Anyone that has been in a position that requires managing others or running a business can tell you that if there's one thing that will never go away, it's challenges. They show up when you least expect them bringing uncertainty to your career, testing your abilities (and your patience), but more importantly challenges help you grow.
I personally used these difficult times to reflect and use the obstacle as motivation to accomplish things that seem impossible. That's just me, though. Today, I've highlighted seven incredibly talented ladies that overcame challenges during the early phases of their business. These ladybosses illustrated how hard work, passion, and determination go a long way in making your dreams come true.
So how do they do it? Keep reading as female leaders explain the challenges, and lessons learned along the way.
1. Avoid isolating yourself from others.
“Throughout my career, my biggest challenge has been learning to deal with criticism--especially negative Yelp and Amazon reviews. When someone posts a 1-star review about the restaurant (or one of my books).... ouch. Even if it doesn't happen very often, it still hurts!" —Alexandra Franzen, Author, Copywriter, Writing Coach/Consultant, and Co-owner of pop-up brunch restaurant HunnyMilk.
Alexandra overcame this challenge by avoiding isolating herself. “Sitting alone in my bedroom, sobbing into my laptop, obsessing over the words that someone has posted online... nope. That doesn't help. I need to reach out to my community--friends, clients, colleagues--for encouragement, humor, and a healthy sense of perspective," Alexandra shares.
Reaching out--not drawing inward--is what helps Alexandra to move forward. She discusses this a great deal in her new book, You're Going to Survive, which is about how to deal with stressful, discouraging experiences at work.
2. Set specific office hours
Even though you run a business to have a flexible schedule, and to have the freedom that an office job can't provide, that doesn't mean that setting office hours won't work for you.
Especially if you have other obligations, for example, if you are a caretaker, you have small children, or your business is a side hustle. Any of these are going to require just as most time and attention as your business does. You'll have to master time management to make it work.
A gal that knows about this is Ashley Mason, owner of Dash of Social a social media consultancy for ladypreneurs, since a few months before launching her business, Ashley's mom was diagnosed with glioblastoma, grade IV brain cancer.
“These past 20 months have been a rollercoaster, and her doctors did tell us in April that she has less than a year left to live. I'm her caretaker three days per week, which is difficult to juggle with client calls and client work," said Ashley.
Ashley overcame this challenge in her business by having custom office hours to accommodate both her mom's schedule and her clients. Also, Ashley's clients are aware of her situation and support her 100 percent.
3. Trust yourself and your instincts
“One of the biggest lessons I've learned as an entrepreneur is to stop second guessing myself. My co-founder Christine and I never encountered any sexism while growing our business, and anytime us being women comes up it is always between us personally." —Helen Lee, Co-founder & COO, JOANY
Helen points out that sometimes we second guess ourselves and then look at our male counterparts who just say “yeah, let's do it" and they don't have that tendency to second guess. “In that way, it almost feels like sometimes we put the females stigma on ourselves. When that happens, we just need to look at each other and say “we've got this, we did our homework, and we know what we're doing."
“It's all about getting out of our own heads and trusting our instincts," Helen suggests.
4. Hire the right people
Paige Arnof Fenn.
When the time comes to expand your business take this new step slowly. “I started a global branding and marketing firm 16 years ago, and I learned that the people you start with are not always the ones who grow with you." —Paige Arnof-Fenn, Founder of Mavens & Moguls.
She wished she would have fire people that were not a good fit for her business a lot sooner. “I spent more time managing my employees than finding new customers. I knew in my gut they were not up to snuff, but out of loyalty to them I let them hang around much longer than they should have," says Paige.
If you hire employees or freelancers to help you and you feel that's not working out, then let them go. Write down your own job description of your ideal (not perfect) employee that includes qualifications, the day-to-day tasks she will perform and the must-have skills to be successful.
Paige shares, “it is true that you should hire slowly and fire quickly. I did not make that mistake again later on so I learned it well the first time. I wish I had known it even earlier though but lesson learned for sure!"
5. Not everyone is going to like you (and that's ok!)
“I have worked really hard to be comfortable with the idea that not everyone is going to like me. As women, we are taught that we need everyone to like us and that we need to be pleasing to others." —Katie Willcox, CEO of Natural Model Management
Katie feels that model doesn't work for business. “It takes time to be ok with the fact that there will be plenty of people who dislike you and even want to see you fail. The challenge is to not give those individuals power by wasting your time worrying about what they think," shares Katie.
Katie's takeaway: “I have learned that when you are dealing with other people, every person has a reality that is very different from your own. We all see things from our view, and we tend to believe that view is the correct view. I have learned as the boss, understanding where others are coming from is important, but at the same time you have to do what is best for your business."
She has the following advice for other fempreneurs, “have the uncomfortable conversations, hold others accountable, and you always have to keep evolving and growing as a business, regardless of what people say or think about you."
6. Work-life balance, the struggle is real
Many women struggle with the concept of work-life balance and know that cracking the code on finding work-life balance while running a business is difficult, but even more so when you also have to take care of children.
“Explaining to my seven-year-old why I can't be there for every school event, volunteer activity and birthday party can be a challenge. I find myself torn between doing my best for the company, my team, and my customers versus the best for my family. While this family/job dynamic affects both genders, it hits females (especially females in positions of power) especially hard." —Dasha Moore, Owner and Chief Operating Officer of Solodev.
Dasha thinks that if anyone can do it, it's us, ladies. “I use the elements traditionally relegated to my gender to help me balance the unceasing hurdles of the work-life balance. Women are notoriously trustworthy planners, organizers, multitaskers, and negotiators – more so than our male counterparts," Dasha shares.
“Every morning I rise to the challenges of both womentrepreneurship and motherhood, wearing both hats with pride and embracing the challenges thrown my way as gifts rather than burdens," says Dasha.
Merin Guthrie. Photo Courtesy of Akil Bennett
7. Keep a positive attitude
“I think the biggest challenge is staying positive in the face of the everyday grind." —Merin Guthrie, CEO of Kit.
Merin points out that as an entrepreneur, you're always facing steep odds and you spend a lot of your time problem-solving. “At first, every little challenge seems like a major failure. You develop a thicker skin as you go along, but the real way you overcome that feeling of being slightly overwhelmed at all times is by developing a relentlessly positive attitude and always looking for ways to fix issues efficiently and then keep moving forward," says Merin.
When you're feeling overwhelmed, go for a walk. Something as simple as that can help you see things more clearly. Another option is to jot down everything that's overwhelming you.
“It took me a while to figure out what issues were major issues and not get bogged down by the little things," shares Merin.
"Sh*t!" my daughter exclaimed as she dropped her iPad to the floor. A little bit of context; my daughter Victoria absolutely loves her iPad. And as I watched her bemoan the possible destruction of her favorite device, I thought to myself, "If I were in her position, I'd probably say the exact same thing."
In the Rastegar family, a word is only a bad word if used improperly. This is a concept that has almost become a family motto. Because in our household, we do things a little differently. To put it frankly, our practices are a little unconventional. Completely safe, one hundred percent responsible- but sure, a little unconventional.
And that's because my husband Ari and I have always felt akin in one major life philosophy; we want to live our lives our way. We have dedicated ourselves to a lifetime of questioning the world around us. And it's that philosophy that has led us to some unbelievable discoveries, especially when it comes to parenting.
Ari was an English major. And if there's one thing that can be said about English majors, it's that they can be big-time sticklers for the rules. But Ari also thinks outside of the box. And here's where these two characteristics meet. Ari was always allowed to curse as a child, but only if the word fit an appropriate and relevant context. This idea came from Ari's father (his mother would have never taken to this concept), and I think this strange practice really molded him into the person he is today.
But it wasn't long after we met that I discovered this fun piece of Ari Rastegar history, and I got to drop a pretty awesome truth bomb on Ari. My parents let me do the same exact thing…
Not only was I allowed to curse as a child, but I was also given a fair amount of freedom to do as I wanted. And the results of this may surprise you. You see, despite the lack of heavy regulating and disciplining from my parents, I was the model child. Straight A's, always came home for curfew, really never got into any significant trouble- that was me. Not trying to toot my own horn here, but it's important for the argument. And don't get the wrong impression, it's not like I walked around cursing like a sailor.
Perhaps I was allowed to curse whenever I wanted, but that didn't mean I did.
And this is where we get to the amazing power of this parenting philosophy. In my experience, by allowing my own children to curse, I have found that their ability to self-regulate has developed in an outstanding fashion. Over the past few years, Victoria and Kingston have built an unbelievable amount of discipline. And that's because our decision to allow them to curse does not come without significant ground rules. Cursing must occur under a precise and suitable context, it must be done around appropriate company, and the privilege cannot be overused. By following these guidelines, Victoria and Kingston are cultivating an understanding of moderation, and at a very early age are building a social awareness about when and where certain types of language are appropriate. And ultimately, Victoria and Kingston are displaying the same phenomenon present during my childhood. Their actual instances of cursing are extremely low.
And beneath this parenting strategy is a deeper philosophy. Ari and I first and foremost look at parenting as educators. It is not our job to dictate who our children will be, how they shall behave, and what their future should look like.
We are not dictators; we are not imposing our will on them. They are autonomous beings. Their future is in their hands, and theirs alone.
Rather, we view it as our mission to show our children what the many possibilities of the world are and prepare them for the litany of experiences and challenges they will face as they develop into adulthood. Now, when Victoria and Kingston come across any roadblocks, they have not only the tools but the confidence to handle these tensions with pride, independence, and knowledge.
And we have found that cursing is an amazing place to begin this relationship as educators. By allowing our children to curse, and gently guiding them towards the appropriate use of this privilege, we are setting a groundwork of communication that will eventually pay dividends as our children grow curious of less benign temptations; sex, drugs, alcohol. There is no fear, no need to slink behind our backs, but rather an open door where any and all communication is rewarded with gentle attention and helpful wisdom.
The home is a sacred place, and honesty and communication must be its foundation. Children often lack an ability to communicate their exact feelings. Whether out of discomfort, fear, or the emotional messiness of adolescence, children can often be less than transparent. Building a place of refuge where our children feel safe enough to disclose their innermost feelings and troubles is, therefore, an utmost priority in shepherding their future. Ari and I have come across instances where our children may have been less than truthful with a teacher, or authority figure simply because they did not feel comfortable disclosing what was really going on. But with us, they know that honesty is not only appreciated but rewarded and incentivized. This allows us to protect them at every turn, guard them against destructive situations, and help guide and problem solve, fully equipped with the facts of their situation.
And as crazy as it all sounds- I really believe in my heart that the catalogue of positive outcomes described above truly does stem from our decision to allow Victoria and Kingston to curse freely.
I know this won't sit well with every parent out there. And like so many things in life, I don't advocate this approach for all situations. In our context, this decision has more than paid itself off. In another, it may exacerbate pre-existing challenges and prove to be only a detriment to your own family's goals.
As the leader of your household, this is something that you and you alone must decide upon with intentionality and wisdom.
Ultimately, Ari and I want to be the kind of people our children genuinely want to be around. Were we not their parents, I would hope that Victoria and Kingston would organically find us interesting, warm, kind, funny, all the things we aspire to be for them each and every day.
We've let our children fly free, and fly they have. They are amazing people. One day, when they leave the confines of our home, they will become amazing adults. And hopefully, some of the little life lessons and eccentric parenting practices we imparted upon them will serve as a support for their future happiness and success.