5 successful women give advice they wish they would have taken in their 20s

They may be at the top of their game now, but these accomplished executives wish they would have heeded this early career advice.

Our 20s are a time of tremendous career growth and learning. But this doesn’t come without some hurdles and hiccups, even if you ultimately end up as a successful professional or entrepreneur. We spoke to successful women about their own regrets in their 20s. Everything may happen for a reason, but if they could rewind time and change their approach, they could have fine-tuned their journey to the top. From taking advantage of having no strings attached and seeing the world to raising your hand and asking questions, here is the advice these women business owners wish they would have taken.


In her 20s, Amanda Bradford, founder and CEO of The League, was busy. By the time she reached 29 in 2014, she was building her now uber-successful dating app. To date, The League has a 1.5 million person waitlist across 60 cities domestically and internationally, and has grown 100% year-over-year since its launch. Now 34, Bradford is happy with the success she’s found and the connections she’s been able to foster, but she wishes she would have taken the advice of her former boss at Google who urged her to go see the world. “Anyone who takes that leap of faith and moves abroad to continue education or work rarely regrets it. For me, global work experience and travel are key contributors to business and personal fulfillment. I wish I had invested more in global exposure during my 20s,” she says.

Launching a company didn’t allow her the time or flexibility to pack a bag and go:

I wish I had traveled and forged my own global experience in my 20s because now it’s just too hard. I’m devoted to The League and its rapid growth. As the app expands into international cities–already in London and Paris–it would be helpful to have firsthand knowledge of each market and a network of people on the ground.


In a world that’s ripe with farm-to-table options, Suzanne Simon had a different idea: farm-to-taco. In 2013, she created Chaia Tacos in Washington, D.C., at the White House Farmer’s Market. At the time, First Lady Michelle Obama had launched the “Let’s Move” campaign, and it inspired Simon (and her business partner) to source local vegetables and develop seasonal recipes, honing in on sustainability and healthy eating. Though her 13-year-old daughter was skeptical of squash tacos, they’ve sold more than 1 million to date.

Growing her business, Simon wishes she wouldn’t have been afraid to ask questions. As the oldest child of two younger sisters in a divorced family, her mom worked long hours, leaving her siblings to care for themselves. When she reached adulthood and took her first gig at an environmental consulting firm in Washington, D.C., she felt like she still needed to have all the answers without posing any questions:

I remember worrying about a project, and my sister said, ‘You know, you don’t have to solve every problem and know everything.’ If I had taken her advice at the time, I think I would have been more focused on solutions and would have gone into making mistakes with more confidence. It has taken me many years to learn to let go, accept mistakes, and realize that I can’t control everything. Take advice—and outsource.

Much like not being able to ask questions, the best advice from Ali Grant, founder of Be Social PR, to twenty somethings is to, well, take advice. “I thought I could do it all and knew it all. Turns out, I didn’t. I made a lot of mistakes in leadership and large business decisions that ultimately caused a lot of unnecessary stress,” she continued. Even with early hurdles, now that she’s more than six years into business, her company has grown from barely hitting five figures to a multimillion-dollar business. And in the past year alone, she’s seen 51% growth.

It’s because she’s been able to listen to others’ wisdom and outsource areas she’s not an expert in that she has met and exceeded objectives. She didn’t listen right away, though, to people like her uncle, who encouraged her to hire a payroll company or hire a bookkeeper:

Hiring someone that specializes in bookkeeping is essential. Now, our accounting team is one of the most valuable parts of the business. You can’t know it all, especially at 24 years old. I wish I would have absorbed more advice from a strong mentor and other seasoned business leaders, so I could have avoided the mistakes I made. Change your attitude and you’ll change your income.

After high school, Ronda Jackson was working for a door-to-door sales company selling multipurpose cleaner. Every day, the “car handler,” as she called him, would repeat this mantra: “Change your attitude and you’ll change your income,” as they went from neighborhood to neighborhood. She wasn’t making sales–or having a good day–and didn’t listen. Now, as the founder and chief workplace stylist for Decor Interior Design, Inc., she wishes she would have listened:

I later learned that limiting beliefs inhibits your capacity, ambition, prosperity, relationships, health, quality of life, and ability to make a meaningful impact on the things you care about most. Looking back, it was a brief life lesson not about selling soap, but instead not letting your current circumstances get in the way of who you want to be.

Her outlook definitely changed for the positive, since what once started as a one-woman show has grown into a multimillion-dollar firm that is in the Inc. 5000.


When you’re such an overachiever that you decide to audition for American Gladiators on your wedding day, you know you’re the type of person who doesn’t slow down. After six weeks of filming, Ally Davidson became the Grand Champion but had to wait three months to spill the beans. She took that prize money and turned a lifelong dream into a reality, launching the first Camp Gladiator in Dallas. As the cofounder and co-CEO, Davidson’s brainchild is on track to exceed $60 million this year, and has an impressive 950 partner trainers that provide more than 4,000 locations across North Carolina, Louisiana, Tennessee, Texas, Colorado, and Florida. This equates to around 90,000 campers attending Camp Gladiator in any given month.

If it sounds like a fast-paced, bootstrapped business, that’s because it is. Now in her early 30s, Davidson wishes she would taken the advice of her business coach and given herself more of a break instead of pushing full throttle:

When you’re constantly going at 100 mph, you will make mistakes and lose focus along the way. Every year, your priorities will continue to shift, and all of a sudden you don’t have the same time, energy, or focus you once had. But that’s okay. You have to learn to let the little things go, pick a few things to really focus on, and always make sure you have good harmony in your life to give yourself the breaks you deserve.