23 Sep The Art of Making Grand Plans

by Kalika Yap

I spent this past Sunday at the Create & Cultivate Festival in Los Angeles, the world’s largest festival for women in business.

Thousands of founders, creators, and leaders, all in one place. I’m so happy I was able to be there. Thanks to my entrepreneur friend Amanda Ma for the tickets! : )

Emma Grede was one of the keynotes. She’s the co-founder of Good American, a founding partner of Skims, and the author of a new book, Start With Yourself: A New Vision for Work & Life.

Near the end of her talk, she told us a story. At 28 or 29, she was so upset that she hadn’t “made it” by 30 that she made a big grand plan.

She’s days away from turning 44 now. And here’s what she said:

“Still, at this point in my life, I’m making grand plans. I feel like there’s so much in front of me.”

Read that one more time. Slowly.

Still making grand plans.

Making the plan is the easy half. Most of us have a grand plan in a notebook somewhere. The art is in the second half. Fulfilling it.

And that’s what the rest of her talk was about.

Twenty Years Before Anyone Noticed

The first question Emma got was about her personal brand. I loved her answer.

She said she has never once thought about building one. For years she just did her work. She focused on what was in front of her, which was building the company and making money.

Then other people started writing her story for her. She told us about 80% of it was right, and 20% she didn’t recognize at all. So she decided to tell it herself.

When she arrived in America, people said she had popped up out of nowhere. She had been working for 20 years.

Here’s how she put it:

“I just think there’s an order of operations.”

And this:

“People are trying to tell a story before they’ve got anything to tell a story about.”

I wrote The Little Brand Book, so you know I love a brand. And I agree with every word. Your brand is the story of your work. The work comes first.

Her order goes like this. Get really, really good. Build your reputation. Learn the fundamentals of running a business. Then do what you want with it, and nobody can tell you that you can’t.

My Own Grand Plans

Emma said something about herself that made me smile:

“I did start before I was ready. I had no business coming to America to start a denim company.”

On paper, she said, plenty of people were better qualified.

I know that feeling. I started my career in broadcast journalism, at CNBC and Bloomberg. In 1999 I left to start Citrus Studios. On paper, a journalist had no business opening a digital agency.

Later I invented Luxe Link, a purse hook. Then I patented it. Then I had to defend that patent in court, more than once. Nothing on my resume said I was the person for any of that.

And in 2016 I said yes to hosting the EO Wonder Podcast for the Entrepreneurs’ Organization (EO). I’ve been behind that microphone ever since.

That podcast gave me the chance to sit down with Jaclyn Johnson, the founder of Create & Cultivate. I had the pleasure of interviewing her in October 2022. She started the company in 2012, built it without outside funding, and sold it in 2021.

Then, in December 2023, she and her business partner, Marina Middleton, bought it back.

This weekend I got to stand inside what she rebuilt. If you want to hear how she thinks, the full conversation is here:

Listen to my EO Wonder Podcast interview with Jaclyn Johnson

Jaclyn made a grand plan, fulfilled it, and then made another one.

The 120% Trap

Emma told us she’s surrounded by men. They’re the investors, the board members, and the senior managers in her companies. And she has watched how they move for years.

The men do things over and over that, on paper, they have no business doing.

And the women around her? In her words, they were “fully baking their ideas, getting to 120%,” and then saying they’d wait and maybe do it next year.

I see this with my coaching clients all the time. The plan is ready. The person is waiting for a feeling.

The waiting looks responsible. It looks like research, one more draft, one more quarter of saving.

Emma was asked about the uncomfortable conversations that business partners wait too long to have. She said she isn’t a waiter. And then she said my favorite line of the weekend:

“The water doesn’t get warmer because you wait to jump in.”

The pricing change. The hire. The talk with your partner. The launch. Whatever you’ve been standing at the edge of, the temperature is the same today as it will be next year.

She had a line about decisions too:

“If you’ve got nothing to lose on the other side of your decision, you didn’t make a decision. You just made a comfortable move.”

Her advice was to get comfortable having something to lose, because that’s when you have something big to gain.

Start With Yourself

That’s the title of Emma’s book, and it’s the idea I’d love you to remember this week.

The book is built around what she calls “Old Thoughts.” These are the outdated ideas about work, money, and ambition that we repeat to ourselves until they feel like rules. Her argument is that you can catch an old thought and replace it with a new one.

She ended her talk on exactly this. She asked every woman in the room to find the thought she has been telling herself over and over, and to swap it for something new. She promised it worked for her.

“None of us have a full understanding of what we are capable of.”

The whole room had just sung her happy birthday. And she reminded us that life is long, and that it never happens when we think it’s going to happen.

So make the grand plan. Make it again at 44. And then do the part most people skip.

When you catch yourself waiting this week, say it to yourself. Make the grand plan. Then get in the water.

Your Step-by-Step Guide: Fulfill Your Grand Plan This Week

Step 1. Catch the old thought

Write your grand plan at the top of a page, in one sentence. Under it, write down the sentence you’ve been telling yourself about why you can’t move yet. I’m not ready. I’m not a numbers person. It’s too late for me.

Then write the new sentence right under it. Make it one you can believe today.

You can’t replace a thought you haven’t written down.

Step 2. Look at your three numbers

Emma tracks about 15 data points. She said it all comes down to three questions. Are you growing? Are you growing profitably? Do you have the cash runway to meet your goals?

Her rule is that you never, ever outsource understanding your numbers. She said it doesn’t matter if you’re not good at math. When you bring in a finance person, you stay close to that person.

Answer all three questions this week, in writing, with real numbers.

Step 3. Pick three priorities and repeat them

Emma said her job as a leader is to be “really repetitive.” Everyone in the company, top to bottom, should know where the business is going and what has to happen in the next three months.

When everyone comes together around just three things, the business moves forward. When everyone works on their own list, it doesn’t.

If your team can’t name your three priorities, say them again.

Step 4. Have the conversation you’ve been avoiding

Emma learned this at 26 or 27, when she acquired her best friend’s agency and the two of them had to decide what would govern the partnership.

“The things that you are most scared of, the things that you’re avoiding, they’re the conversations that you need to have.”

Anything about money gets written down. Her question was simple: where is the piece of paper? And she said to have the conversation before you need to, while you still have room to negotiate.

Name the conversation. Put it on the calendar.

Step 5. Make one move before you feel ready, within 48 hours

Pick the smallest real step on the thing you’ve been circling. Send the proposal. Raise the price for the next new client. Book the meeting. Post the job.

It should have a little something to lose in it. That’s how you know it’s a decision.

Do it within 48 hours, before the feeling of being ready has a chance to talk you out of it.

Want Company for Your Grand Plan?

Most of my coaching clients already know what they need to do. What helps is having someone next to them while they do it.

If there’s a grand plan you’ve been circling, I’d love to hear about it.

Book a discovery call

No pitch. Just a real conversation about where you want to go.

You’re more ready than you think. You’re doing just great.