be social



productivity hacks

Episode 91: “Boss October”–Productivity Hack for Organizers + Clients

Oct 13

We all have those things we put off–but what if you held yourself accountable to doing all the things you don’t love in ONE month? Our guest today has a productivity hack that we LOVE and want to share–and that will help you in your organizing business, your personal life, and that you can take to your clients.

“Boss October” will help you get important, yet easy to neglect items, done and off your plate so you can go accomplish the bigger things.

Our guest today is a client of our co-host Melissa Klug’s organizing business, Home By Eleven, in Minnesota. She is a physician and mom and wife and we are so happy she was able to join us to tell us about this great organizing productivity hack!

Links for listeners:

Information about our Inspired Organizer® program

If you are looking for business inspiration, we have a free workshop that is called The 4-Part Plan for Landing Your Dream Clients in 2021. Jen Obermeier leads you through that workshop. Sign up for that If you are interested in our Inspired Organizer® program, you can find us at


Are you subscribed to my podcast? If not, I want to encourage you to do that if you don’t want to miss an episode. Click here to subscribe to the podcast!

Now if you’re really feeling like spreading the love, we would be so grateful if you left a review on iTunes too. Reviews help us get found + we love getting the feedback. Just click here to review!

Join our free Facebook group for podcast insiders to get notified about new episodes (plus get behind-the-scenes access and other goodies weekly)!

If you are looking for business inspiration, we have a brand new free workshop that is called The 4-Part Plan for Landing Your Dream Clients in 2021. Jen Obermeier leads you through that workshop. Sign up for that If you are interested in our Inspired Organizer® program, you can find us at and don’t forget, we have a whole library of podcasts here, our YouTube channel, and  you can find us on Facebook and Instagram at Pro Organizer Studio.

Still not sure about starting your own Pro Organizing business? Cick here to read about the 5 things you need to know BEFORE starting your organizing business.

Feeling ready to start? Great! Check out this post on how to start your business stress-free!


Hey pro organizers! It is your podcast co-host Melissa Klug and I am really, really thrilled to be bringing you today’s guest because she is a client in my organizing business. 

The reason I wanted her on the podcast is because this is one of those great examples of sometimes our clients teach us things while we’re supposed to be teaching them things. And Leah taught me about a concept that she has called “Boss October.” She taught it to me last year in November, and so I have waited almost an entire year to be able to bring this to our awesome pro organizing audience, but she has some absolutely great ideas on how you can use this concept of Boss October, not only for your own business, but more importantly, how you can take it to your clients.

I love this concept. I’m completely obsessed with it. While the concept is Boss October, I will say, I know that we’re a little ways into October already. So the great news is you can call it Boss November if you want to, you can call it Boss December. You can do whatever you want.

But the concept itself, I think, is really, really powerful. Leah is an emergency room physician. She is a mom of three kids. She has a husband who is a teacher, so he has a very busy life. They have three goats, which is another one of my favorite things about her. She has these cool goats. She has a dog. She has a crazy, crazy busy life, but I am so appreciative that she took time out to teach us about this really awesome concepts that I think is going to help you in your businesses and also help your clients. Stay tuned to the end because we have podcast extras for you, including some lists and other stuff that you can use with your clients. So let’s get going with my client, Dr. Leah.

You’re listening to the pro organizer studio podcast with Melissa Klug and Jen Obermeier. Thank you so much for joining in our mission to broaden the horizons of savvy businesswomen in the organizing industry by instilling confidence and inspiring authenticity. You’ll gain new insight into strategies designed specifically for professional organizers.

So now let’s get started.

Melissa Klug: We are back on the Pro Organizer Studio Podcast, and I am excited because my guest is not only a friend of mine she is a client, so she can talk about what it is like to actually work with me.

And he has introduced me to several concepts. So when I was working with her, she introduced me to something that podcast listeners, if you have watched our YouTube will know. Is the concept of my cloffice. I now have a desk in my closet which was introduced to me by Leah. And another concept that we’re going to talk about in a minute.

So Leah, welcome to the podcast. Thank you for being with us. Last year. You and I were doing some digital work together. So cleaning up digital lives, and you introduced me to this concept of boss October, and I loved it so much.

I thought about it and I said, we have to do this this year. So can you give me a little background on what Boss October is? 

Leah: Sure. So, before the plague in 2020, I was on a girl’s weekend with my aunt to New York city. And one of the reasons I was convinced to go to New York city was to ride in studio.

And the Peloton studio, I had a bike for like five years. And I’m so thankful that I got to ride the studio before there was no live classes. And before in New York city was not a place to visit. So we had this wonderful weekend. It was the end of September. And Allie Love gave a live ride and introduced this concept of Boss October, which for her was this idea that you could just do anything in October.

Right. So like she would introduce a hard interval and she’d be like, and we’re going to do this and it’s going to suck. And it’s Boss October so boss up, you know? And so my aunt and I had just liked using this phrase, Boss October, cause it’s kind of catchy but we didn’t really use it with regard to exercise or used it with regard to our lives and all the things in our lives that are basically short sucky things that just need to get done.

And I think in life, you put these things off and, they have more weight hanging over us than the effort it takes to just do them. There’s little things every day, but then there’s these big things that you need to just do. And so I started a boss october lists, and I have a list of things that I don’t like doing that aren’t particularly complicated or long but just need to get done and.

Living in Minnesota. There’s no better time than to do it before you hibernate. So hence last October and a bunch of things I don’t want to do, but I try to do one thing every day or at least 31 things in October.

Melissa Klug: Which I love because, well, I love this for so many reasons and we’ll get into a little bit of the detail about what comprises to you, Boss October.

But I love that you’re trying to do one thing. And because there are actually all of these things that start building up. And I saw something recently that said that thing that I put off for three months took me 15 minutes to do so there are days where you’re like, Hey, my thing only took me 10 minutes a day.

Cool. I’m done for the whole day. They aren’t hard things. They’re just things that are weighing on us. Totally, totally so what I loved about yours is that you were explaining to me that you do all these things that you know are smart, but are kind of a pain. Like I remember one of your examples was you renegotiate some of your bills.

Like you renegotiate your cable bill, you know, like if you threatened to leave them, then they reduce yourbill by 50%,  you look at all of, your expenditures. What are some of the things that comprise boss October? 

Leah: Right. Right. So, well, one thing is I look at insurance and that is just, I may separate out the insurances.

So, I double check to make sure I have life disability and then I’m not totally overpaying for car insurance. And just so that I have a sense of what that costs and. And that usually takes a couple of days. I hate doing it. I hate making phone calls to people in insurance, worlds.

I hate like double checking or looking at the forms, but it’s like, it just needs to be done. And, and this sort of hangs over you, do I have the right policies? Do I have the right, person named as my beneficiary? And actually it was really easy this year. Cause I didn’t last year, I think most of us probably.

Put that off for years and years on end detriment. But you know, so it could be like, if your insurance is pretty good, you could do it all in one day. But if you have something super hard, like car insurance is super hard for you or life insurance is super hard for you. The job might literally be, Find three life insurance companies.

 That might be the job because it might just, it can’t be like six hours of work. So it has to be something that you can do in 30 minutes. That’s going to give you momentum. So insurance was one of the things that I try to do once a year. And like you said, cable or. Cell phone, like look at your bill and see what’s on there.

This is, these are things I avoid doing, but they don’t take that long and they might save you a boatload of money.

Melissa Klug: Well, and also looking for hidden things you’re paying for. Like, I have a group text that there’s one member that we kind of get on for something that we call passive spending really add up and working for all those passive spending things, because I suspect that you probably save yourself a lot of money in this process. Have you ever quantified it? But it probably has four zeros if you do it right.

Yeah. Yeah. 

Leah: I mean, I think one year I saved four zeros just on car insurance. Like yeah. Like when I bundled like car in life and took something off, it was like, there’s a thousand bucks, you know? So [00:08:00] did I say four zeros, four digits, 

Melissa Klug: four zeros would 

Leah: be zeros on something that would be amazing. 

Melissa Klug: I think I started, I think it’s my fault.

I think I started with four zeros, but, 

Leah: We meant four digits. 

Melissa Klug: Some of these things too, are they may not be pleasant to think about like life insurance is kind of a depressing thing to think about. And another one is doing your will, which is such a bummer. I also have had a couple of personal experiences lately with friends where a will didn’t exist.

And it is a major, major situation. No one wants to think about dying, but like, please make this part of your boss October, especially we’re talking to business owners, you own your own business. You have to have some sort of a financial plan and a backup via. 

Leah: Totally. And while we’re talking about death, because I’m passionate about the subject, like also maybe just like one job to be like, ask my parents what their code status is, you know, like, okay mom, you’re 80.

 If you get COVID you want to go on a ventilator, like maybe the job for the day is literally having a hard conversation that you’ve been putting. For a long time. And that hangs over you, that you worry about, maybe it’s not code status. You know, but figure out what those things that have weighed are that aren’t hard.

 This isn’t like I’m going to clean out all my closets, this is, and I think, we’ve covered that, but these are things that may be as simple as like a two line email, you know? So that you can just start it, it doesn’t have to get finished either. It’s like sometimes it’s in the starting as you know, I’m sure.

Melissa Klug: Yeah. And so all of these things are super important yet. Super easy to put off. It’s very easy to go. Like I’ll do that another day. I’ll do that another month. I’ll do it. And so boss, October, the idea is this is your month that you just say, I’m going to rip the bandaid off. I’m going to get it done. And.

For the people in our audience too, who are business owners. The concept that I want to talk to you guys about is how do you use this in your business? So [00:10:00] you can use boss October to say, Hey, not only what are the things I’m spending on in my business that I might not need to spend money on, or we all have business insurance check out your business insurance.

It could also be. What’s the status of my email list. Do I have a schedule for, you know, my social media, my email posting, I’m going to give you guys some ideas, but this concept can transcend beyond your personal life too. It can transfer your business. Totally. 

Leah: Oh, here’s an example.

That would be like a good business one. So last year, one of the hard things I did during the last October is I had a conversation with my cleaning lady about the job she was doing. And she ended up like getting really like passive aggressive. And by February, I had to fire her. But it needed to happen.

Right. And now I have a really low maintenance cleaning person that I pay a little bit more, but there’s no drama and there’s no way to this. Like my house getting cleaned every couple of weeks. But that person had become an energy suck. And so I needed to address it, you know, and so maybe as a business owner, it’s that you have to fire someone or that you have to fire.

Or that you have to, there’s just this thing, you know, that, that is it right? That is like draining you and it means a hard conversation. And so that’s where you need to be that. 

Melissa Klug: And if you compress all those hard conversations into one period of time, there’s a finite, there’s an entry, right? Like you can say great, I’ve been putting this off, or really I’ve been putting off this bad conversation for a while.

I have to do it. And yeah. One of the things that we talk about in our private inspired organizer group a lot is the concept of boundaries. So what you’re also discussing as a boundary, you’re resentful that person she’s kind of taking advantage of you. And so I have to set a boundary of Hey, I’m, I’m getting a service.

It’s not being provided to me. I need to have that conversation. And it didn’t go, well, they, you figured out, oh, this is not the person for me. So 

Leah: totally. And I I’m an ER doctor. So. I mean, that’s what I do. But I had a mentor many years ago who his mantra was, the room that you don’t want to be in is the room you need to be in.

And that might be, cause the patient [00:12:00] is hostile or you have to have a hard conversation or that nurse isn’t doing what she should be doing or whatever reason you don’t want to be in that room is the reason you need to be in the room. And I think. I think that’s sort of what box October is. The things you don’t want to do or the things you probably need to do, you know? Well, every time 

Melissa Klug: I’ve said this before, but every time we have a podcast guests, there’s like that record screech moment of something they say that is really super good. That one that’s your records for each moment of the room that you don’t want to be in as the room you need to be in, because these are all things that may be unpleasant, but it’s sort of like with our client, The clutter is bothering their brain more than they possibly understand.

These things are weighing on you more than, you know, and it is bothering your brain and getting them off the list, getting them done. There is a huge freedom in that. 

Leah: Absolutely. 

Melissa Klug: Do you have a favorite boss? October thing is there something that, where you’re like, ah, this alone is worth the price of admission?

Leah: So I like easy things cause I’m inherently lazy and one of the items is always get out your vitamin D. And recognize that winter is coming. And so I put the vitamin D on my bathroom so that I don’t, I’m not like horribly seasonally depressed in February and it’s like super easy, but it needs to happen.

And I need to recognize that needs to happen and respect the fact. I need to take care of myself. I think it, it, it also is like a self care thing for winter here. I mean, not all of your are wintering in Minnesota, but it is something so simple in my personal life that it reminds me that okay.

To do self care in the winter so that it doesn’t just, become this like horrible, dark long indoor. 

Melissa Klug: Yeah. It’s really something to live in Minnesota. You guys, I know a lot of, a lot of our listeners are in areas where this is not a situation that they have to manage, but here is a situation. So sorry if vitamin D isn’t totally relevant to you, 

Leah: but it is [00:14:00] like the easiest thing on my boss, active realist.

And it has to happen in October. The other thing is I try to figure out my Christmas card in my head, at least so it’s not just like, oh God, it’s like December 1st. I don’t have a Christmas card. You know, it takes a while to get my kids and husband and like real close. Start in October and we do a Christmas card every year.

Not everybody does that. Not everyone does Christmas, but it’s something we do. I generally start holiday shopping too, or start at least the holiday list. Cause it just, if it’s off my head and I’m early, to the game, I just, it doesn’t add stress. It’s not that I am a real overachiever when it comes to the holidays, but I don’t like be behind with the holidays.

Cause then it becomes a chore and not a joy or it’s 

Melissa Klug: exhausting. Right? Also, just from a totally tactical standpoint in 2021 supply chain problems, every industry are extremely real. Like any of us who have tried to shop at the container store in the last few months.

Now you can’t find beds. You can’t find baskets that is transferring to every industry. So holiday shopping early. Very smart this year. 

Leah: Yes. Yes. So those are some of my, like, things that make sense for October that I like, because I just, I feel like I’m ahead. Some of the other things, okay, this is a Peloton reference.

God, this, how do you know somebody has a Peloton? And they talk about it constantly. I I need to get a bike fit. So like I’ve been needing there’s these people that like zoo, I hate cameras, which is why it took like six days for us to coordinate this interview. But I also pay cameras. And so part of the bike that is you have to zoom in with someone and they like, watch you ride the bike, which sounds really awkward.

But think about it. If my settings are wrong, every time I’m on the bike, Writing in the wrong position. And so I’ve literally been meaning to do a bike fit for nine months and I have yet to schedule it, but it will happen in October because it’s on my list. Boss October, isn’t workout every day.

It’s schedule the bike fit that you’ve been meaning to schedule for eight months that will pay for itself and improve your life and improve everything. You just need to do it and get over the fact that you. Being on a camera with a [00:16:00] stranger, not, you’re not a stranger. No, that you would be a stranger, 

Melissa Klug: But your point, something that you said there reminded me of a lot of times when I’m working with a client, if they’re struggling to get through something that’s really hard. I always try to say, what’s your end goal?

You know, like your goal is to have this room that you can walk into without breaking your leg, that we’re going to get to that we have to go through a little bit of mess to get there. And that’s, to me, the point of boss, October two is, Hey, the end point of what I’m going to get feels so good. I’m going to have a little bit of temporary pain.

I’m going to have to be on with a stranger on zoom, but it’s actually gonna make my. Better. It’s going to prevent injury. It’s going to increase comfort. There are some end goals there that are good for you to achieve, even though you don’t really want to do it. For sure. 

Leah: I have one email that I’ve been meaning to send for also eight months, which is to my entire group about this like sabbatical issue where it involves a spreadsheet and a lot of organization and an email to everyone.

I just don’t like, it’s also on the list, like one single email that I’ve been putting off, you know, we all, we all have one email we’ve been putting all of us, 

Melissa Klug: every person I know has that one email. So maybe that’s what if you’re listening to this today and you have your one email, whatever that looks like, send it today.

This is your sign. Just be done with it, for 

Leah: sure. For sure. Or low hanging fruit, like, I think a lot about opioid overdoses. So there there’s like a, I’m an emergency room doctor. I have to prescribe opioids. People get addicted to opioids, people die of opioid overdoses.

Right. It’s just been hanging over me. I have conversations with people, but how do I communicate that clearly, that this is a true risk. So I sat down and I wrote something that says like everyone can become addicted and like most people who become addicted start out with prescription drugs.

Therefore I’m asking you, I’m, I’m pleading with you as my patient. Only use the opioids in the minimum amount that you need for the shortest amount of time possible. 

 I wrote [00:18:00] this and it’s like, ah, yeah, it took me like 20 minutes and. I sent it to a friend and she’s like, that’s amazing. Why are we all not writing this on our discharge papers? Sometimes it’s just so simple, but there’s momentum in, dang, I just wrote the thing I needed to write that I need to say.

And so there’s work things. There’s start vitamin D like the other thing about Boston tubers, this list is for me, I know you’re talking to people in their professional lives, but for me, it’s like those things intermingle, right? So look at me. If you’re not taking your vitamin D you’re also not maybe functioning at work super well. 

Melissa Klug: Well and health. And so health and work, especially intertwined for professional organizers, because our work is very physically draining.

It’s also emotionally draining and it obviously in a much different way than your work is physically and emotionally draining. But there may be some health things I need to take care of. You know, I haven’t taken a vitamin and three. It’s time to start a vitamin regimen or, I need to say, Hey, my job is physically demanding, so I need to make sure I’m not working six days a week with clients.

Maybe you say, I need to only work four days a week with clients. And then what does that look like in my schedule? How do I schedule people? It’s thinking about all those big picture things and then doing the things that are underneath that, that you’ve probably put off for a while. Yeah, 

Leah: your job is really hard.

Your people do really hard work. So, I mean, I’ve said to you that I would rather resuscitate a dead human the declutter or something. That is the truth, which is why we work together. Because we all have our strengths. Right. And, that might sound really callous, but the point is that’s my job.

 If that’s what comes in, I have to do that. And I’m pretty good at it. And you’re pretty good at helping people to declutter. You’re actually excellent. But it makes me better at work to, have an approach to things at home and to be able to clear my mind and like you help people do that.

You help people clear their space, clear their mind. There is so much weight and that’s what foster is, right? It’s like this weight of the clutter of the things. And so like, your work is amazing. And keep doing it all. You have you, [00:20:00] all of you, people, 

Melissa Klug: we do love doing it and people 

Leah: so, so much 

Melissa Klug: all kinds of people.

We do help people. And that’s actually, one of the reasons that I wanted to talk to you today is because boss, October to me is not only for the people that listen to this podcast, but it is an extremely powerful tool they can take to their clients. So people who struggle with having some of these things hanging over their heads, it’s just as great concept that we can take to our clients and make sure that they’re making the right forward progress so that they can live a better life, too.

It’s all, all we do is make sure people live better lives. Oh 

Leah: yes. And I should clarify something. When you said last October, it just reminded me of something. It’s a little bit of a job. Be careful with your spouse when you talk about last October misinterpreted as like I’m the boss of you. So cover is about being the boss of yourself.

And really, like I tell my kids, mines are a bobber, which in Minnesota is a fishing thing. Pay attention to your own fishing line. Right. I think boss October is about, minding your own clutter, minding your own list. And like Boston, silver does not involve telling my husband to, put the snow stakes in or clean out the garage or do the things I want him to do in October.

 So just, you know, you gotta have some rules around who the boss. And for me, the rule is that I’ve asked myself in October, I tell myself to do all the things I’ve been putting it off.

Melissa Klug: I love that in the same way that I tell my clients that no, we cannot. Organized someone else’s space. We cannot throw away someone else’s things. Yeah. That’s a very, very good point. Well, two of my favorite things about working with you, I mean, like there are a million, but two things. I always learn something from every single client.

Right. So one of the very important things I learned at Leah’s house is how valuable Lego’s on. Because her family is, are huge Lego people. They have actually it’s her fault. Now that I enjoy doing Legos as a grown human I’m just finishing the Seinfeld apartment right now. I love it. It’s my new favorite, [00:22:00] calming thing.

But I remember when I was at her house, we were moving things around and she’s like, Hey, be really careful with those boxes because that one’s worth like a thousand dollars. And I’m like, oh my gosh, I had no idea.

Yeah, that’s right. Retired Lego sets. I learned the value of those and how careful you have to be with them. And the other thing, the value of keeping truly sentimental items there. Leah is a physician. She had a letter from a patient that was buried in a bunch of paperwork that basically thanked her for saving his life.

He was a young person in college and it was this very heartfelt letter about how she really legitimately saved his life down the road. And she kept that letter. And I just remember thinking it’s important for us to be able to uncover all these beautiful things in our life. And that’s what decluttering does.

Totally totally. Well, I am so happy that you have taught us about this. I think you going to help a ton of people and we appreciate it. I’m so excited that you are my friend and my client, and I am so excited that you shared with my audience. So thank you. You’re welcome. 

Leah: Thanks for having me. 

Melissa Klug: I hope you enjoyed my conversation with Leah as much as I did. I wish you guys were able to know her in person because she is awesome.

And I am really grateful that she brought this concept into my life and into yours. Like I said, I really think this is an incredibly powerful tool for all of us in the organizing industry, but also it’s something that you can absolutely take to your clients. So with that in mind, we have created some extras for you from this episode and they are going to live at our website.

At the podcast episode link. If you go to pro organizer, and click on this episode, you are going to find so many goodies there. You are going to find checklists for your own business and for your clients, you can find an edition of this podcast that is. Specifically for clients.

I took out some of the references to professional [00:24:00] organizers specifically, but it’s something that you can use with your clients and direct them to that. 

 We coach professional organizing clients every single day at pro organizer studio and in our inspired organizer course. And what a lot of people struggle with is the stuff that kind of hangs over your head. And look, we all do it. I do it. Jen does it. We all have these things that hang over.

So if you can do it for yourself and create that commitment to get those things taken care of. And if you can inspire that in your clients as well, you are going to really make this fall. Absolutely awesome. I was so excited to bring this concept to you. If you guys have any questions at all, I always answer emails at or you can hit us up on Instagram at pro organizer studio.

Have a great day.

Thank you so much for listening into the Pro Organizer Studio Podcast. If you’d like to get our roadmap for success as a pro organizer, head straight to

That is all that we have for you today on this episode of the Pro Organizer Studio podcast, if you have not yet joined Jen Obermeier for our free workshop, your four-part plan for landing your dream clients in 2021, hop over to and we will get you that workshop on demand. It’s a great way to spend an hour of your time.

Thank you so much for listening in to the pro organizer studio podcast. If you’d like to get our roadmap for success as a pro organizer, head straight to

comments +



Photos of jen by ANGELA ZION