessica: I have to actually physically put stuff together to create the vision of what is going to happen. It doesn’t matter if it’s the week, it doesn’t matter if it’s a six-month long client project, it doesn’t matter if it’s a two-year business initiative. I still have to have it created. I actually have to create that.  Then I can think ‘Alright, now how do I feel about this?’, and every action I can actually say, ‘okay, I know this is going to move us forward. How do I feel about that?’ Then from that, it tells me it might not be the right thing now, or I need more information, or I know there’s something here…but.

People on my team, they’re just like ‘give me the checklist and I’m going to punch this checklist’.

They laugh

Jessica: We’re going to have to have a conversation and you’re going to have to make the checklist when we talk. I’m totally happy to help you achieve that. Knowing how we can work together and using those strengths to make that happen.

When you’re approaching planning like this, how do you approach it?

Jason: It’s not a photographic memory, but eidetic memory. I’m able to relate things based on a memory, and recall them very well. So I do a lot of planning in my head where I create a timeline, and I’ll kind of see where it needs to go. Now, I need to chunk those down on the paper.

Jessica holds up a sheet of paper with multiple sticky notes and lots of notes written on it.

Jessica: You do this in your head?!?

Jason: Yeah, I do that in my head.

Jessica: Holy macaroni! What a cool strength!

Jason: It’s probably the coolest thing I’ve ever been able to do, because I can’t play sports.

They laugh

Jason: (Jason demonstrates with his hands) I chunk those things up like that, and it’s never the exact date like your paper would say, or the exact task of a sticky note… you know, I say I’ve got a plan here, then when I get into the planning, I’m going to do this. But I also have to remember that part of my planning is call somebody, and then I’ve got to put something in to action. I think of all those, so I take very short notes in my to do everything. Not so much tasks, but where to find the information for the tasks. I’m a big fan of, like I said, those inboxes that you have. I have them digitally. I use a program called Raindrop where I can tag all of my resources, all my content, all my images, all my documents. It’s It’s 19 bucks a year. Super super cheap. I think it’s like two something a month. School… I would still be doing my documents, I could organize them in there, and you can tag it all. In physical paper form or anything else. I think folders work really well, or hangers or anything like that. When it comes to digital I think of something like content, like my social. Something might be an email template for me to use. It also might be an email template that I want to broadcast or get out to people. Do I want to copy that and put it in two different folders, or do I just want it in one place with two different tags, so when I’m searching for it, it comes up. Tagging is becoming, in the digital world, the smartest way to get through the whole folder jumble of multiplying all your documents and the ‘Where did I put it? Where do I keep it?’ It doesn’t matter, it’s just in one spot, and it comes to you, if you need to use it or don’t need to use it. Whatever you need to do you tag it immediately. At least to a few that you can find.

Jessica: You know that’s how I use my computer. I just put stuff in one place, whether it’s a Dropbox or it’s Google Drive or it’s whatever other cloud service we’re connected to. When stuff is everywhere I go there, and I title things and I will make notes with very specific things in it, so I can search inside every document, everywhere to get something. I have done that for years, because everybody organizes stuff differently, and if you’ve ever… I mean you work on a team. I work with teams, not only in my business but other places and I think that’s actually one of the biggest things that can accidentally and unknowingly get in the way is that everybody files stuff differently. It doesn’t matter if you have rules and stuff like that. There’s still this subjectiveness about it and you’re right, you end up with two or three copies because I want it here, but you want it someplace else but it makes sense over here just because we need the record of it in this place over here.

Jason: I think as a team it’s really important to sit down and strategize of how the team wants to do those. I have a way of doing stuff for myself, and then we have a way of doing things with at work. At Ritekit we do everything in Asana. Whether it’s a bug, whether it’s an idea, whether it’s a to do, we get it in to Asana. That’s our thing. For me, I have my tasks go in to Todoist, my documents go in to Raindrop, my personal files go in to Google Drive. So that’s a little bit different. When you’re on a team it’s okay to segment in a way, as long as you keep your personal and your work separate. You don’t want to put work documents in to your own personal stuff and have nobody be able to find them if they need to do something with it. The best way to do that is always to involve the group or involve the team.

Jessica: Everybody you are listening to The Voice of Bold Business Radio. We are talking with Jason Michael of RiteKit. Our program today is titled Flipside of Procrastination.

I love everything that we’ve been talking about so far. Individual organization, how does that tie in to this team concept? Because it always has to. It has to tie in to the bigger system that we’re a part of for it to work and not have obstacles, and reduce stress and other things. If you think about Simon Sinek and his ‘Know your why’ concept. We’re in a job, we’ve got this responsibility, we have this thing to do, we are one piece of a larger team, we’ve got this thing that’s due, and everybody’s relying on us. It’s really important, and I may or may not like it, I may or may not be afraid of it, I may or may not feel like I might let people down, yet I still have to get it done. Now we’re talking about these traps that we fall in to that make us procrastinate. Not because we’re procrastinators, but because we’re getting in our own way.

That first trap that we could talk about is this anxiety of a task. I know you’ve mentioned that before. How do you deal with having task anxiety?

Jason: First I want to at least broadcast this book that I had at one point. It’s a real short kind of ‘how to get out of your own way’ thing. It’s called Get out of your own way; Success is right behind you. You can get on Amazon, it’s like a couple bucks I think. I got it at a conference.

Jessica: I’ll link to it.

Jason: It comes down to not being the smartest and the person to get everything done. It comes down to, can you find where things need to go, can you find your resources? I’m a big fan of that resource planning. The best way to get out of your own way I feel is to keep things organized so that when you are working, you don’t distract yourself. Distractions are a huge part of procrastination. If you can get all your resources in line and all your resources in order, you can work towards all your goals. Then you know what to fall back on, you know where everything is, what you need to lean on, and then you don’t get yourself distracted.

Jessica: I’m sure you have similar things… where you just go from meeting to meeting, and you think ‘when am I actually going to get to create something? When am I actually going to use the stuff that I’m gathering in these meetings to further what we’re trying to do here?’ Then I lose my motivation. I have to wait too long, and the moment is gone. Do you experience that too?

Jason: Yeah, just like you said… you do things in small chunks and you take a break, small chunks and take a break. If I go any longer than 45 to 50 minutes without taking a break, even if it’s just to stand up, walk around my desk and sit back down, just to clear everything out… your eyes, your head, everything… I start to lose my motivation. For me, it’s eliminating distractions by giving myself planned distraction time.

Jessica: For you… does a lack of motivation show up as avoidance?

Jason: It becomes and anxious thing to me. I feel like I’m never going to get around to getting that task, and that’s how it manifests itself.

Jessica: Let’s talk about the third trap… which is the fear of actually doing amazing work.

Jason: That, I don’t know where it comes from, but it’s almost of… I don’t want to say it’s a fear of responsibility… I want to say it is a fear of… once you start things going, will you be able to keep that momentum going? It’s that personal motivation, that personal drive. If I start now, will I still be successful later? I don’t know how it manifests itself thought. That’s one thing that I can never figure out. Is it a part of being a “millennial” that made me that way, that I’m just afraid of the future, or is it something else? I haven’t quite figured that one out. What do you think?

Jessica: A lot of self-exploration on my own, and coming up against whatever obstacles I put in my own way. Because really, a lot of the obstacles I walk in to headfirst. It’s like ‘Oh! There’s a wall there!’ Why didn’t I see it coming? Well I did, and I chose to go forward anyway. There is this thing of being noticed, and what being noticed means in the culture of an organization. Whether that’s in the family, whether that’s at work, whether that’s in our community, it doesn’t matter. There are some people who thrive on being the center of the limelight, which is interesting because some people would put me in that category. I can be a ham, I can stand up and I can talk, I can talk to anybody and any stranger… yet when it comes to work and actually taking the stuff that I’m sticky noting out in to visual processes and getting it done, I get to the very end and it’s almost like I know it can work, but I don’t want anybody else to know I can know it will work.

Jason: Yeah!

Jessica: Because I don’t want to stand out that way. And that’s a conditioning thing. Now we’re talking some of it might be personality, a lot of it is conditioning and how we think about ourselves. This is where it goes back to this concept of ‘success is right behind you, all you have to do is step aside’. Concept of this book. For me it has no personal drive. I have tons of stuff around that I have created that will never see the light of day. It’s almost like artists are similar to that too. They make all of this stuff, but they only pick a few things. I know I always pick the best. Whatever I’m going to do, I’m going to pick what I have that’s the best at that time. But sometimes people don’t. They pick the runner-up because they don’t want to be seen as whatever they want to be seen. So we’re living in this interesting dichotomy where when we are creating our own brand and we have this knowledge base and we have these connections and we’re fostering these relationships, we don’t want to stand out. We want to continue to be accepted by this group. That’s kind of where my brain goes, and a little bit of my own personal self, but also what I’ve observed in business owners in leadership teams that I have seen.

Jason: Yeah. I think the fact that you brought that up, my mind started turning immediately to Brene Brown. She’s a researcher psychologist who does a lot of research on shame and how to get through it, and surprisingly a lot of people, whether they have good pasts or bad pasts, good futures or bad futures ahead of them, a lot of people experience shame differently. She has a really good Ted Talk that is called The Power of Vulnerability. I think that is one to listen to, because it helps give the background, and the pieces of ‘Why am I afraid of being vulnerable?’, because it puts you in a spot of vulnerability when you’re in the limelight, and then that kind of transitions in to ‘Well, I’m ashamed of…’ and it doesn’t always have to be very deep hardcore shame but…’I’m ashamed of my personal abilities.’ It’s like when you meet people you think, does this look good on me? I feel like I’m fat. Those small little pieces of conditioning. Those small pieces, they can get in to your brain, and they stick there for a long time.

Jessica: If I have something to say, I’m going to say it with every ounce of my being. I believe it to the core… even if it’s dead wrong. (She laughs) Sometimes I’m actually making this stuff up. Like I said, I don’t do this much anymore, but in my early 20’s people would say, “Really?”, and I would say “I actually really don’t know, but you asked for an answer and I’m giving you one”. And I’m going to say it with confidence. Being able to pair this idea of taking these skills like this confidence that I have, but actually being able to say “I don’t know.”, as well as “Here is the answer”.

Jason: I wonder how much that comes back to… we were talking about instant gratification. Is it okay to, when you’re finding the answer come up with something and your hypothesis turns out wrong and then attacking those, and those thoughts of ‘Well I wasn’t right when I started, how could I have gone down this track and been wrong the entire time?’

Jessica: It starts early by the way. I was having a conversation with my son on the way to school, and he’s telling me about bees. He’s telling me about how bees use all summer at the flowers to make their food so that they can survive the winter. I said, “How cool! Where did you learn that?” He said, “Oh, I just know it.” I was like, we don’t just know it. Then he says, “Oh yes, I just know.” I said, “Well by listening to your Mom and your Dad, and your aunts and your uncles talk, you eventually decided you wanted to try too, and you talked on your own. It came from us talking to you, and around you, so you learned it.” He said, “Nope! I just started talking.”

We are all interconnected, whether we think we are or not, and you’re right, this idea of… can we this instant gratification… and an expectation. There is an expectation on a lot of people to have an answer. People weigh the word, and the questions are phrased ‘I know you have the answer so give it to me’.

Jason: And if you are wrong, they want to oust you immediately.

Jessica: Then it jumps back in to this probably it’s either a lack of motivation or back in to this anxiety of ‘Holy crap I’m going to be ostracized.’

Jason: It could be a really big part of it. A lot of our government leaders… and anytime somebody makes a mistake, the internet is saying ‘kick him out, kick him out, end their career’. It’s never ‘let them fix it, let them focus on this’, it’s ‘How dare they have done something wrong?’

Jessica: It is up to us to, as a leader, and ourselves and the people that we surround ourselves with to hold the space. When somebody makes a mistake, just notice it with them. Acknowledge it with them. Then, it’s okay, so now what? Now what?

Jason: Right.

Jessica: We don’t do that with kids in general. It does not happen in school. I mean, think about every test we have. You either are right or you are wrong.

Jason: You have to be right or wrong.

Jessica: Right or wrong, right or wrong.

Jason: Like you said, you’re right or wrong, I start thinking of a grade… A or B, if you have a C, that’s still not acceptable if you’re part of middle-class society. Just approaching that from a different mindset that people are allowed to be wrong. You are allowed to be wrong. You are allowed to not have the answer. When you make a mistake, you are allowed to say oops, and let me correct it.

Jessica: Responsibility. By the way, I don’t know if you heard it everybody… he said when I make a mistake, let me correct it. Whew, personal responsibility, I want to point that out because that is a very valuable skill that will work in any relationship, especially in businesses.

Jason: If you make a mistake, and you notice it and you run away from it, you won’t be moving forward. Because then it’s always going to be… ‘well Jason just keeps making a whole bunch of mistakes’, rather than ‘well Jason fixes everything he messes up. At least he tries and knows not to do the wrong thing now.’ You can use those as learning lessons too… the next time you approach that task or that situation or that issue, to remind yourself that you made an oopsie last time, don’t go down this path, or don’t do this one thing.

Jessica: Jay was one of the bosses early in my career. This company bought my company. He was part of the leadership team at Digital Rivers that bought the company that I was a part of the leadership team of. I worked with him a lot. For lack of a better description, just visualize this, I have a very long leash. I had a very long rope to go out, and when I got to the end of that rope, it was very clear. I was done, stopped, come back and do something different. The concept being though was, okay, I know if I let you go, because he knew me very well, which was ‘I’m going to let you go. You’re going to accomplish great things. I’m going to develop this, and we’re going to use the lessons, when they make sense, to help shape who you are’. I never felt judged. I didn’t like some of the things he said, but that’s okay. I never felt like I was wronged or I was in trouble or any of those things. I model what I do off of that a lot, and I shaped how I react to situations from that because it was the first experience of holding a space… like when you baby-proof one room in the house, or you put up gates so small dogs or big dogs stay in one area that they’re supposed to. They’re not going to get in to trouble because that space was set up for them to do what they want to do and be who they are. Babies, dogs, and so we have to do the same things in our businesses. A whole business, and now we’re talking about business culture.

Jason: The old mentality of ‘Do as I say, not as I do’, it doesn’t allow your employees, it doesn’t allow your leadership, it doesn’t allow anybody to develop themselves and learn.

Jessica: Right.

Jason: Just because you told me the stove was hot… I don’t know it’s hot until I feel it myself.

Jessica: I love that metaphor of ‘I don’t know until I’ve experienced it myself’. That comes down to the fact that whatever our… and I’m calling them traps, but realistically I don’t think they’re traps. I just think there are things that we tend to do because we either don’t know any better, or we were modeled, or who knows what else it could be. This concept of having anxiety around something, having a lack of or having a fear of success when it comes to motivation, which makes us fall in to this realm of procrastination. Among other things. Like this whole concept. I’d have to really think more on that whole filter piece to find out what that is. I know there’s something there. I’m not sure where to take it.

For us here, as we’re wrapping up, one of the things that I know I wanted to come back to is this concept that we can change. Now somebody else may look at us and see a procrastinator. However, we can change our efficiency. We can change what we do. We can change our relationship with the concept of procrastination so we are affected less by anxiety. We’re affected less by this stuff.

Jason: Yes. Absolutely.

Jessica: I want to know a little bit about when you were in college what were these things that happened…

Jason: Oh my gosh. Can I even admit some of them?

(They laugh)

Jason: No I’m just kidding.

Jessica: Well remember, this is going to be aired, so it’s up to you how much information you share.

Jason: I think back to my college days, and I think about my responsibility levels… or irresponsibility levels… and I’m not talking about college kids who party. I was never really one of those crazy type wild people, but I’m thinking of the responsibilities of how I would approach my homework, how I would approach my relationships with people. My homework I always thought I could do it last-minute, because I had been doing that my whole life in school, so if I do the assignment last minute I will get it done. Then I got a C, and I was like, oh, you know, maybe I can’t do it last minute. It was when I hit that roadblock, or trap, that taught me to go back and correct that. I started using that behavior towards the end of my college career and in to grad school a little bit. Once something is assigned, start exploring it, start figuring out what you need to do. Start chunking it together.

Jessica: There’s a lot of life experience and there’s a lot of learning in the sense of that natural consequence. When I did this, I didn’t like the outcome… so I could keep doing it and see if I get a different outcome and at some point it’s like, no, I still don’t like the outcome the way I’m doing it, so I’m going to try something different.

Jason: Einstein who said that “insanity is doing the same thing and expecting different results”.

Jessica: Yes, Einstein did say that. Exactly. I love this concept of procrastination. I’m not saying we should change you procrastinators out there. I like the part of me that is a procrastinator, because again, I think, and maybe this is a rationalization, but I think I filter better that way. Now, could I use that filtering in a different way to be more efficient like the story in the evolution that Jason was just telling us about? Probably. I’m just on that different path. As we are moving through organizations and between organizations, and we’re really looking at what we do, how we do it, and what contributes, it will allow us to better say ‘Yes I want that’, or be able to say ‘I want to be able to put my hat in the ring to be able to try that out’, or to say, ‘I know I’ve been assigned this, and I know you guys think that this is great…it takes all of my energy. I don’t know if I’m going to be able to get this one done on time. It’s going to be so hard.’ That’s just a self-awareness piece of ‘Why am I procrastinating?’ or ‘What makes me procrastinate?’ Being able to share it… going back to this concept of being slightly vulnerable. It is okay to say, ‘I’m willing to do this. I know I can do it. Yet, it’s going to take way more energy for me to do it than I’m going to get from it or the surroundings here.’ Maybe by saying it out loud, somebody will have an idea on your team that can guide through what needs to happen and how it can happen, so that maybe at least you don’t get burned out by it or you’re not putting it off because it’s draining in any way.

Jason: I could not have said it better myself.

(They laugh)

Jessica: We’re thinking about changing this habit from motivation and part of that is recognizing how we plan and what planning means to us. It also means how we organize, and what organization means to us, and being able to know how we do it versus somebody else, so that we can connect them together when we’re working on teams.

To me this concept of ‘The flipside of Procrastination’ is that it’s not a bad thing. It actually is a really important skill that probably has way more opportunity because if we can get rid of our anxiety around it, if we can make sure we stay motivated, an if we understand this concept that we might be afraid of the outcome being noticed… actually being successful. Once we got those taken care of… procrastination is amazing.

Jason: Well yeah. (they laugh) Like I told you before, it is my favorite part of the week. I wholeheartedly agree. It gives you all the opportunity to explore your motivation, your anxieties, your vulnerabilities. It’s what you do to move on from those. Exploration without action is not helpful.

Jessica: You’ll find all the program notes at, or you can go to and search ‘Flipside of Procrastination’. You’ve listened. Rate this program, and subscribe to The Voice of Bold Business Radio where you are listening to this program, so that you can have the new programs that air on Tuesdays and Fridays delivered directly to your listening que.

As a leader, you know, and you see procrastination. You might be graded by it, your employees might grate you because they procrastinate and it drives you crazy. Doesn’t matter. What matters is it exists. It’s something we deal with, and understanding the underlying pieces, and how they might be used to flip it around and use it for good, if you will, is a really important thing.

Add to this conversation and tell us in your shoes, as a leader in your organization, as a leader in your life… what do you do when you procrastinate, and tell us what your flipside of procrastination is.

Announcer – Subscribe at and get more information, program notes, and past episodes. Bold leaders approach each situation and focus on action to achieve a higher level of leadership. Jessica Dewell, your business advocate is the host of The Voice of Bold Business Radio. Thank you for joining us.