Raise your hand if you ever overcomplicate things. You have the goal in your head & you’re ready to work, but you get overwhelmed at the thought of where to start. Working towards your dream won’t be easy. But the process should be simple. Enter the art of making a list. Where are my list-lovers?

There aren’t many things that don’t require a list for me. Even navigating through a Tuesday at home with my three kids requires a list, or else everything feels heavy & tangled in my head. When I don’t make a list, I will inevitably go to bed that night forgetting to pay for the kids’ school & text our babysitter to see if she’s free Friday night, and I’ll add in unnecessary items like ordering refrigerator magnets of my kids’ faces off of Mpix. Lists simplify. When we let lists run our lives & allow them to tell us we’re failures if we don’t cross everything off of them, they start to be a problem. But lists help us allocate our time & energy, & lists help us take a whole picture situation, like a Tuesday or a specific goal, & break it down into individual, achievable steps.

What’s your dream? Is it to run a half marathon? Or maybe it’s to be able to stay on the treadmill for longer than eight minutes? Is it to feel more confident at making dinner for your family? Is it to start an entrepreneur business or to work your way up in a company? Is it to be healthy? There are no limits to a dream, & no dream is too big or too small or too boring. Any area where you want to grow is a dream. Break that dream into achievable steps, & your dream just became a goal. Way to go, you.

10 Steps to being a boss with a dream just for herself

  1. Voice Dream Aloud (first to self—then to someone you trust)
  2. Picture yourself five years from now doing your dream. Be as detailed as possible.
  3. Believe you can get there. This is not hypothetical.
  4. Get your husband/person on the same page (If you’re going to be a team when it comes to parenting/life, communication is everything.)
  5. Ask for help (aka serve yourself some humble pie & recognize you cannot do this whole thing by yourself.) *This will possibly be the hardest step. And by possibly, I mean definitely.
  6. Make a schedule & treat your plan like a job. This isn’t dramatic play.
  7. Don’t put too much pressure on yourself. Your first day will not solve a major world problem. Unless you’re a unicorn.
  8. Remove distractions. If being home will leave you staring at that load of laundry or full dishwasher, go somewhere. If you are spending more time on Instagram than working, get rid of it.
  9. Recognize that you have set up trustworthy childcare and worrying about how your kids are doing while you’re away will not serve them or your work.
  10. Work! Write! Research! Outline! Dream! Breathe! Connect! Do all the things! And then go home refreshed and love your babies! WIN!

**Bonus Step (and possibly the most important. And by possibly, I mean definitely):

Don’t compare your steps or starting place or workspace or success with anyone. This whole dream you’re working on? It’s supposed to be life-giving. Every second you spend your time comparing is a second not investing in your dream, & it certainly doesn’t fuel your life. Don’t give in to the temptation. The moment creativity becomes a race or competition, it isn’t creativity anymore. It’s like loving with an agenda. That’s not actually love. And comparing isn’t actually part of your work. So don’t give it your time.


  1. Ginni on August 28, 2018 at 1:12 am

    Love this Jenna!! Your writing is wonderful and so inspiring! Thank you for sharing! Can’t wait to read more! And I am working on goals this week! 🙌🏼

  2. Court on August 28, 2018 at 2:34 am

    Loved this so much!!!!
    Love hearing your voice so clearly and love watching you thrive in your passion/calling!!
    And LOVED the intro line about how you want your girls to watch you achieve your goals!!’
    All so awesome!!!

  3. Kathy King on August 29, 2018 at 9:08 pm

    Love, love it❤️

    • Jenna Winegeart on September 2, 2018 at 12:52 am

      thank you for reading!

  4. Amiee on September 1, 2018 at 10:46 pm

    Yesssss! I needed to read this!!

    • Jenna Winegeart on September 2, 2018 at 12:51 am

      so glad you did!

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