Annika Caldwell and Skyler Johnson are aiming to make legal and financial matters a lot less intimidating, especially for young women and moms.

The women, who each have their own business, have teamed up to help other busy women, mothers or families navigate the worlds the law and finance to achieve their own hopes and dreams.

As entrepreneurs, Caldwell, 26, a financial coach, and Johnson, 35, an attorney, also want to serve as an example to encourage other women to explore collaboration as a means to accomplish their goals.

“One of my focuses this year is collaboration,” said Caldwell, who is certified as a financial coach by Ramsey Solutions.

She emphasizes the advantages of collaboration over competition.

WDAY logo
listen live
watch live

“In this day and age, it’s easy to compare ourselves,” Caldwell said.

Scrolling through Facebook and Instagram, women may feel intimidated by evidence of others’ success but, instead, they should see in such information the potential for collaboration, she said.

“I wanted to collaborate, and I wanted to collaborate with other moms,” she said. “I was looking for someone who could challenge me in my business and provide a perspective outside of my business.”

Johnson, whom she had met at church, came to mind because “legal and financial planning go hand-in-hand,” Caldwell said.

Though Johnson wasn’t well-acquainted with Caldwell -- and a little skeptical, “because lawyers don’t usually collaborate with non-lawyers,” she said -- she agreed to meet her for coffee at Starbucks, and the two hit it off.

“We had so many ideas,” Johnson said. “We just clicked.”

“I recognized working with Annika as an exciting opportunity,” she said.

And the women soon realized that the people they were trying to reach had a lot in common.

They stayed and talked at Starbucks until closing time, she said. And, along with a new friendship, a new partnership was formed.

“We both have a passion to educate others,” Caldwell said. “Often, people don’t know they need your services; they don’t know there’s a better or more secure option.

“Sometimes, you don’t know what you need until it’s too late.”

‘Helping everyday families’

Last fall, the two women hosted a webinar aimed at “helping everyday families in North Dakota and Minnesota that needed some help planning for their futures,” said Johnson, of the event that attracted 60 registrants. “We were really happy with that. For our first time out, it exceeded our expectations.

“We each have a unique area of expertise -- Annika is known as ‘the Budgeting Queen of the North,’ while I get overly excited about drafting trusts,” Johnson said. “We are eager to share our perspectives stemming from our own personal experiences in business. Simply put, collaboration births new ideas and possibilities.”

In the legal field, change comes slowly, she said, but younger lawyers are seeing opportunities to connect with clients in new ways.

“One of my focuses is getting out into the community, instead of waiting” for clients to find her, Johnson said.

This has prompted her and Caldwell to host “coffee and crafts” events, where moms can learn about legal and financial topics while their children are involved with a fun craft project, she said. “It’s like meeting at a playdate.”

Another such event is planned for March at the East Grand Forks public library, she said.

“Money and law are not exactly fun subjects,” Johnson said. “They’re subjects that people aren’t necessarily comfortable with.”

Lawyers can sometimes convey “an air of pretentiousness,” she said.

Johnson stresses the importance of “not talking down to” listeners, noting that “younger people really value relationship-building.”

Busy lifestyle

Each woman has a busy lifestyle in her role as entrepreneur, wife and mother; and each is raising three young children.

“It’s busy around here, to say the least,” said Johnson, who conducts a law practice called Sage Legal with her husband, also an attorney. She specializes in estate planning.

In Caldwell’s business, 23 and Debt Free, she helps guide clients, of all ages and backgrounds, through a process to accomplish their financial goals. The business name came about after she and her husband made the final payment on a $97,000 debt when she was 23.

“A financial coach will walk alongside you and look at your overall plan,” Caldwell said. “It’s a very big-picture role that we have, but there’s also a nitty gritty side to that.”

She helps clients analyze “the choices they are making every single day, and (if) those are having a positive or negative impact,” she said.

“Our main goal is to help people take control of their finances through budgeting, cutting costs and dumping debt, so they can cash flow their goals and dreams. And what that looks like for each client is very different, because every client has a different situation and every client has different goals.”

Collaboration as key to success

The two women view themselves as part of a larger trend in business.

“The truth is, female entrepreneurs are taking the economy by storm,” said Caldwell, adding that mid-level marketing companies are making impressive strides by their use of teams.

Based on data collected at the state level, “the growth, even from two years ago, that they were seeing in female-run business, is phenomenal. (Women) are changing the economy as we know it.”

Their roles as young, working moms are important factors in their ability to connect with others, Caldwell said.

“I think we reach a population that your standard bank or law firm can’t reach because we are moms,” she said.

And, working with Johnson, “I truly believe we are stronger together,” she said.

“She is able to reach people I’ve connected with, and I’ve been able to reach people she’s connected with,” Caldwell said. “We make each other better; we challenge each other and, honestly, she makes my business better, and I hope I do the same for her.

“We want to encourage women to do the same thing.”

Johnson holds the same point of view.

“We’d like to inspire other women to build connections and take a chance, because we are so much more powerful as a tribe than by ourselves,” she said. “We hope that other women would be motivated to see fellow females not as competitors, but as allies.

“We can walk through the doors of opportunity together … in our stilettos.”