Why Every Entrepreneur Needs to Join Challenges when Ditching the 9-5 Life

Why Every Entrepreneur Needs to Join Challenges when Ditching the 9-5 Life

Mar 16, 2022

Is it really necessary to add new challenges to your life? Yes.

Just being an entrepreneur may seem like a challenge. It’s clear to me having this blog.


Simply thinking about going from employee to entrepreneur may feel like a challenge. I get it.


Taking every step on the journey out of the 9-5 and into your next chapter brings a set of challenges. So why would I commit to a specific challenge that requires daily attention and time set aside on my calendar?


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use a calendar to plan a fresh start in your business

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There are 3 reasons I chose to do a 30-Day Challenge twice in 6 months.

Reason #1: I am naturally competitive with myself.

Reason # 2: Growing and learning is important.

Reason #3: Creating new connections.


No, this isn’t about networking per se. It’s actually about not having an office to go to. A breakroom to chat in. I’m guessing that any of you who have been part of a corporate team are familiar with “challenges” – we used to do them in every 9-5 job I had.


  • Weight loss/eat healthy
  • Make the most sales
  • Bring in the most clients


Challenges were something I promoted and ran many times in my gig overseeing a national staff training and leadership program. So why wouldn’t (and why shouldn’t) that be something I do in my entrepreneur life?


Without a given group of workmates to do a challenge with, connecting with people who share the same interests and needs as me is important.

sitting alone is not beneficial

Photo by YL Lai on Unsplash


What challenges did I do and why? Self-care and blogging because both are important for me.

The 30-Day Mental Health Cleanse

Funny story: I found that with my Free At 50 life… I’m already doing a bunch of these things. That said, being deliberate about them and learning some new ways to mentally cleanse made this challenge one I value highly.


In fact, I left it with being deliberate each day to do something from the cleanse list. It’s on my calendar to choose a cleanse activity. But it’s not hard because so many of them are part of my day-to-day.


Things I’ve been doing:

  • Exercise – for me this is innate to living in my new home, Colonial Williamsburg. Moving to Virginia from Michigan means a milder climate and easier for me (mentally and physically) to get outdoors. We walk around the historic area a ton. That said, I am not a ‘gym person’ so being outdoors is motivation for me!
  • Brain dumps – I was very aware of this concept but not doing it. At least not regularly. Now, after this challenge, I have it in my calendar once a month to make sure I do it but that said, it’s a formality. I find myself consciously feeling the need to brain dump and am doing it without being prompted.
  • Practicing gratitude – this really is a daily thing for me. I think it daily, it’s mentioned in discussions daily, and of course- I even bought a shirt with "Grateful" written on it so I’m reminded whenever I see it in the closet or throw it on! However, my updated version after the challenge: setting a timer and journaling things I’m grateful for.

Photo by Daphne


New actions I’m taking because of the challenge:

  • Doing something without guilt. By being intentional about it, a weight is lifted! This is vital for us entrepreneurs building a business and not yet “rolling” in income. Keeping the negative thoughts away and allowing needs over guilty feelings makes a difference.
  • Unplugging for a set amount of time. Sometimes it happens naturally but now it is a habit. I make certain to unplug, no peeking online for 1-3 hours daily. It keeps me present. Even if I’m alone; I read, cook, do something that doesn’t require thinking about the rest of the world, including my business. In fact, this makes me MORE productive and gives me clarity when I start to feel overwhelmed.
  • Deliberately avoiding complaining for a whole day. You’d be surprised at how difficult this honestly is and how much better you’ll feel only spewing out positivity for a full day.


My goal: build habits that keep me mentally ‘cleansed’ and enjoying every moment possible.


RELATED: The 30-Day Mental Cleanse Challenge by Ambitiously Alexa (click here to check it out)

preface with focus

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The 30-Day Branded Blog Challenge.

You might think I did this because I’m a blogger. Kind of.

What I have realized is that all entrepreneurs need a blog. Not necessarily on the level of this one which is the focus of my business, but as an enhancement to any business.


Having a blog section on your website or a separate blog linked to your business can give you credibility, help build a rapport with your clients, and share your unique perspective. It does this all while helping people- for free! Ultimately, they will value you and, potentially, work with or buy from you.


This challenge is like it sounds: 30 days, but self-paced.


Yes, you can do it self-paced but what makes it special for me:

  • It is for life. I will always have access to the ideas upon which I can create content, as well as information about marketing and promoting my blog.


  • It is a community. Remember how I said in the beginning, we’ve done challenges in the office over the years. But now we do not have our co-workers that we run into in the breakroom.


As entrepreneurs, having a community focused on the same goals we are focused on is motivating. Through Zoom calls and conversation threads, this challenge fills a noticeable void for me.


The challenge gives me a way to share valuable information with you in a relatable (and sometimes fun!) way. Giving writing a spin like “write a blog post as if you were giving a TedX talk” or “clear up misconceptions about your profession” is both inspiring and interesting! I have 30 days of prompts and creativeness to reference.


RELATED: Join the 30-Day Branded Blog Challenge here.

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Breaking it down: How do you find the right challenge?

Step 1: Determine what you’re looking to find.

  • What do you want to accomplish?
  • What do you want to change?
  • What do you want to learn?
  • What do you want to explore?


Answering any and all of the questions above give you a starting point.


Step 2: Get the challenge that’s right for you.

Google it. There is SO. Much. Out. There. But don’t just use Google, use Pinterest and even social platforms like Facebook to find a challenge to meet your goals.


Talk to people. Ask people who you know have similar interests and goals as you about any challenges they’ve come across. You can do this in real life but use your online network too!


Take advantage of opportunities. Both of the challenges I wrote about fell into my lap if I’m honest. I follow Alexa’s Facebook group and latched on to her 30-Day Mental Health Cleanse because she made it simple to implement and drew me in quickly with the daily content.


I did the Branded Blog Challenge, hosted by my new friend Marilen Crump after meeting her for coffee. We met after finding out in a Facebook group that we both lived in Virginia’s historic triangle. Small world, big internet, bigger benefits!

globe indicating how big and small the world actually is

Photo by Juliana Kozoski on Unsplash


Conclusion: joining a challenge is very important for anyone on the journey out of 9-5 life.

It doesn’t matter how you approach challenges.

You can start any time (not just January!). You may want to stagger challenges and do them throughout the year.


It honestly doesn’t matter which “30 days,” or 7 or 3 you choose, just do it! Of course, if a challenge starts on a specific date and you cannot participate for some reason at that point in time, you can always find out if it’s something you can do after the fact (will there be videos you can watch on replay for example?).


Doing a challenge when you are motivated to do it, when it fits into your life, your schedule and your goals is important. Don’t wait for the “new year” to get started.

take the time to do a challenge

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You can do one or do several.

Just don’t overwhelm yourself! Make sure what you commit to, you can participate in. For your own satisfaction and to stay motivated, it’s important to be clear about your commitment.


Whatever challenge you choose, it can lead to habits, a valuable part of entrepreneurship.


RELATED: Maggie Perotin’s Create ONE Good Habit for Good Challenge- we talk about habits and the challenge in this video. Watch, get motivated to create habits and take a challenge!


Share in the comments section any challenges you’ve taken, are taking, or are looking into! Join the Ditching the 9-5 Facebook group by clicking here and share with the community.

feedback is important

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