When Is It Time to Strike Out on Your Own? 8 Entrepreneurs Weigh In

Entrepreneurs are plentiful on the Internet, and many of them have successfully transitioned from “regular” 9-5 jobs to working for themselves.

I asked a group of these Internet entrepreneurs when they decided it was time to strike out on their own. Their answers varied, and they’re below, but one thing is perfectly clear:

only you know when it’s time to strike out on your own.

Nobody can tell you when you should leave your day job for the potential reward (and guaranteed risk) of self-employment.

But we can learn and be inspired by the stories below.

  • When is it Time to Strike Out on Your Own? 1 of 9
  • "I wanted to start a family and have a good quality of life." 2 of 9

    Merissa Alink from Little House Living says: "My husband and I were ready to start a family and I knew that I did not want to be a working outside of the home mom. But I also knew that I wanted to continue working to help provide for my family and I just happen to love to multitask. Now I feel so lucky to be able to do exactly what I wanted to always a mom, but still be a writer. I'm actually making more now than I could make by working part or full time in my local area."


    Image by Little House Living



  • "I had too much work." 3 of 9
    Jason and Jennifer

    Jennifer Bruce from New Season Design said, "For me, the time to quit the day job was when I starting having enough work available through our home-based business that I could no longer get it done if I kept the day job."


    Image by New Season Design

  • "I was making more money." 4 of 9

    Cat Alford of Budget Blonde said, " the "aha" moment was bringing in more money than the day job. That's when I knew it was "safe" to switch."


    Image by Budget Blonde

  • "I could reach more people." 5 of 9

    Jana Lynch of Bloggers Helping Bloggers told me her tipping point " was realizing I could help and reach more people--and potentially earn more money--running my own business than being chained to my government job."


    Image by Bloggers Helping Bloggers

  • "I was far happier." 6 of 9

    Jen Smialek of the Happy Homeowner noticed it was time to make the switch when "a good friend pointed out that I was far happier talking about my freelancing work than I ever was while talking about my work at the start-up I worked for at the time and asking me when I was going to strike out on my own for good. Bonus points was realizing I was making more money doing things I love!"


    Image by Happy Homeowner

  • "Giving up wasn’t an option." 7 of 9

    How did Carrie Smith of Careful Cents Freedom Course know it was time? "When I realized that giving up my "side hustle" so I could focus on my job wasn't an option. I loved my own work more than my day job -- and that was saying something!"

  • "When I felt the pain." 8 of 9

    Stephanie Halligan of the Empowered Dollar saw a quote by Sean Ogle that said, "When the pain of staying is worse than the pain of leaving, it's time to make a change." The quote spoke to her, and she struck out on her own.


    Image by Empowered Dollar


  • "I never considered a traditional 9-5." 9 of 9
    Samar pic

    Samar Owais never even went the traditional route. She says, "Last semester of college. I'd reviewed an event I'd gone to as a favor to a journalist friend who couldn't make it at the last moment. I wrote it, sent it in and forgot all about it...until I received a check a couple of weeks later. I hadn't even realized I'd be paid! And like any clueless 22-year-old, I jumped into freelancing feet first thinking I'd think about getting a full time job if I found the right opportunity. I never looked and instead focused on freelancing full time."


    Image by Samar Owais



Babble’s teamed up with espnW to share even more inspirational stories on unleashing your inner champion. Find them all here.

Article Posted 3 years Ago

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