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Jessica Litman of The Organized Mama: From Avocation To Vocation; How I Turned My Hobby Into A Career

An Interview With Jason Hartman

Not every project is meant for you, but it can show you what is possible. I have had many opportunities come into my inbox that have not come to fruition. It can be super discouraging, but I have learned that it is just an opportunity to show you what is possible. About 5 years ago, I was asked to write an article for Domino magazine. I wrote the article. They said they loved it. And I waited patiently for it to be published. After a month, I followed up to see when that article would be written and I was told they passed on it. The same thing happened, just a few days ago, with an opportunity to be on a national morning show that ended up not happening. But those opportunities have shown me what is possible for my career.

As a part of our series about entrepreneurs who transformed something they did for fun into a full-time career, I had the pleasure of interviewing Jessica Litman.

Jessica Litman is the founder and CEO of The Organized Mama. Over the past 8 years, she has taken her talent and eye for all things organization, home decor and DIY and built a national name for herself. Using her knowledge and extensive experience in her field, Jessica also provides a business consulting service to help others succeed at launching their own businesses.

Thank you so much for doing this with us! Can you tell us a bit about your “childhood backstory”?

I have always been an organized person. When I was five years old, my parents said I would line up my stuffed animals on my bed before I would go to sleep. I didn’t realize what a chore was until I was in middle school because I did all the typical chores like make my bed and clean my room without being asked to do so. I witnessed a friend pass away in middle school, which led me to finding the need to create order in my bedroom as a way to cope with the tragedy. So, I taught myself tricks to keep more things organized like flipping hangers around to see if you actually wear the clothing in your closet, folding techniques, and decorating and styling of shelves with minimal things. When I was in high school, I searched the internet for organizing and came across the National Association of Professional Organizers (NAPO) and thought that would be a fun job. It wasn’t really a thing at the time and my parents said I would make no money being an organizer. So, I decided to go to college to be a teacher. In college, I lived with a bunch of girls. And they would always try to move things around my room to see if I would notice. And I always noticed. It was helpful because I would know if someone went through my closet and took my clothing. While I was teaching, I was always told by other teachers how organized my room was. I was sick one day and had another teacher pull materials. She was so impressed when I told her the exact drawers and cabinets everything was in. I went on to get my master’s in special education and became an inclusion specialist. So, I would make home visits to my families. During that time in their homes, I would help some families organize the paperwork that came with special education. I decided to stay home when my son was born, which led me to starting a blog about organizing.

What was the catalyst from transforming your hobby or something you love into a business? Can you share the story of your “ah ha” moment with us?

It started with writing a blog. Being home with an infant can be isolating. So, I decided to start writing a blog about organizing and decorating our house. Since most of my family lives in Minnesota, it was an easy way for them to see what we were doing to the house while giving me something to do during nap time. One day I had a bunch of mom friends over for a baby group get together and some of the moms were asking how I learned how to organize. I told them it was just something I knew. So, they asked for advice. And I helped them organize spaces in their homes during play dates. That led to organizing more people’s homes. And that was when I realized I could turn this into a business. When people who didn’t know me were reaching out because they read my blog or heard from a friend that I could help them.

There are no shortages of good ideas out there, but people seem to struggle in taking a good idea and translating it into an actual business. How did you overcome this challenge?

So, I always tell coaching clients to just start. I offer a business coaching service where I can support people with online or service-based businesses, organize their physical spaces or organize their business processes, which is what turning a good idea into a business idea truly is.

One thing I notice is that people get caught up on the execution. So, they don’t even start. You have to just try and put something out there. Because once you have something out there, you have a place that you can edit, tweak, adjust and change. But when you have nothing, you don’t have anything to start with.

When I started my blog, I didn’t tell anyone. I would write articles for myself. My friends found the blog after some time, but my writing got better because I had just started. But if I never started, my writing would have never gotten better. My storytelling wouldn’t be great. I might even be writing with 2 spaces in between sentences, instead of one (which is how you write for the Internet).

So just start with any idea because you will have something to fix once you have a place to start.

What advice would you give someone who has a hobby or pastime that they absolutely love but is reluctant to do it for a living?

Only if someone is willing to risk their love of the hobby would I recommend jumping in and doing it for a living. I live by the motto that not everything needs to be a business. I got this mindset from the book Big Magic. Elizabeth Gilbert talks about how your creativity doesn’t need to support you financially. That is just too much pressure to put on your gifts. And I completely agree with her.

For me, I love writing and teaching, I would do it even if I didn’t get paid. So, I am comfortable with not making money off of those skills. I am good at organizing and I know that can pay the bills, but I don’t always love doing organizing projects. So, I take my organizing and use that to pay the bills, so my writing and teaching don’t feel the constraint of paying the bills.

So, to anyone who wants to turn their hobby into a business, make sure you have other ways to inspire your creativity while also paying the bills. Then you will never run out of creative ideas. It is about balancing the two.

It’s said that the quickest way to take the fun out of doing something is to do it for a living. How do you keep from changing something you love into something you dread? How do you keep it fresh and enjoyable?

I think I answered that above! But I will also add that adding in an hour of “play time” for your hobby helps you stay engaged.

Each week, I spend an hour painting or drawing. I love painting and drawing, but I don’t do it for a living. It is something that I keep to myself. So, I suggest finding something that you keep just for you. This will allow you to enjoy the other aspects of what you do for a living.

And, if it gets boring, switch what you do. No one said you have to do the same thing for the rest of your life. Change what you are doing — outsource the things you dislike, invest in your education and training, find others in the same field, join groups that support what you are doing and attend conferences. And never feel like this is what you have to do for the rest of your life. It is your life. So, you pick what path you get to go.

What is it that you enjoy most about running your own business?

I enjoy the freedom I get in setting my own schedule. I can attend school events for my kids. I can take time off when they are off. I can drop them off and pick them up. I can take on projects I want to do. I can turn down projects I don’t want to do. I have total freedom to create things I enjoy and get excited to do.

What are the downsides of running your own business?

The stress of having everything on your shoulders. If you mess up, you feel the pressure to make up for things. And if you are on deadlines, you have to hold yourself accountable. No one else will.

Can you share what you did to overcome these drawbacks?

I try to outsource things I don’t like doing so I can focus on what I am good at. That gives me the confidence to run my business in a way that works for me. When I first started out, I was doing everything myself. But I would get so frustrated that I would just stop. So, I found a virtual assistant to help with silly tasks so I could stay focused on what I enjoyed doing. This helped me take the pressure off of some things so I could focus more on things I was good at, which gave me more confidence. Also, I would and still talk with other business owners through masterminds because they are going through the same things as me.

Can you share what was the most striking difference between your actual job and how you thought the job would be?

I really don’t know if there is a difference. Because I have designed my business to work for me, what I envisioned and what it is, is pretty much the same.

Has there ever been a moment when you thought to yourself “I can’t take it anymore, I’m going to get a “real” job? If so, how did you overcome it?

About every quarter I go through this, but I know it comes. So, I end up saying I should give up. Then, I go search on LinkedIn for an hour, reading job descriptions and getting annoyed that I can’t find something that looks interesting. Which is when I realize that I need to keep doing what I am doing. I have never been a person who likes someone else telling me what to do. In Gretchen Rubin’s book, The Four Tendencies, I am the “rebel.” So, as I read the job descriptions, I realize that all these jobs are dictated by someone else and I just give up and go back to doing what I enjoy. Sometimes, I end up giving my assistant different tasks to change up what I am doing and sometimes, I just need some time off. Other times, I get inspiration based on what I see online. So, I get to work on a new product or course.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

When I first started my blog, it wasn’t called The Organized Mama. It was called Coffee and Choas. I paid a girl on Etsy to create a logo for me and bought the domain, I couldn’t believe that the domain wasn’t taken. That might have been because I typed in “Choas”. So, the URL for my very first site was “coffeeandchoas.com” when I realized that I had to change it. And what do you know, coffee and chaos was taken.

So, I decided on The Organized Mama because my son would call me mama at the time. I learned that you need to spell check your stuff and not do things on your phone or iPad. So, I invested in a computer after that misstep. Now I question if how I am doing something is good enough or if there are ways I can improve so I don’t make mistakes, like misspelling a word or recording videos with crummy quality.

Who has inspired or continues to inspire you to be a great leader? Why?

Joanna Gaines inspires me as a leader. I heard her speak at a conference and what she said really resonated with me. She created her business to work with her family. She shared she doesn’t like to travel so companies come to her for meetings, which is my goal for creating my business. I want to be home with my kids, but still create a business that is as successful as Magnolia is for the Gaines’. She has amazing boundaries with being a public figure. I am inspired by that quality and how she balances that aspect of her life. She has been very honest with how her business has evolved. They started with a little shop that she closed to raise her kids. Then she started things up again when the kids were a bit older. I appreciate the honesty she has shared about that part of her business journey because most public figures don’t always share the not-so-great parts of starting their businesses.

How have you used your success to make the world a better place?

I truly believe that when your home is clutter-free you have more patience and are better emotionally regulated. When you are patient and have your emotions cared for because your home environment isn’t causing you stress, I feel that helps society as a whole. Since I have had some trauma in my life, I know how important that is on your mental health. When your life feels out of control, you need a place that you feel comfortable. Where you feel you can relax and aren’t on edge. Which is why I feel teaching others how to organize is how the world can be a better place. Focusing on mental health through organizing can help so many families.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

1. Not everyone is actually invested in your business. When I was about two years into writing my blog and a year into organizing people’s homes, I attended a conference. I found a few business owners who I thought were incredible. They were running coaching businesses that appeared to be knowledgeable. I listened to them speak and asked them questions about my business and what they think I should do next. They gave me advice that I took to heart. I thought that they were the smartest business people out there. Well, they weren’t. They were not invested in my business, they only wanted me as a customer. So, their advice was for me to hire them to do these things that they suggested. I learned after a failed attempt at a subscription video service I invested money into that they had no interest in supporting my business, but to increase revenue from theirs.

2. Not all advice is good advice. Similar to what happened above, I have learned that not all advice is good advice. A few years into my business, I decided to hire a coach to help with my business. I had “discovery calls” with so many. And thought I found a good one. She would give me advice and I would do what she said. And most of the time, I didn’t like what she suggested. It wasn’t something I was interested in. One thing she told me to do was to make physical products, so I made notepads. But I hated selling them. I hated getting negative reviews on Etsy because shipping took too long. And it made me get anxious. But she kept saying that that is what I needed to do. So, I listened and did it. But after a month of this, I realized I was losing money trying to ship these notepads out based on the advice she told me about selling products. I stopped selling them and moved onto things I enjoyed. I haven’t stopped listening to my gut ever since. So, if I am trying to decide if a project is worth it, I will stand up straight with my eyes closed. I will say over and over “yes” and see which way my body leans. Then I will do the same with the word “no”. After I have noted which way my body leans, I ask about the project. I will say a word over and over and see which way my body leans. And that is my cue for what I need to do.

3. Not all experts are actually experts. You know how many people claim to be experts? Well, I started to look into some of those claims. And some people who say they are an expert haven’t even had a business in that field they are claiming they are an expert in. If you haven’t run an online business, I can’t call you an expert. If you haven’t actually run a successful organizing business, I can’t call you an expert. I took an online course from a woman who claimed she was a successful blogger. I took her course and quickly realized that nothing in the course was new information. After talking with others who took her course, we found out she was making up statistics to sell her course. Now I question anyone who claims they are an expert and cannot back it up with stats or even past businesses in the same category they are an expert in.

4. Not every project is meant for you, but it can show you what is possible. I have had many opportunities come into my inbox that have not come to fruition. It can be super discouraging, but I have learned that it is just an opportunity to show you what is possible. About 5 years ago, I was asked to write an article for Domino magazine. I wrote the article. They said they loved it. And I waited patiently for it to be published. After a month, I followed up to see when that article would be written and I was told they passed on it. The same thing happened, just a few days ago, with an opportunity to be on a national morning show that ended up not happening. But those opportunities have shown me what is possible for my career.

5. Don’t focus on what other people are doing, stay in your lane. This one is so easy to do when you are starting out. I had been doing my organizing business for a few years, when The Home Edit started their Instagram account. Immediately, I started comparing my business to theirs. They were traveling, so I thought I was supposed to travel. They were working with celebrity clients, so I thought I was supposed to do that as well. But I hate traveling and I don’t know any celebrity clients. I also didn’t want to work for free. Instead, I decided to stick to what I enjoyed. I put on my blinders and stayed in my lane. And I have been happy ever since!

What person wouldn’t want to work doing something they absolutely love. You are an incredible inspiration to a great many people. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

My movement would be to create calm in your home by clearing unnecessary clutter. I feel that when your home doesn’t feel like a junk drawer, you are able to relax. And when you can relax you can be more thoughtful, you are less stressed and have more patience. And I think everyone needs more patience in their lives. Now I didn’t say “organized” I said “clear unnecessary clutter” because I think people have a distorted view on organizing. It doesn’t have to be Pinterest-perfect, it just needs to work for you. If everything had a space to go in your home, then you should feel organized.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

My favorite quote “Organizing Is Like Yoga, It’s A Practice” -me

It is relevant to my life because everything is a practice. So, when I am creating content, helping families virtually organize or supporting online business owners, I know that what I am doing is a practice I need to do over and over to get better at my skills. It is something that everyone has to do every day. You aren’t going to organize one space once and be done. You have to do it over and over in order for it to become natural. This goes with everything in your life. You have to create a practice in order for it to become natural. I remind myself of this daily because as a business owner, I need to remember that not everything comes easy at first. I need to continue to practice to get better.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

There are a few! Obviously, Joanna Gaines. I would love to learn more about her business processes and how she balances being in the public eye along with setting boundaries. Martha Stewart is another person I admire based on how she created a brand for herself before it was even a thing. Nancy Carlson, the children’s author, has always been an inspiration to me as well. I have wanted to write a children’s book since I was in 4th grade and her books were stories I loved as a child. Same with Kate DiCamillo. When I was teaching, I would read her books and want to write like her. I loved the stories she told.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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In-depth Interviews with Authorities in Business, Pop Culture, Wellness, Social Impact, and Tech. We use interviews to draw out stories that are both empowering and actionable.

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Jason Hartman

Jason Hartman

Author | Speaker | Financial Guru | Podcast Rockstar

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