Using Calendars And Consolidating Software With Lindsay Halsey

Lindsay Halsey:

Thanks so much for having me here, Jennifer

Jennifer Bourn:

So, you’ve got more than 10 years of experience working in SEO. You help businesses get found on Google and help freelancers and agencies confidently offer SEO services. You’re an agency owner, a product owner, you volunteer, you’re an avid outdoors person, and a mom. Like, I need to know how all of this came about.

I want to know your origin story of how you got to where you are today.

Lindsay Halsey:

Well, I started in a pretty unlikely place, which was, I used to be a mountain guide and ski patroller, and I decided I needed to take a temporary change and try something new and I took a HTML/CSS class at the local community college. And it piqued my interest. I just wanted to learn how to build one website and use my brain in a different way because I was definitely in a very physical line of work.

And I loved it. And I started skipping powder days, which if you’re a skier, you know, is like very not the norm. Skipping powder days, I’m with my friends and working on the computer quite a bit. And I convinced an agency here locally, I live in Aspen, Colorado, to hire me, even though I had no job experience, and they did.

I printed out literally like a hundred pages of the internet. I printed out blog posts and all sorts of things, and I took them on my last guided climb on Kilimanjaro. And when I wasn’t taking care of my clients, I was in the tent thumbing through definitions of SEO and all these things, because I had a job that was very new to me.

Jennifer Bourn:

You are thumbing through printed pages of the internet on Mount Kilimanjaro.

Lindsay Halsey:

I used to tease my dad about doing it like printing the internet. It was not how it was designed. It was designed to like, be consumed in a different way. And then here I found myself trying to study up so that like on day one of the job, they didn’t figure it out what level of inexperience.

All they knew was I was a college kid with some work history, but otherwise nothing, no professional history in the industry. And I worked for that agency for three or four years. I learned a lot. I became the director of the department, and I really enjoyed the work because I loved problem-solving.

And if you engage in SEO, it’s a lot of thinking through problems and working with clients and solving an overarching problem, which is more leads, more sales, et cetera. But the part I didn’t like was having a nine-to-five and checking in and I knew I wanted to start a family. So, to give myself a little bit of a road map, I thought I’d leave my job.

And I’d started as a freelancer. And that’s really what I did. I happened to find a like-minded business partner who is a friend. And she was thinking of doing the same thing unbeknownst to me. And so, we teamed up and we’ve been working together ever since. And we started an agency and did that for a long while and still do.

And then we started a product-based company, Pathfinder which just took a different angle on what we are doing, which is helping businesses get found on Google.

Jennifer Bourn:

I love that you started your business with a friend like you both were thinking about making that transition and decided to go in and do it together. There are not a lot of people that get the opportunity to go into business and start something new with somebody that they already know. They like.

Lindsay Halsey:

We feel extremely fortunate in the professional world. I’d say meeting Lori and developing a business together was one of the luckiest breaks. And that when we look at what works between us, it’s really similar to what works well for me in marriage, with my husband, which is very values-driven decision-making.

And Lori and I have similar values around how much time we want to spend with our family and the importance of work-life balance. We have similar sort of financial needs of what we need to take out of our business. So, one of us isn’t trying to go somewhere the other person isn’t.

And so, we have just all these different areas of alignment. And I look at that with a little bit of yeah, we knew that but also a lot of it was luck. And the attorneys definitely tried to talk us out of a 50/50 partnership and basically told us nine out of 10 fail and knock-on-wood, I don’t know, 12, 13 years later, we’re still cruising along and getting along wonderfully.

Jennifer Bourn:

Well, I think it’s an interesting thing to point out that your financial goals and what you need out of the business were in alignment. That is a really big cause of friction and a lot of cases where one person needs a lot more income than the other or has larger aspirational goals than the other. And that mismatch can really cause some friction.

So, to find somebody who’s aligned on what you want to get out of your business, what your revenue needs to be, to be able to pull out the income that you want, and find that alignment is really incredible.

Lindsay Halsey:

Yeah, it was really incredible. And a lot of it had to do with phases of life, where we were with our families and having children and then now having older kids and starting to think about saving for college like that. So, a lot of it had to do with kind of some of the bigger picture pieces of our lives that had a lot of alignment.

Jennifer Bourn:

Now, you started your business because you were thinking of having a family, you wanted to do something different, you’ve gone through this process of building up your agency of starting a product of doing all this with kids and with a spouse who has a fairly inflexible schedule, the first 15 years of my life with Brian was spent working around his fire department schedule.

So, before I started my own business and I commuted to work. I only worked at home the days that he worked. So, we did this kid switch. I would load Natalie in the car in the morning, drive down to the fire department, drop her off, and leave her at the fire department with Brian. So, I could go to work, and he would load her in his truck and drive her home.

I look back on it and I think, what were we doing? But you just figure out these things that work for you and you get on with it.

So, you’ve gone through this process all while starting a family and raising your kids, and your spouse doesn’t have the most flexible schedule either. How do you both make that work?

Lindsay Halsey:

Yeah, my husband does not have a very flexible schedule. He works as a ski patroller in the winter, and he works as a bike patroller in the summer. So basically, he’s like up in the mountains and he’s leading teams there and helping them respond to injuries on the mountain and so I can’t call him and say, we have a sick kid. He literally might be, in the middle of something important. And so, he can’t run to the school and get the kids unless it’s a huge emergency.

And we knew this by design. And so, when we were starting what I would consider, like the freelancer world as we moved then in agency life and now in product life. In the beginning, it was relatively easy because my job demands were relatively low — and in those early years of having kids, I was only an agency person.

I didn’t also have the product business and that scaled over time to where we are today, where I’m running two businesses and his career continues to grow and build, and his time commitments are getting more and more fixed. There is a lot of scheduling and scheduling matrix. And that is not very fun for anybody that’s been there and can cause some stress.

But for the most part, we come back to remembering a few things, which is one we do better because I love picking up the kids from school, and so that is the priority for me. And I get a little envious when he gets to do that. And when I’m in the office till 5:00 or 5:30, we’ve tried to go back to our roots of remembering that I was the one that stepped into a more flexible job for a reason, and then I give the hands up for the high five when I really need a hand.

And so, we had a last-minute snow day, it’s April last week and my kids didn’t have school. And I was doing a webinar with 60 people and I can run a business meeting from time to time with a kid in the background, but 60 people on a webinar. I can’t do it. Even if they’re pretty well behaved, I just can’t do it.

And so sometimes it’s just a matter of raising a hand and saying, you know what I can take the sick kids or the snow days or the school pickups most of the time, but I hit a roadblock I can’t today. And then having my husband, match me in the middle and say, okay I’ll do the first half of the day, you do the second and we’ll make it work. So yeah, we’ve made it work. But systems calendars, all those things are really a big piece of the puzzle. And then a lot of communication.

Jennifer Bourn:

I love that you said calendars. My calendar is what we live and die by in this family. I was never really a big calendaring person when I was younger, but we got into the habit because of Brian’s fire department job.

Everything got scheduled in December for the entire following year, every vacation, every holiday, they picked it all the first week of December, and then that’s what we were stuck with. And so, our whole life revolved around that rotating schedule and the calendar being built around that.

You’ve got webinars that you lead. You’ve got training. You’ve got your agency work with clients and product support. How do you manage all of that in terms of scheduling and organization and calendars?

Lindsay Halsey:

So, I use Google calendars and I have a calendar that matches each one of my emails, which sometimes feel like different identities, right? Like a personal email, my webShine email, my Pathfinder email, and then my like volunteer work email. And I am very meticulous about calendaring things into the department they fall in, and I love the layering system where I can see them all and the sharing you can do between calendars.

So, all my different identities are a master of all of the calendars. So, I’m never having to log in and log out and do something weird. But I make sure that if it’s a webShine client services meeting, it’s in the orange calendar, which is for webShine. And that if it’s getting on a podcast or doing something that I’m doing for Pathfinder marketing, sales, whatever, it’s in the blue calendar, which is Pathfinder. And it’s the same for our family’s personal calendar. And I do that just so that I can overlay things and at the end of a week or the beginning of the week, I can very quickly see where my time is going.

And so, when I feel overwhelmed, when I feel over-scheduled, the really simple piece of color coding is to be like, oh, wow, I have a lot of agency commitments this week or coming up and so what am I going to do there? Am I going to try to offload some of that work to somebody else? Am I going to, then block out some focused time for Pathfinder down the road?

I really love knowing where my time is going, because one of the least satisfying places to be, getting pulled between different roles and responsibilities is where at the end of the day, you have no idea what you did and you have no idea how you’re going to get through tomorrow’s schedule because they’re all totally in congruent pieces and so I like meticulous calendar managing.

Jennifer Bourn:

Oh, that makes my heart so happy — and the fact that you color code. We have a giant three-foot by four-foot wall calendar that’s color coded and I know if I look at it and there’s too much of one color in one ¬area that we’re going to have a problem.

Lindsay Halsey:

Exactly or one kid is getting too many things, you know, we’re all of my son’s activities. If my daughter doesn’t have, space in the calendar and things like that. Yeah, it’s very helpful. Or I haven’t checked in with my team and our Pathfinder team do I have time for everybody there? And color coding is essential.

Jennifer Bourn:

Oh, my gosh. That is so my jam, I can’t even tell you.

So, I want to touch on something that when we were originally talking about this podcast, you had sent over a little bit of information. And I want to quote you on one of the things that you shared, you said “I was doing nothing well and jumping between the needs of everyone but myself and still feeling like you were letting your team down.”

As much as we put our best intentions forward of having strong calendars and making strong schedules when we’re juggling a lot of different things — work, family, life teams, and all of that. It can be really hard to continually stay on top of things. We set the best intention, but sometimes we’re not perfect with it.

Where do you find that overwhelm starts to creep in where you need to say, hold on a second, I need to course correct?

Lindsay Halsey:

Usually, it catches me too far down the road. So, the overwhelm is there and I’m humming along and Yeah I got this and then there’s always a breaking point. There’s a snow day, somebody gets sick, and all of a sudden, the systems fall apart. And there’s no backup plan.

And so, I think I’ve hit this place multiple times, for various reasons. Sometimes they’re personal, like overwhelmed because I have a newborn baby and I’m balancing that with work or where I am now with grade school-age children, where I’m balancing those demands with work and growing two businesses now.

And so, for me it’s trying to get a little bit more proactive on identifying before the overwhelm kicks in — Hey, this is coming, something is about to fall. But it’s about having time ultimately to do my work.

So, I love working with people and I love having meetings with people on our team. I love having meetings with clients. I love taking my son to piano. But everything needs to also have then the time it’s going to take for me to deliver on whatever my responsibilities are. And so, one tool I’ve been using, and this is still talking about scheduling, is giving myself time after meetings.

I always gave myself a little time before a call for like preparations. So, a half-hour before a call so I could get oriented but sometimes then I would just go into the next thing. And that was really unsatisfying for me because I would come out of a call usually with a couple of things, I need to do to move the needle forward or take action on whatever we talked about, and the best time for me to do that was right then and there it’s fresh in my head.

And so now I’m starting to buffer that into my scheduling, which is to say, okay, a call has post and I can predict the post. Like, is it 10 minutes or is it an hour? Because I met with a client, now I need to go do my thing and get it over to other team members and things like that.

And so, my meeting blocks in my calendar are pretty large, but a lot of times on the agency side, it’s my only customer touchpoint. So, I’m meeting with the client and then I’m doing the thing I need to do and then my team is taking it from there and I don’t have to go back to that project.

Jennifer Bourn:

I love that tip.

Yeah, so many times we do plan. Like I’m going to set aside some time for prep before a meeting, and then we jump right to the next thing, to the next thing, to the next thing. Having that little bit of time afterward to organize your notes, organize your thoughts, and get that one action item or those couple of things done to empower the rest of your team to go before shifting focus — it’s such a powerful habit to get into.

Lindsay Halsey:

And it’s satisfying. The way I was ending my day. Normally it was like a big, long list of notes of everything I talked about. And maybe I had four meetings and then I’d run out the door to go get my kids from the bus. And then I do after-school activities and cook dinner and start to unwind and it’d be around seven and they’d be doing their thing — and now I would have all of this follow-up to go do. And that was really unsatisfying.

I’d forget — even with my notes — one of the meetings because I was pivoting from services to marketing Pathfinder to something personal. And so, this way, I feel like, at the end of the day, I am having more days where, when I go to bed at night, I have a concrete sense of what I accomplished. The list may not be as long as a list of different things, but each thing actually got done and that’s more satisfying.

Jennifer Bourn:

I totally relate to the idea that you were reaching the end of your day with this giant list of to-dos to follow up. When you start your day with to-dos, and when you end your day with to-dos as well, it really makes you feel like you didn’t get anything done all day. Or there’s this sense of dread a little bit of, oh my gosh I have to do all of these things or follow up on all of these things before starting the next day or before I quit for the day.

So, I really loved the idea of closing out something completely before moving on to the other. So, you aren’t left with this big pile at the end of the day.

Lindsay Halsey:

Exactly. And so, I spent a lot of time planning my week and looking ahead at my week, and making sure that I’ve structured it accordingly. I just moved an internal meeting tomorrow by an hour because I realized how things stacked up. I was missing one of those blocks. And it is a lot of calendar management. But I know what the thing is that I need to go do to wrap this up and to feel complete about it.

Then because we had started different businesses at different times, because we have people playing different roles at different businesses, we had a hundred different tools. And so, whether I sent the person that’s going to work with me or made the note, or I did whatever… It might be Basecamp. It might be a Google Doc. It might be a Trello board. It might be… I think we were using Process Kit. It might be in Notion or you might have to dig through Slack

Jennifer Bourn:

Oh, my gosh. I feel seen.

Lindsay Halsey:

And you’re like, Oh, each one of these things had very defined tools and is very good at what we were using it for. But then I was passing things along to team members in all these different places and they were getting overwhelmed. And so we had some major systems inefficiencies by being on multiple platforms.

So, my most recent total overwhelm was that the whole team was overwhelmed because nobody knew where anything was or where the to-do list lives.

Jennifer Bourn:

The too many tools bit of overwhelm. That struggle is real. And I think it’s almost worse for people who work digitally all the time — remote workers, tech workers — because we have access, right? Our awareness of tools available is so much larger and we get this bright, shiny object syndrome of I should try that, and somebody else said this was really great, and we should try this, and then all of a sudden, you do have this fragmented bit of data across your business. Some stuff is over here, and some stuff is over here and some stuff is over here and that overwhelm really is serious.

Lindsay Halsey:

Then I was getting into like, well something else to drop. I have to quit one of my jobs and quitting your job when you’re self-employed means something different than when you’re employed. Quitting your job when you’re self-employed means ending a dream or something really big. And not that it doesn’t if you’re an employee, but there is that piece where it’s like, no, I started this, I want to see it through. That’s really my most recent sort of getting overwhelmed, getting stressed out, and then starting the questioning laundry list in your head in the middle of the night.

I don’t think I saw around the corner until we started doing it how much importance was for our team at the time on the toolset and going back and rebuilding that where you feel like, Hey, I don’t have time to go do this I’m overwhelmed. I don’t have time to change toolsets or to rethink my toolset but what if the toolset matrix is actually contributing to the overall feeling of being overwhelmed because it wasn’t as organized as those nice three calendars I was talking about that had the color code overlay.

It was really messy.

Jennifer Bourn:

Well, what an aha moment of just saying, what if it is the toolset that is causing this — when you had that moment of realization, that it might be all the tools that you were juggling.

What was your first step to take action on that and figure out, was it one tool? Was it all of them? Did you need to condense and get rid of some?

Lindsay Halsey:

So, the fun part of working on a team was this was a collective meltdown, so to speak. And so we could jump on zoom as a team and all complain a little bit about what wasn’t working for us — and we all nodded at the same things. So that was nice. Just being open and honest with the team and then getting the dialogue going and finding that, hey, I wasn’t alone.

And the next thing that we did instead of going back into our existing tools and talking about what we liked and what we didn’t like about the tool, which really are things we can’t control. For the most part. We talked about what we each needed to manage our daily work lives.

Somebody on our team needs a way of managing client services and we are able to keep track of tasks under projects, and these things are repeatable, but they then have different statuses, right? So, something needs to be done, something is in progress, or something is in completion mode — and that was his application of mostly what he needed for project management.

Somebody else needed a way of managing sales leads and following through with a lead and turning them into a customer, and that’s a very different use case. We have contractors that work hourly and need to be able to time log and that’s very different than our teammates who are employees and don’t have to necessarily log their time into buckets to get paid.

Talking to the team and really rearchitecting from the very ground up how we all use things and actually doing a lot of screen-sharing because the way I click around something and the way I do something, isn’t how the whole team does it was what we called step number one.

So, we identified we had a problem and then I just took 15-20 minutes with each person to be like, what do you do?

Jennifer Bourn:

I love that. The fact that you took the time to look at the people on your team and how are you using these tools? What does your workflow look like? How can we make your daily life better? Not, hey, we’re going to sign up for this tool, we’re going to condense everything over here, go learn something new.

I mean, what a fantastic place to start?! To not only say, hey, we value the work that you’re doing, and we want to empower you and pick something that’s going to help, but to get them involved in the process and then have team ownership over that… Did you find that they were more enthusiastic about the changes?

Lindsay Halsey:

They were. Everybody was pretty enthusiastic about the changes. And having a little buy-in was really helpful. They were overwhelmed too, so they’re like, I don’t have a lot of time to change tools. But as soon as we really got into the high level, how people were using it, you start to get buy-in. And then from there, we’re actually at CaboPress at the time, and we started asking other business owners what tools their teams were using and we got all sorts of different feedback from different people.

Out of all of those tools, ClickUp was what stood out as being the most flexible for our team and having the ability to do each of these different team members’ work processes all under one roof. I think there are a lot of great other tools and Asana kept coming up. And so, then we researched that a little bit more.

I did a demo, of course, which I like to do every time, and then it was really time to start to build it out — which was also a pretty big project. When you have six tools, you’re trying to bring them into one.

Jennifer Bourn:

Oh, yeah. That reconfiguring and condensing all of that into one platform. I can only imagine the amount of work that had to go into that.

Lindsay Halsey:

And in the case of ClickUp, it’s a very overarching project management tool, which means it’s super flexible, which is what we needed, our first inclination was to go in and let each team member build out their workflows. You know your work best, so you go do your section, Jennifer, and I’ll go do mine, and Lori will go do hers, and then we’ll all meet and we’ll have it all built out.

We were cautioned early on that wasn’t the best strategy and so instead, I built the whole architecture infrastructure — how it was organized. And then along the way, did another check-in with each team member to get some feedback on the piece of it that would most apply to their daily life.

The reason we did that is that there are multiple ways to do the same thing and one way isn’t necessarily a lot better than the other, but we don’t want to have to relearn when you’re in this space for marketing, we do it this way, and when we’re in the space for customers, we do it that way.

We wanted to have one-way and that meant one person building it out. And that’s worked really well too. Everybody has some buy-in in the tool, but nobody comes in and just creates their own whole world and comes up with their own way of doing things because there are so many different kinds of approaches you can take.

Jennifer Bourn:

I really like that notion of establishing the company way, the Pathfinder way, the webShine way. This is how we’re going to do this. And that way, that consistency through is also going to have a ripple effect in terms of bringing on and training new folks as well. Have you seen it streamline and make things simpler across the company?

Lindsay Halsey:

Very much so. So, today’s Monday and I was looking ahead at our May and June planning. And so, we have our content plans and our webinar plans and things we need to do for customers, and we have a vision of all those things. And now it’s just so quick and easy to have a meeting and review this broader strategy and then make sure everything is in ClickUp and ready to roll in.

And so, when you click the, add a task button under a blog, post it as the five steps, it takes for us to get a blog post out. So, it’s really quick and easy and so I really do feel much more organized I can sit down and layout in a short period of time, a lot of strategic thinking to make things very actionable for the whole team. And other people can pass back feedback. Yeah. It’s so it’s going great. Now that the system is in place.

Jennifer Bourn:

So now you have one centralized location, one centralized tool. Do you find that initial bit of overwhelm where you felt like you were dropping the ball — I mean, sometimes we’re not even dropping the ball, but we feel like we are — that’s gone away now that there’s greater visibility over what’s happening and what’s going on throughout the company.

Lindsay Halsey:

Yeah. I feel less like I’m dropping the ball for people where I know, oh, there’s nothing I need to do I don’t even know what list it’s on kind of feeling. So now it feels very orderly and organized, which just feels good. But we’re finding just more efficiencies across the board, in both businesses. Now that we’re managing our accounts this way and in our campaigns. And yeah, that’s leading to a lot more just feeling good at the end of the day.

On a Monday we all have a plan for the week and on a Friday, we can wrap things up and really actually document: What did we do this week? And feel like we’ve closed some things, marked whole sections, not just a small task but something large, totally off the to-do list and that’s pretty satisfying.

Jennifer Bourn:

And how has that effect transferred through to your personal life, your weekends, your family life… because we carry the burden of the stress of business. It doesn’t all of a sudden, just because it’s five o’clock, shut off. So how has that changed things for you and the outside hours?

Lindsay Halsey:

So, I got in my like seven to eight o’clock hour back in the evening, that time where I used to have to go through my follow-up list. Now, it’s all in ClickUp. It’s all organized. I’ve given myself the time to do the work. And so, I feel like I have that hour of the day totally back. And I’m more often than not getting back on the computer.

I might check my email on my phone just to make sure there’s nothing huge, but I’m not having to get back on my computer to do the thing that I said I was going to do that day — something that somebody is waiting on. And that has been huge for family life because the reality is from seven to eight at night, I’m pretty tired and I’d like that to be my own time. Whether that is to goof around with my kids or to go start reading a book or something like that. That’s been one really distinct piece.

The other is, I feel like when I do work on the weekends, which I do my favorite way to work on the weekends since I have young children at home is to actually leave the house. So, you won’t really find me in my home office on the weekend. If I need to put in weekend hours, I figure out where it’s the least burdensome on the family, and where I’m going to feel the best about it. Usually, that’s kind of Sunday, late afternoons when maybe we don’t have as so much going on.

When I go to the office and I have three hours, which is about the max, I’m willing to work on a weekend, I feel very efficient with that time. So, I actually can get through a lot of things because the to-do list is so well organized. And so well-structured that I actually can use that time wisely. Whereas before, sometimes I felt like I was doing like an hour and a half of project management to do an hour and a half of work.

Now I feel like I’m just getting three hours of work done and I can move on and that’s been huge.

Jennifer Bourn:

I like the distinction between choosing to work on the weekend and not being in a position where you’re forced to do that. That’s a huge difference. And being able to say, I’m going to choose the amount of work I do, what I do when I do it, and choose a time where it’s going to have the least amount of impact on my family.

I remember early in my business where I had to work seven days a week and it was not a choice, and it was awful for everyone. So that transition is so fantastic.

Lindsay Halsey:

It has been huge, and I’ve also found that when I define the block of time, I don’t stress. So, if it’s Sunday afternoon, like this weekend at 3:30, we’re picking up our kids and we’re going camping and we’re coming back late Saturday night. So quick trip. And on Sunday, we’ve got some birthday parties and things, but I already have from two to five on Sunday as me, I’m at the office time.

And so, I just sort of can relax with my whole weekend, knowing that’s coming and knowing that I’ll get plenty caught up in that little time period that I blocked off. Whereas the old way I used to do it, would have been like, “Ooh, I don’t know if I can go on the camping trip. And I’m going to work a little extra on Friday.”

If I make the choice to work on a weekend, it’s usually just that very concise time, and it feels totally different than that same three hours stretched across each.

Jennifer Bourn:

And is it scheduled and color-coded in your calendar?

Lindsay Halsey:

Yes. And it goes on the personal calendar because usually, it’s me taking time out of my personal life.

Jennifer Bourn:

And that is really powerful to say, “I know it’s going to be there. I’ve scheduled that time so I can relax because I know I have that.” Because I feel like when you don’t have time scheduled and everything’s just fly by the seat of your pants, I’ll get to it when I get to it, there’s this sense of dread that maybe you won’t have enough time and that’s a really terrible place to be.

Now you mentioned that you’re going on your first no email vacation in a really long time.

Lindsay Halsey:

So, no-email vacations were the norm for me when I had an agency and I have a business partner and we had a very defined body of work. It was just the two of us and I could get my work done in advance, pass the baton to Lori, and she would do that. And we could exchange that favor for each other a couple of times a year.

But that is as our team has grown as our lives have gotten more complicated and our business lives, the no email vacation has been totally out of the picture.

Jennifer Bourn:

It feels so hard.

Lindsay Halsey:

It feels so hard and then it also feels so worth it. And I know I need it and it’s healthy and it’s healthy for our team. It’s good for everybody and today was actually my first day and that is, I am examining everything that I do. And making sure that there’s a way for somebody else to do it. And so, I’m still a cog in the wheel that slows things down in certain processes that I don’t need to be part of.

And there are still lots of inefficiencies, of course. And just little things that someone else is going to need to pick up and do, and when I’m away. And I’m starting to build what that looks like for a team, because I can’t just say to one of our team members, “Go handle the support for the next two weeks,” because his response is, “I don’t know how to fix that in Stripe or I don’t know this, and when this happens, what do I do?”

And so, it’s not fair of me to put that on and I’m not going to be able to sign off because instead of answering the customer’s email, I’ll just be answering his email.

That’s sort of my goal. I’m giving myself like a six-week runway and I’m trying to get all the documentation in place in a short period. So that May is our trial run and by June we have the systems in place. And I have a feeling everybody’s going to enjoy my time out of the office because it’s always nice. Sometimes when you just have your, playbook, you got your work and you’re doing your own thing.

Jennifer Bourn:

That’s a great perspective to take — of saying, “I want to have this done. I want to go on this vacation. I want to be able to shut down email and not open it.” But you didn’t wait till the last minute to get that done — taking time to say, let’s look at what’s might fall down if I stop answering email and start setting up those processes and have a trial run a month, I mean, the emotional wellbeing that will come with being able to shut off that email and feel good about it because you set everybody else up for success is just going to help you have an even better vacation.

Lindsay Halsey:

It’s been a long time since I’ve taken a sign-off email vacation. And so, knowing that this time it’s going to be a pretty heavy lift and heavy effort.

I do anticipate that if I want to take another week off in the fall, it’ll be turnkey because we’re not going to have new systems and new processes and things. We might have a new team member or something, but for the most part, if I can keep that momentum up, maybe I can get to a very healthy lifestyle, like three weeks a year where I sign off email and that’s really what we encourage our team to do.

And so, it’s sort of like following your own guidance. We ask our team members to take their vacation and when they do to totally sign off. And if we’re asking that of other people then I got it. I need to get there too.

Jennifer Bourn:

My no-email vacations are hands down the most fulfilling that I take because I truly get to recharge and not think about work and not get sucked into things. Because I don’t care what anybody says, you check your email and there’s that one thing in there that’s going to stay with you for days.

Lindsay Halsey:

Exactly or like right before bed, it seems innocent, to check your email and then something gets in your head and you start thinking about it from 10 angles, and all of a sudden, you don’t sleep as well. And that’s not a vacation.

Jennifer Bourn:

I have always had no problem telling my clients I’m going on vacation, I’m unavailable and you cannot reach me by email. Brian has had a way harder time doing that. This is just not in his nature to be able to do that. And when he made the transition from being a partner in my company and took a job and went to work somewhere else, it took a minute to realize, I’m not the boss anymore. And he still found himself checking everything because he had that owner’s mentality, checking everything, even when we’re gone. It took removing Slack, removing the email app, and removing all of those apps from his phone altogether before a vacation. So, when that flex came up, I got a check, you can’t.

Lindsay Halsey:

Yes, exactly. So, I think I’m going to do that, which is that’ll be the true test is when I remove the email app and then, be totally signed off. You know, these days we all use our phones for like navigating, especially when traveling and new places.

Text me if you need me and I’ll get back to you. Maybe that’ll happen once or twice, but nothing major, very different from that 15-minute email check.

Jennifer Bourn:

Oh, a hundred percent. So, I’ve got a question. You mentioned too many tools and successfully condensed those down into one. And are now using ClickUp.

What other tool have you discovered that you cannot live without?

Lindsay Halsey:

So this is a non-business tool and it pings on another challenging part of life, which is keeping everybody fed. Whether you’re a team of one, two, three, four, or more, food management is so time-consuming. When COVID came, I finally learned about Instacart and then like grocery shopping apps or using the Whole Foods app and just picking up your groceries.

And that for me has been literally my hands down favorite tool. The thing you won’t be able to delete from my phone on vacation because I’m going to use it to order our groceries for when we get delivered at home. It’s just saved a lot of time and taken away one of the things that I don’t really enjoy doing, which is grocery shopping,

Jennifer Bourn:

Okay. I think you might’ve just shared one of the biggest game-changing tips I’ve ever heard.

When we go on vacation, we say, “We eat down the house before we go — we need to eat everything in the refrigerator and the pantry before we go.” So, everything’s basically empty. And then we come home, and we have no food and we ended up eating out way too much because we haven’t gone grocery shopping.

Are you ordering your groceries for when you get back from vacation while you’re on vacation so you can just go pick them up?

Lindsay Halsey:

On the plane or whatever, I just jump on my phone. And yesterday I was out on a camping trip and yeah, I had the groceries sitting at our doorstep for the week. And yes. I mean, I do enjoy a little bit of grocery shopping from time to time.

But like everything, I want it to be on my time, like when I have the time and I can get some joy from it. But if it’s just oh, tomorrow the kids need a banana for their lunchbox, and they need this and we have nothing in the house that’s stressful to me.

Jennifer Bourn:

I pride myself on being a pretty good road trip planner/meal prepper across the board, but that is not something I have ever even considered — and the post-vacation groceries have been such a pain point! I’m going to try this next time we travel.

I’ve never ordered my groceries. Like our grocery store is two blocks away. So, it’s no big deal. I’ve never done this before. And that may be why I get a grocery app on my phone.

Lindsay Halsey:

It’s a good one for the vacation. And I can imagine, I mean, I have young children, I can’t leave them at home. So, for me, grocery shopping is a family activity most of the time. So, the kids and I grocery shopping is so expensive because they’re throwing stuff in the cart. I’m usually tired. Somebody usually melts down; it might be me. And now it’s become much easier.

Jennifer Bourn:

Well, I love that you recognize this isn’t a fun thing that we do together. As a family, we have a limited amount of time off and time together that we’re not working. So, let’s maximize that by doing the fun things. And let’s use a system, a process, an app, whatever, to take care of the things that we don’t like doing to.

Lindsay Halsey:

It’s working for us right now. Sometimes, you give it a go, you made sometimes find like, oh, whatever, wasn’t as fresh as you wanted it to be. But then I always take a step back and I’m like, but I didn’t have to do it. So we’re good.

Jennifer Bourn:

Nice. And what do you do to ensure that you have a great day or remain in a positive headspace? Because we might outline what our ideal day looks like, but it doesn’t always go to plan. How do you stay positive?

Lindsay Halsey:

So exercise for me is kind of the key because exercise leads to sleep and decreases stress and anxiety. Mostly my exercise is very fluid, so I’m not like a big scheduler of my exercise calendar. It’s more, oh, I have time for a quick run here. Even going just for a quick walk is a great way to clear my head in the middle of the day.

Even if I have 20 minutes it’s enough that at the end of the day, I don’t feel like I just sat in it at my desk and took care of kids and cook dinner and things like that. And then the other is the other kind of big thing at the end of the day is a really defined part of my day that I have for my family that’s not me cooking, cleaning, and doing laundry because a lot of times feel like I spend a lot of time with my family, but it’s not always focused.

The other things I’m trying to work in are just little small bits of my day. Today, my day is really busy, so instead of putting the kids on the bus, I drove them to school. I walked them in, I said, hi to their teachers, and then I came home. And that was my time to catch up with them, in the car, to connect with their world because the rest of the day is going to get away from me from a parenthood standpoint. Having that defined time with my kids and then also going a little beyond and including my husband and friends and things like that in, into that mix.

So that I, at the end of the day, can really have my work life, a little bit of fitness and personal time, and then time with the people I care about. That’s the ideal day, but a lot of times balance comes over the course of the week and not over the course of a day.

Jennifer Bourn:

Got it. Do you have one last piece of advice to share for folks who might be in a state of overwhelm right now? Maybe they have the same fragmented approach of too many different tools. Maybe it’s just juggling too many different things.

What would you say to someone who is trying to get their overwhelm under control?

Lindsay Halsey:

What I’m trying to do now more often is check in with myself more regularly. Check-in with yourself once the feeling of being really overwhelmed or the really high-level stress that we have kicks in. I’m trying to check in with myself more regularly and ask, “What’s going well and what’s not going well?”

And then thinking of it like a problem-solution framework from there. So, they don’t have to be big things. But I personally think if I can pick up on the littler things as we go, maybe I won’t hit some of these periods where I hit a level of overwhelm that makes me question the whole plan.

And yeah, what is going well, what isn’t, and just checking in with yourself on a regular basis. And if you can’t identify it, ask people on your team, what’s going well for them and what’s not because they might be in the same place.

Jennifer Bourn:

I love the idea of doing the more frequent little check-ins. Thank you so much for joining me and being willing to talk about some of the less pretty sides of business, the overwhelm, and all of that. It’s been really eye-opening to see some of the steps that you’ve taken to simplify your own workflow and empower your team, and also to do the same for your family.

Lindsay Halsey:

Thanks so much Jennifer.

Jennifer Bourn:

If you enjoyed this episode of seeking satisfaction, subscribe for new show updates at Jenniferbourn.com/seeking-satisfaction/ and please leave a review on your favorite podcasting platform.

If you would like to hear more from Lindsay and learn about how she thought through the consolidation of tools and systems to streamline workflows and how you can do the same, check out the Seeking Satisfaction Extra Minutes Membership.

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Until next time, may you live inspired, embrace imperfection, seek satisfaction, and have a fabulous day.

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