231 | Boss October For Pro Organizers

BusinessPodcastMarketing

Oct 13

Written By Melissa Klug

My client and friend introduced me to the concept of Boss October several years ago--and I loved it so much I make sure we do it every year. This year, we are going extra on it--and I'm talking about that and giving you practical ideas to go implement it for you as well.

This year, we are going extra on it--and I'm talking about that and giving you practical ideas to go implement it for you as well.

Listen on Apple Podcasts

Listen on Spotify Podcasts

You can listen right here by pressing play, or you can read the full transcript below!

LINKS FOR LISTENERS

Connect with Melissa and Pro Organizer Studio: CLICK HERE
If you are interested in our Inspired Organizer® program, you can find us at www.inspiredorganizer.com
We have a whole library of podcasts here, our YouTube channel, and you can find us on Facebook and Instagram at Pro Organizer Studio.

FULL TRANSCRIPT

Melissa:
Hey, pro organizers. It’s Melissa, and it’s Monday. We are almost halfway through October, which is crazy.

But we are doing something in our Inspired Organizer group that I would love to invite you to. It is called Boss October. We talked about it briefly on the last couple of podcasts, but the concept of Boss October came from an organizing client of mine—just a lovely, all-around good human being.

She spends the month of October doing tons of stuff that she has put off throughout the rest of the year.

You’ve seen those internet memes that say, “That thing that I put off for three months took me 10 minutes to do.” It’s like that, only on a bigger scale. I know there are a lot of things that many of us avoid—including me—and we’re trying to power through those things.

The original podcast is about personal stuff, and I’m attaching that because it really gives you the concept. And by the way, I am Boss October in my personal stuff too. One example is insurance—our homeowners and car and everything. It has gotten completely out of control. Our AT&T bill is another one that I’ll be looking at. So Boss October can translate for personal and professional.

In our Boss October group, we are really doing this to get our businesses up to where we need them to be.

So what we’re doing in our Inspired Organizer group is we are going through and giving you a live-coached version of our course. We are doing things every single week to walk you through all of our content, to really shore up our businesses, to get ready to go into 2026 strong.

And I would love for you to join us if you are interested at all.

Our Inspired Organizer program is closing at the end of the month—October 31st—because we are going to be making a ton of changes ourselves as we go into 2026.

If there are things that you have been afraid of implementing in your business, or you just don’t know what to do, or you are in analysis paralysis or comparison-itis, or any of those things, I would love to be able to offer you some help.

Stop putting the thing off. Let’s do the thing together. Take advantage of Boss October and take advantage of our course and community being open.

I’ll talk more about it in the upcoming days, but please hit up proorganizerstudio.com/links and all of the goodness will be there.

And by the way, this applies to people who’ve been in business for many years. All of us who’ve been in business for a long time have things that we need to clean up. And every single day, I look at businesses and I look at organizers and I say, “Let’s crisp this up, and this, and this.” And that is what we’re trying to do with a little bit of live coaching and community support.

So I would absolutely love to have you. Inspired Organizer closes on October 31st. And if you want to have a call with me to talk about what it looks like being in our programs, I would love to do that too. Just reach out to me at hello@proorganizerstudio.com, and I would love to chat with you.

Okay—so this is an encore episode, but it hasn’t been on for a long time. You haven’t heard it in three years. I would love for you to listen to my client Leah talk about Boss October, and I hope that this is a great kickoff for you—professionally, personally, all the things—and I would love to chat with you.

Talk to you soon. Have a great day, organizers.

Melissa:
Can you give me a little background on what Boss October is?

Leah:
Sure. Before the plague in 2020, I was on a girls’ 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 in the Peloton studio. I’d had the bike for five years, and I’m so thankful that I got to ride in the studio before there were no live classes and before New York City was not a place to visit.

So we had this wonderful weekend, and it was the end of September. And if you’re not a Peloton person—like I’m not a religious Ally Love rider—but she 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.

So she would introduce a hard interval and she’d be like, “Hey, we’re going to do this and it’s going to suck. And it’s Boss October, so boss up.”

And so my aunt and I just started using the phrase “Boss October” because it’s catchy. But we didn’t really use it with regard to exercise—we 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 we put these things off, and they have more weight hanging over us than the effort it takes to just do them. There are little things every day, but then there are these bigger things that you just need to do.

So I started a Boss October list. 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. Hence Boss 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:
Which I love for so many reasons. And we’ll get into a little bit of the detail about what comprises Boss October for you.

But I love that you’re trying to do one thing a day, 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 today. Cool. I’m done.” They aren’t hard things. They’re just things that are weighing on us.

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 a pain.

I remember one of your examples was you renegotiate some of your bills, like your cable bill. If you threaten to leave, then they reduce your bill by 50%.

You look at your expenditures. What are some of the things that comprise Boss October for you?

Leah:
One thing is insurance. And I may separate out like the insurances. I double check to make sure I have life, disability, and that I’m not totally overpaying for car insurance—just so I have a sense of what that costs.

And that usually takes a couple of days. I hate doing it. I hate making phone calls to people in the insurance world. I hate double checking or looking at the forms. But it just needs to be done, and it 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 because I did it last year. I think most of us probably put that off for years and years on end.

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 can’t be six hours of work. It has to be something you can do in 30 minutes that’s going to give you momentum.

So insurance is one of the things I try to do once a year.

And like you said—cable. Or look at your bill and see what’s on there. These are things I avoid doing, but they don’t take that long, and they might save you a boatload of money.

Also looking for hidden things you’re paying for. Like, I have a group text, and we have one member we get on her for something we call passive spending. She spends money on things and then forgets to cancel them.

And those things really add up. Looking for passive spending, looking for things you’re paying for—you probably save yourself a lot of money in this process.

I don’t know if you ever quantified it, but it probably has four digits if you do it right.

Melissa:
Yeah.

Leah:
Yeah. I think one year I saved four digits just on car insurance. When I bundled car and life and took something off, it was like, there’s a thousand bucks.

And some of these things too—they may not be pleasant to think about. Life insurance is a depressing thing to think about.

Another one is doing your will. That is such a bummer, but I’ve had a couple personal experiences with friends where a will didn’t exist, and it is a major situation.

No one wants to think about dying, but please make this part of your Boss October, especially since 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 a will.

And while we’re talking about death, because I’m passionate about this subject: maybe one job could be asking your parents what their code status is. “Okay, Mom, you’re 80—do you want to go on a ventilator?”

Maybe the job for the day is literally having a hard conversation you’ve been putting off. That hangs over you. Maybe it’s not code status, but figure out what those things are that have weight.

And they aren’t hard. This isn’t like “I’m going to clean out all my closets.” These are things that may be as simple as a two-line email so that you can just start it. It doesn’t have to get finished either. Sometimes it’s in the starting.

Melissa:
Yeah. And all of these things are super important, yet super easy to put off. It’s very easy to go, “I’ll do that another day.”

So Boss October is the idea that this is your month where you just say, “I’m going to rip the Band-Aid off. I’m going to get it done.”

For the people in our audience too who are business owners, I want to talk about: how do you use this in your business?

Boss October can mean: What are the things I’m spending on in my business that I might not need to spend money on?

Or check your business insurance.

It could also be: What’s the status of my email list? Do I have a schedule for my social media and 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 to your business life.

Leah:
Totally. Here’s an example that would be a good business one.

Last year, one of the hard things I did during Boss October was I had a conversation with my cleaning lady about what a crappy job she was doing. She ended up getting passive aggressive, and by February, I had to fire her.

But it needed to happen. And now I have a really low-maintenance cleaning person that I pay a little bit more, but there’s no drama, and my house gets cleaned every couple of weeks.

That person had become an energy suck. And so I needed to address it.

So maybe as a business owner it’s like that: you have to fire someone, or fire a client, or there’s just this thing that isn’t right and is draining you. And it means a hard conversation. And that’s where you need to be.

And if you compress all those hard conversations into one period of time, there’s a finite end to it, right?

You can say, “Great, I’ve been putting this off for really long. I have to do it.”

Melissa:
One of the things that we talk about in our Inspired Organizer group a lot is the concept of boundaries. So what you’re discussing is a boundary.

You’re resentful of that person. She’s taking advantage of you. And so you have to set a boundary: “Hey, I’m getting a service. It’s not being provided to me. I need to have that conversation.”

And it didn’t go well, so you figured out: this is not the person for me.

Leah:
Totally.

And I’m an ER doctor. I had a mentor many years ago, and 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 because the patient is hostile, or you have to have a hard conversation, or that nurse isn’t doing what she should be doing—whatever reason you don’t want to be in that room is the reason you need to be in the room.

And I think that’s what Boss October is. It’s like: the things you don’t want to do are the things you probably need to do.

Melissa:
Every time we have a podcast guest, there’s that record-screech moment of something they say that is super good. And that one is it: The room you don’t want to be in is the room you need to be in.

Because these are all things that may be unpleasant, but they’re weighing on you and bothering your brain more than you realize.

Getting them off the list—getting them done—there is a huge freedom in that.

Do you have a favorite Boss October thing? Something where you’re like, “This alone was worth the price of admission.”

Leah:
I like easy things, because I’m easy.

One of the items is always: get out your vitamin D and recognize that winter is coming.

So literally, I put the vitamin D in my bathroom so that I’m not horribly seasonally depressed in February.

It’s super easy, but it needs to happen. And it reminds me that I need self-care in the winter so it doesn’t become this horrible, dark, long indoor slog.

And I try to figure out my Christmas card in my head at least—so that it’s not December 1st and I don’t have one.

It takes a while to get my kids and husband in real clothes, so it needs to start in October.

I also start holiday shopping or at least a holiday list. It’s not that I’m a huge overachiever with the holidays, but I don’t like being behind because then it becomes a chore and not a joy.

Melissa:
It’s exhausting. It’s another thing that hangs over your head.

And sorry if vitamin D isn’t relevant to you, but in Minnesota—it’s a thing.

Leah:
Okay, this is a Peloton reference. How do you know somebody has a Peloton? They talk about it constantly.

I need to get a bike fit. There are these people that Zoom with you and watch you ride, which sounds awkward, but if my settings are wrong, every time I’m on the bike it’s uncomfortable.

I’ve literally been meaning to do a bike fit for nine months. Boss October is not “work out every day.” It’s “schedule the bike fit you’ve been meaning to schedule for eight months.”

It will pay for itself and improve your life. You just need to do it and get over the fact that you hate being on camera with a stranger.

Melissa:
That reminds me: with clients, if they’re struggling to get through something hard, I always ask, “What’s your end goal?”

Your goal is to walk into this room without breaking your leg. We’re going to get to that. We have to go through a little mess to get there.

That’s the point of Boss October too. The end point feels so good, even if there’s temporary pain.

Leah:
For sure. And I have one email I’ve been meaning to send for eight months. It involves a spreadsheet, organization, and an email to everyone.

We all have one email we’ve been putting off. If you’re listening today and you have your one email—send it today. This is your sign.

And another example—low-hanging fruit:

I’ve been thinking about opioid overdoses. I’m an emergency room doctor. I have to prescribe opioids. People get addicted. People die.

So it’s been hanging over me: how do I communicate this risk clearly?

So I sat down and wrote something at a sixth-grade level—where you want discharge instructions.

It said: everyone can become addicted, and most people who become addicted start with prescription drugs. Therefore, I’m pleading with you as my patient to use the minimum amount for the shortest amount of time possible, and then get rid of them safely.

It took me 20 minutes. Sometimes it’s that simple.

And Boss October is for me—things intermingle. If you’re not taking vitamin D, you’re not functioning well at work either.

Home and work are intertwined, and health and work are intertwined—especially for professional organizers because the work is physically and emotionally draining.

So maybe the Boss October thing is: “My job is physically demanding. I shouldn’t be working six days a week with clients.”

Maybe you decide you only work four days—and then you build the schedule underneath it.

It’s the big picture and then doing the things underneath that you’ve put off.

Melissa:
Yeah, your job is really hard. Your people do really hard work.

And Leah has said to me that she would rather resuscitate a dead human than declutter something.

Leah:
I did say that. That is true.

Melissa:
Which is why we work together. We all have our strengths.

And it makes you better at work to have an approach to things at home—to clear your space and clear your mind. That’s what we help people do.

And that’s one of the reasons I wanted to talk to you today: Boss October is not only for the people who listen to this podcast, but it’s an extremely powerful tool organizers can take to their clients too.

It’s a great concept to help clients make forward progress so they can live a better life too.

Leah:
Yes.

And I should clarify something: be careful with your spouse when you talk about Boss October because they may misinterpret it as “I’m the boss of you.”

October is about being the boss of yourself. Like I tell my kids: mind your own bobber. Pay attention to your own fishing line.

Boss October is about minding your own clutter and your own list.

Boss October 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.

Because you can’t. If you let it slip that you’re doing Boss October and then you tell them to do something, they’ll be like, “Boss October,” in a passive aggressive way.

So you gotta have some rules around who you boss.

And for me, the rule is: I boss myself in October.

Melissa:
I love that. In the same way I tell clients we cannot organize someone else’s space. We cannot throw away someone else’s things.

Also, two of my favorite things about working with Leah: I learn something from every single client.

One, I learned how valuable Legos are. Leah’s family are huge Lego people, and it’s her fault now that I enjoy doing Legos as a grown adult.

I’m finishing the Seinfeld apartment right now. It’s my new favorite calming thing.

But I remember moving boxes at her house and she was like, “Be really careful— that one’s worth like a thousand dollars.” I had no idea. Retired Lego sets are valuable.

And the other thing: the value of keeping truly sentimental items.

Leah had a letter from a patient buried in paperwork that thanked her for saving his life. He was a young person in college, and it was heartfelt, and she kept it.

It’s important to uncover those beautiful things in our life—and that’s what decluttering does.

Leah:
Totally.

Melissa:
I’m so happy you taught us about this. I think you’re going to help a ton of people. I’m so excited you’re my friend and my client, and I’m so excited you shared with my audience. Thank you.

Leah:
You’re welcome. Thanks for having me.

Melissa:
Thank you to my friend and client Leah. I actually texted her the other day saying that I was revisiting Boss October, and she’s very happy.

And I would love for you to join us in our group. Please go to proorganizerstudio.com/links.

Also, while you’re there, if you have missed our last couple sets of podcasts, they have been wrap-up from the How To Summit. If you were not able to go to the How To Summit, they give you a little flavor of the learning that was done there. So we brought a little bit of the How To Summit to you.

And also, if you were there and want a refresh of what I chatted about, it’s there too.

Later this week—stay tuned for more stuff. That’s all I’m gonna say.

Have a great week.