The Biggest Mistakes Women Entrepreneurs Make

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My travel blog has been my sole job for more than eight years. This was never my intention when I started, and when I walked out of my office on September 14, 2010, I assumed I’d be walking back into another within a year.

At the beginning, I didn’t even plan to make money. How did people even make money with travel blogs back then, anyway? All I wanted was to have one of the biggest travel blogs in the world.

But soon I started making money — $50 here, $100 there. A few months later, while sipping a coconut in Krabi, Thailand, I decided that I would try to earn $1000 per month — enough to live comfortably in Southeast Asia.

I hit that goal, and soon surpassed it. I tried new things, the money increased, and now I live in my own apartment in Manhattan while still managing to travel quite a bit. I get to work with partners who bring me to remote, otherworldly places like Antarctica and Western Australia, while still having time and money to pursue my own travel goals, like visiting every country in Europe.

That’s not all, though. I remember crying through a sweltering train ride in Bulgaria as I panicked over being down to $200 in my checking account and being owed more than $9,000 from various partners who weren’t paying on time. The trips I invested in, only to have partners cancel on me at the last minute. And the time I was gaslit by a group of male travel bloggers who insisted I was lying about never having been to The Gambia.

Not a lot of women in my position have survived for this long. We’re the exceptions in our transient industry.

I’m ready to share what I’ve learned. Here is the first in a series of posts highlighting digital entrepreneurship for women today.

Starting with the biggest mistakes that female entrepreneurs make.

Underestimating the Extent of Gender Inequality

We were raised being told that we could do anything just as good as boys could. This is especially true for those of us who were raised by second-wave feminists who came of age in the sixties and seventies. 

But the truth is that even today, women face constant obstacles in the workplace. Here’s just a taste:

  • 42% of women have faced gender discrimination on the job.*
  • American women make 80 cents for every dollar a man makes — but black women make 63 cents on the dollar, while Latina women make 54 cents on the dollar. Some studies measure it as far less.*
  • Men are four times likely to ask for a raise than women, and when women ask, they tend to ask for 30% less.*
  • Women CEOs only comprise 24 of the Fortune 500 companies, or less than 5%.*
  • Historically female-dominated industries tend to pay less than male-dominated industries.*

And this doesn’t end with entrepreneurship. Simply giving up an office and a boss doesn’t make you immune to the struggles. You still have to negotiate deals with partners. You still have to sell yourself to clients. And when you’re the face of your business, likability becomes a huge factor.

Success and likability are negatively correlated for women, which is the opposite of men. This has been shown in study after study.*** The attributes that help men become successful are interpreted differently for women. An aggressive male executive is labeled a go-getter; an aggressive female executive is bossy. A highly intelligent male coworker is brilliant; a highly intelligent female worker is full of herself. A father who puts in long work hours is providing for his family; a mother who puts in long work hours is neglecting her family.

Are these barriers insurmountable? No. But you have to acknowledge them if you’re going to fight through them.

What to do instead: Acknowledge that these differences exist and you’ll have to work much harder than a man in your position would. Spend extra time making sure your arguments are iron-clad to make them more persuasive. Reserve extra time and energy for your passion projects because you will likely need it.

Trying to Please Everyone

Women are raised to put others’ needs above our own, and we often interpret that as needing to please everyone. During our whole lives we’ve been told, consciously and unconsciously, that our role is to nurture, care, and support. Think of the jobs that are stereotypically assigned to women: nurses, teachers, secretaries. Each role is to be a caretaker, putting someone else’s needs ahead of their own.

Even if you become phenomenally successful in your business, you’re never going to be able to please everyone. And you’re not going to please your particular customers all the time.

And don’t I know it. If I cover Antarctica, someone complains it’s too expensive; if I cover Long Island, someone complains it’s too boring; if I cover Southeast Asia, someone complains it’s too far; if I cover Europe, someone complains it’s too cliché. Not to mention my favorite recurring comment, “You say you write for women but technically a lot of stuff in this post applies to men too!”

But you know what? If you’re good at your work, the majority of your customers will stick with you. Don’t beat yourself up over the fair-weather fans.

What to do instead: Accept early on that not everybody is going to be a fan. When criticism comes, it’s okay to be hurt — but let it go. It will become easier in time. If you hone your key product well, your core customers will stick with you.

Waiting for Perfection

From a young age, women are groomed to be perfect. This energy is often channeled in a positive way — women now outnumber men at universities in the United States — but more often it’s channelled in unhealthy ways.

How often have you stalled because you couldn’t get your product, or project, or even blog post to fulfill your high standards? As a result, many content creators often languish for weeks or months with no new content because they can’t live up to their own impossible standards. The vast majority of regular people wouldn’t even notice those imperfections.

One of the biggest problems, and one that I’ve often struggled with myself, is that women often won’t get their biggest projects off the ground because they can’t get it perfect before they launch. And instead of a product that does well, they end up creating no product at all, losing time and money on what they created, and remain at square one once again.

Perfect is the enemy of good. Remember that.

What to do instead: As far as your final products go, remind yourself that perfect is an impossible deal, and make peace with delivering a 98/100 if it saves your sanity.

Not Knowing How to Negotiate

One of the starkest differences between men and women in business is how they negotiate. According to negotiation expert Linda Babcock, most women don’t negotiate in the first place, and those who do tend to receive 7.6% less than men in the same position.*

In a traditional job, this could cost you thousands of dollars and years of your life. As an entrepreneur, this could be the difference between negotiating enough money to bring your business to the next level or having to close down within a year.

It could make the difference in working for yourself forever and having to go work for someone else again.

Want to learn more? Get my free guide on how to negotiate better as a woman.


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Focusing on the Wrong Areas to Improve

“Everything will be better if I learn how to pin the right way,” women entrepreneurs tell themselves, and they sign up for a $700 course on mastering Pinterest. “If I get more Pinterest traffic, things will finally start working for me.” Or maybe it’s a course on Instagram, or graphic design, video production, or branding. 

Of course you’re going to improve your skills if you actively work to improve them. But are you choosing the right areas on which to concentrate?

So many women focus on the wrong areas to improve. They lean into specifics when they should be focusing on generalities. It’s the equivalent of spending all your time and money learning how to do 10 different smoky eye looks while still washing your face with Liquid Dial. It’s like booking a trip to climb Kilimanjaro when you don’t even exercise in the first place.

It doesn’t address the root causes of your problems; instead, it simply paints a shiny veneer on a crumbling facade.

What to do instead: Invest in products that fix you from the core. Learn to fix what’s wrong before focusing on the bells and whistles. See the forest for the trees, not the teeny tiny pinecones that fall off the branches in May.

Bringing Their Romantic Partner Into the Business

I can’t tell you how many times I’ve seen this end badly. A woman builds a YouTube channel on her own, she grows her business steadily, she gets into a new relationship, and within a few months, “Ashley’s Vegan Kitchen” has become “Vegetarian Eats with Ashley and Blake.” 

Who the fuck is Blake?! Some guy who can’t give up cheese, apparently. 

Very often, women bring their partners into their business to share the benefits — time freedom, not having to work a traditional job anymore, location independence and the ability to travel the world. And often they do it to fix resentment issues in their relationship, where the woman has the “cool job” and her partner feels like he’s not providing adequately.

But their partners are often starting with a limited skillset and thus find themselves enjoying the benefits without performing equal work.

And very often, the relationship ends in a breakup. And the woman entrepreneur who painstakingly built up her business from scratch now needs to divide it up with someone whom she taught everything.

I get that you love your partner. I get that you think he or she has skills. But do not give away the keys to the castle.  

What to do instead: Don’t consider involving your partner until you’re married or at the equivalent level of financially-merged-forever-relationship. Even then, be cautious. If your partner has skills for which you were going to hire someone anyway — photography skills, programming skills, accounting skills — consider hiring him and treating him like a regular employee. Pay him a fair market rate, give him deadlines, treat him like you would any other vendor. 

Copying Every Other Woman in the Field

One of the reasons why I’m still a successful travel blogger nine years later when so many of the originals have given up is because I’ve always focused on originality. These days, a version of almost every generic travel post I write ends up on a variety of other travel blogs, often down to the same headings. That pushes me to write offbeat, different, and personality-filled posts that would be much harder for someone to blatantly copy.

Think of the famous “Follow Me To” Instagram account where the woman led her partner around the world, dragging him by the hand. Thousands of Instagrammers copied that account again and again. Did anyone else get famous doing that? No. It was too obvious that they were copying the people who perfected the theme and made it famous.

It’s easy to think that just because a certain woman was successful with her business, that things will play out for you the same way. They likely won’t. Some people are more successful because they started at a different time, because they have different connections, or because they have access to other resources. Most of what happens in a business takes place behind the scenes and a bystander wouldn’t be able to observe it.

And the worst part? If your industry is closely watched, it will be obvious to people that you’re copying someone else.

What to do instead: Sketch out a business based on who you are and what your strengths are. Constantly question whether you’re imitating something you’ve seen someone else do. Try to create something that nobody else has done yet, and push it hard.

Working Harder, Not Smarter 

Perfectionism often rears its head in strange ways. And it’s something that women do all the time, even when we don’t think we’re doing so. Toiling away at details that no other human would have noticed, only to realize you’ve spent several hours working on something that didn’t need fixing.

“But shouldn’t my work be perfect?”

You’ve been hired as a professional; you should be delivering quality work. But too often women waste time on things that don’t actually bring in money — agonizing over website plugins, newsletter sequences, the aesthetics of their Pinterest boards, and Google Bloody Plus when they could be equally successful with a pared down website. Too often women get bogged down in the details of things that don’t actually make a significant difference in your income, and as a result they don’t prioritize the work that pays.

What to do instead: Audit the work you’re doing and the income you’re bringing in. See what brings in money and what doesn’t. See how your time is best spent and what areas of your business you should be focusing on expanding. See what you can outsource and what you should handle personally.

What is the biggest lesson you learned from running your business?

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16 thoughts on “The Biggest Mistakes Women Entrepreneurs Make”

  1. Kate,

    Your content and unique is what has kept me and many others coming back over the years. I always look forward to your new posts and especially your year round ups of best and worst. Your content never reminds me of anyone else and I love that you are pushing yourself in terms of content. No other female travel bloggers I travel have been to Antarctica. While its not somewhere I would visit (I hate snow and cold haha), I absolutely adored your content and gorgeous photos.
    I cant imagine a travel blogging world without you at the forefront. I admire how your content has evolved with you having your base in New York. 🙂

  2. I absolutely love this, Kate!

    Something I personally struggle with a lot as a female entrepreneur is projecting my own emotions and insecurities into a situation that should be strictly business (i.e. “am I going to offend or upset someone by standing my ground?”).

    I work with a lot of men, and most of them don’t seem to have nearly as many qualms as I do when it comes to things like defending their service pricing, saying “no” to unreasonable requests, or asking other people to follow up on their end of the deal.

    I guess it’s because women are taught to prioritize being pleasing and polite, but I find that I’m way too quick to take the blame for mistakes that weren’t my fault, to say “yes” when I should probably say “no,” and to accept less money than my services are worth.

    Something my dad has told me again and again when I ask for his guidance is “it’s just business.” This has become my mantra, and has really helped me remove my own emotions from these business situations.

  3. I know another thing I’ve struggled with is mild imposter syndrome, which I know stems a lot from doing something (i.e. starting a business, being my own boss) that women aren’t traditionally “supposed” to do.

    I struggled for a long time with believing that I *deserved* to make good money doing what I was doing. Monetizing a website isn’t easy, but it’s doubly hard when you feel like you need to apologize for it. Once I got past that mental block, my business really started growing by leaps and bounds.

  4. Brilliant post, Kate! I so relate to it. Super helpful for new female bloggers like me. I’m sure this post and your guide to negotiation skills will help many of us to set and prioritize blogging business goals.

  5. I’m always so grateful to hear or read advice from women entrepreneurs for (aspiring) women entrepreneurs– and grateful to live in a time when those voices are easy to seek out. A lot of this hit home with me, particularly your points about focusing on improving in the wrong areas and needing to audit your time. Thank you for sharing! I’m walking away with a mini-checklist of ways to reevaluate where I focus my time and energy. Cheers!

  6. This is a FANTASTIC post. Thank you, thank you, thank YOU.

    I love reading your travel posts but I also love seeing other topics through your eyes since you have so much success and experience under your belt. As someone who has finally found a niche and is trying to launch a business that will allow me to full-time travel this post is exactly what I need to read right now.

  7. LOVE! I’ve been following your blog since 2011 and it’s been so awesome to watch you come this far. I am very excited for this new ‘series’ on digital entrepreneurship, and I hope it’s a success for you!

  8. Freaking awesome post, yet again, Kate. Even though I am a guy, I still related to a lot of the things in there, and it also brings up things I can do to break down gender walls and reduce my own subconscious stereotyping. Thanks for the great post!

  9. Kate,

    This was a meaningful and super impactful post! I’m a blogger that writes about feminism and is constantly trying to encourage women to say fuck it to perfection. You worded this so eloquently. It was very inspirational. Also, I couldn’t laugh aloud about “Who the fuck is Blake?” Super clever, but also super relevant. Thank you for inspiring a community of women and continuing to give all of us entrepreneurs hope in the new year and for many years to come.

    Much love and admiration,
    Martha

  10. Great article! Thanks for sharing. In my case definetely the “waiting for perfection” has been (and still is) a struggle. The biggest lesson I’ve learnt as an enterpreneur is to choose the right collaborators and only then be able to delegate, keeping in mind though that nobody will ever carry out a task exactly as you would, but that’s part of the deal.

  11. I could not agree more with all of this! I started my business a year ago, and so many of these topics resonate with me – I especially agree with be who you are and don’t try to copy other people, and also along the lines of knowing how to negotiate. A big thing I’ve experienced first hand and seen from other female business owners is never charging enough because we don’t want to seem too demanding or greedy. But we need to know our worth and know we ARE worth that amount!

  12. There’s some good advice here but some of it left me scratching my head. Just because YOU started blogging in 2010 and did things a certain way doesn’t mean that new bloggers starting out today can follow the same path and find success. I spend plenty of time “agonizing over Pinterest boards and newsletter sequences” because that’s what helped ME earn six figures from my blog within a couple years. And I’ve invested in plenty of Pinterest courses and other blogging courses (all created by other successful women entrepreneurs I might add) and they helped me grow my business a TON. I don’t know, this post just gave off major gatekeeping vibes to me.

  13. Thanks for this post, Kate!

    I recently started my own business (and I have a blog, too) and this post was really helpful. Personally, I struggle a lot with perfectionism, especially when it comes to creating content for my own blog. I’m one of those people who sometimes don’t post for months, because I take so ridiculously long to finish a blog post! I really want to change that, though, and I plan to post more regularly in the coming year. Strangely enough, it doesn’t get in the way at all when I’m creating content for a client or employer!

  14. I can totally relate to many of the points you make in this post. As a new blogger I’ve definitely spent way too much time focusing on things that don’t matter. At this point, I make exactly zero dollars from my blog, so I haven’t come across any of the financial issues yet, but this post really helps put things in perspective. Can’t wait to read the next posts in the series.

  15. Awesome post, Kate! I’ve followed many travel bloggers for short times but stuck with you precisely because of your originality, amazing information, and fun writing style. You always feel like a far away friend that I could catch up with any time and one with whom I’d love to travel. I’ve been fighting the office boys-club for decades and am finally now learning to speak up and ask for what I want, and I’m actually getting it! I’ve always had a dream to travel more and write about it regularly, though life gets in the way more than I’d like. Keep up the amazing travels, writing, and telling it like it is!

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