I've been my own boss for 7 years. Here are 5 things I do every month to stay organized.

I've been my own boss for 7 years. Here are 5 things I do every month to stay organized.
Gaby Deimeke
  • Jen Glantz is an entrepreneur and the founder of Bridesmaid for Hire.
  • As a solo business owner, she has several habits to stay organized and make new connections.
  • Glantz takes a different skills workshop every month and meets regularly with two mentors.

I've been an entrepreneur for over seven years and while being your own boss comes with perks, it also has its downsides. I'm the only one responsible for generating income, figuring out how to innovate and when to pivot, and making big financial decisions.

When I worked full-time at a startup, the company encouraged our career development by offering workshops, hosting networking events, and encouraging time off to go to conferences. I enjoyed this networking, so when I left to go out on my own, I decided to be strategic about spending time bettering my skill set and my connections.

Now, I set aside time each month to do five things to ensure I'm growing, learning, and staying sharp as the sole employee of my business.

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1. Take a course or workshop

I'm self-taught in many of the key skills I use daily for my business, from SEO to video editing, so there's always room for improvement.

Every quarter, I map out four topics I want to learn more about and then sign up for one workshop per month. I search for free workshops on Skillshare and General Assembly, and if I need a more advanced workshop, I'll browse Coursera for classes that span several weeks or months.


2. Meet with mentors

Having mentors has been a great way to learn and receive feedback from people I respect and admire. I have two mentors who I speak to once a month to share what I'm working on and hear their suggestions and guidance on next steps to take. These are people I met at conferences, years ago, who were already successful in the industry.

I also have two unofficial mentors who I don't know personally but consume their content on a weekly basis by listening to their podcasts, reading their book, or watching their YouTube videos. I take away tips to help me stay focused and be more productive.

3. Do a professional audit

When you're running your own business, it can feel like your to-do list is always getting longer. To make sure I'm not overlooking something big, I do an audit of my business once a month.

I start by examining the website for bugs or broken links. Then I review my finances and credit card statement, and rescan my inbox to make sure I didn't miss any important emails. Doing this audit lets me catch mistakes before they become bigger issues.

4. Connect with other professionals

Being a solo-entrepreneur can be lonely. I make it a habit to schedule a virtual catch-up with a friend, former coworker, or Linkedin connection at least once a week.


I also use websites like Eventbrite and Meetup.com to find local networking or meetup a month events to meet other professionals in my area.

5. Take a break

One of the biggest things I've struggled with over the years is finding any kind of work-life balance. Now, I block off one day each month as a personal break. My rule is to spend the day offline and it helps me reset.

As a solo-entrepreneur, it's crucial to have regular practices in place that help you stay on top of your game. Whether monthly or weekly, these habits will pay off in the long run.

This article originally published September 3, 2021.