Failure on the Journey to Success (with Jaclyn DiGregorio): Episode 275

In this episode I’m talking to Jaclyn DiGregorio all about failing forward, and how big of a part failure is on the journey to success! Jaclyn DiGregorio is a life coach, motivational speaker and best-selling author. Jaclyn's passionate about helping people create lives they want to live.

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  • Jaclyn talks about how it’s okay to change your mind. Give yourself permission to try new things, and as you go through life, it’s okay to change what your dreams are. As she started working in the corporate world, getting her dream job, she still didn’t feel fulfilled. She knew if she worked for herself, she would feel that fulfillment.
  • Theres a lot of power in just STARTING. When Jaclyn first got started as an entrepreneur, she wrote down a bunch of ideas and set a deadline for her first launch of portion control plates. She spent $10k on creating a product, and it failed. After trying to launch an app that also failed, she almost started applying to corporate jobs. But her dad told her she’s not a quitter…. so she kept trying.
  • Ask yourself, “What’s working?” If you change your mindset from nothing’s working, to actually making a list of what is working, your mind will shift.
  • What does your dream life look like?
  • “Your success is inevitable as long as you don’t give up. The only failure is giving up.” You will find a way, you will MAKE a way, as long as you don’t give up.
  • Jaclyn says her biggest day-to-day struggle is mindset. She says that she is constantly pushing herself to grow. The reason this is so important to her is to:
    • 1. Set an example of what’s possible.
    • 2. To reach true fulfillment which in theory is our “full potential.”
  • Ways Jaclyn challenges her limiting beliefs:
    • She researches people who are doing things she doesn’t think are possible.
      • Ex. Limiting Belief: It’s not possible for a life coach/speaker to make $100,000 a month.
        • She finds people with businesses similar to hers that are successfully doing just that.
    • She looks for examples in her own life:
      • Ex: In order to be successful you have to work really hard.
        • This wasn’t working for her.
        • So she challenged this idea by asking herself what if she could work 40 hours or less and still have a successful business? She also asked herself this when she effortlessly attracted success and this helped her to see that this was possible.
  • “In life you get what you have the courage to ask for.” Such a powerful quote. You can have it all. Jaclyn says that you can only have the life you believe you can have. And you have to know you’re worth and your potential.
  • Jaclyn says that by opening your mind to what’s possible and then shift it to inevitability, this will change your life. These things will come to you once you realize it’s possible.
  • Courage = Belief > Fear
    • Fear doesn’t go away. Insecurities don’t go away. We’re all human and we all have fears. But Jaclyns advice is to raise the belief. Make that greater than the fear. Sometimes the next step is eating a healthy meal and getting 8 hours of sleep. Then maybe it’s doing all your laundry. Then the next step is to make a list of 3 ideas for your next business idea. The next step doesn’t have to be huge. It just has to be a step. Ask yourself: What might the next step be? (Hint: There’s no wrong step. The only wrong step is not starting).
  • Each step you take illuminates the next step. The lantern lights up the next 10 steps as you walk. Your steps come from your intuition. You can’t see the whole road ahead of you, but as you keep going, you’ll see the road to success little by little.
  • Your failures teach you what didn’t work. Keep going and this will build your self belief.
  • One person can impact millions. Never underestimate your impact.


  • (1:25) A little more about Jaclyn and how she got started.
  • (3:31) How Jaclyn switched up her career path from a corporate job to an entrepreneur.
  • (5:10) How Jaclyn overcame multiple failures at the start of her entrepreneurial journey.
  • (7:52) Ask yourself, “What’s working?”
  • (9:03) The power of following your own path.
  • (10:14) The “not so over night” success.
  • (11:38) Once Jaclyn “made it” what problems came up in her business?
  • (12:16) Life is 50/50.
  • (17:41) How Jaclyn challenges her limiting beliefs
  • (21:50) Ask yourself open ended questions and look for the answer in your life.
  • (23:44) Jaclyn’s advice to someone who just failed recently.
  • (26:30) Each step you take illuminates the next step.
  • (28:16) Some of Jaclyn’s favorite books.
  • (29:34) What does it mean to Jaclyn to make an impact?
  • (31:11) Where to connect with Jaclyn.


“You don’t know what you don’t know.”

“It’s okay to change your mind.”

“You are not a quitter.”

“Stop waiting to live the life that you really want.”

“I’m so grateful I kept going.”

“Your success is inevitable as long as you don’t give up. The only failure is giving up.”

“Life is 50/50.”

“My biggest fear is settling, so I’m never going to do that.”

“In life you get what you have the courage to ask for.”

“Our ego always wants to be right.”

“There’s nothing stopping you, other than you.”

“We don’t have to change the world, we can just change one person’s life and it does change the whole world.”


Connect with Jaclyn:

Podcast: Spark Your Light

Instagram: @jaclyndigregorio


Books mentioned in the episode:

Dollars Flow Easily to Me by Richard Dotts

The One Thing by Gary Keller

Watch Full Episode:

Failure on the Journey to Success (with Jaclyn DiGregorio): Episode 275

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Hey! I’m Rachel. I’m a former Big Ten volleyball player turned entrepreneur and professional cheese taster (kidding–but that would be a sweet job).

I’m a Pinterest strategist for female entrepreneurs who are sick of struggling on Facebook & Instagram and want to automate their traffic and get more leads on autopilot. I’ve used Pinterest to increase my blog traffic by 34,000/month…for free!

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