How to quit the guilt and go after your dream business in 2020

“What is your business dream?” I asked her.

“I want to be a media mogul,” she answered quickly.

“What’s getting in the way?” I asked

“I don’t know,” she said, shaking her head.

It’s a conversation that probably seems too familiar to some of you, especially my fellow multi-passionate entrepreneurs. We have dreams but we don’t know how to turn them into real goals to accomplish, because something always seems to get in the way.

I’m here to tell you, that thing is Guilt.



Shoulda, coulda, woulda.

Whatever you want to call it, it’s getting in the way of you going after your dream.

Here’s how you know…

  • Your “to do” list never gets smaller, it only grows.
  • You feel exhausted at the end of the day, because you’ve been running around for everyone else.
  • Things you used to LOVE doing now stress you out and you don’t know why.

Sound familiar?

My first client had big dreams, but didn’t seem to have enough time in her day to go after them.

I made her do a “time diary” – where she wrote down everything she did – every day, every week, every month, every quarter, every year. She wrote down all the personal and business things – from writing articles to driving to her daughter’s school. I not only made her write all of the items down, but had her note how much time it took and how much money she made off of it.

When we met again, I wrote everything on a huge chalkboard wall and then made three columns.

At the top of one was a heart – these were for things she loved to do, no matter if she was paid for them or not.

At the top of the second column, a money sign – this was for things that made money or built her brand (which ultimately would make her money).

Then the third column was the “guilt/should” column. These were for things that she had been “guilted” into, “volun-told”, felt like she “should” do them. She didn’t like them anymore. She didn’t make money on them, and they certainly didn’t build her brand.

I had her put checkmarks in the appropriate columns next to each item (and some things had more than one checkmark.)

When we were done, 2/3 of the checkmarks were in the guilt column and she was crying.

I hugged her and told her this was the GREAT NEWS! Now we knew what was getting in the way of her living her best life, because every time she said “yes” to a guilt item, she said “no” to her dream.

We came up with a three-step plan to fix it – get all the guilt items off her list.

  1. We set a deadline – three months away. By that date, everything would be gone and we would celebrate!
  2. The things that she had guilted herself into – she just stopped doing. She was the only one who was watching, so that didn’t matter. (This step gives you the confidence that you CAN do it, and helps you with step three.)
  3. She went to all of these various committees and said: “Thank you for the opportunity to serve on [insert crap assignment here], but I’m resigning effective [deadline date]. Who should I turn the binder over to?”

You’ll notice: She didn’t ask for permission to leave, she told them when she was leaving and asked who should get the binder/training/etc.

“What if they don’t let me leave?” she asked.

“Then we’ll drive to the president’s house in the middle of the night, leave the binder on the front porch and run off like we stole something,” I said.

Thankfully, we didn’t have to do that, although I totally would have! Everyone accepted her “resignation”.

The results:

  • Within six months, she had written and published her first book and was out on the book tour. She had also started a local radio show.
  • Within a year, she was able to quit her day job. The radio station expanded her show.
  • Within two years she launched a statewide radio show that airs Monday through Friday in a highly-coveted time slot and she started working on her second book.

As you look to 2020 – a new year, a new decade – isn’t it time you got some of those guilt assignments off your to do list?

Once you do, I promise you – you’ll find it much easier to say “no” to putting that crap back on the list.

To help you get started, I created a Time Diary Worksheet for you to download free.

Dawn Dugle is the CEO of StorySelling Solutions. She helps multi-passionate entrepreneurs harness the power of their story and turn it into a powerful marketing message that can transform their businesses. See how we can help you.

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