4 Things I’ve Learned From My Most Successful Female Friends

The best advice for slaying self-doubt and getting shit done

Last week, as we sipped tea at the brand new San Francisco location of the woman-centered co-working space The Wing, Meg and I waxed poetic about how lucky we are to be in the unique position of almost only ever dealing with women in our professional lives. (Occupational hazard of the wedding industry.) Obviously working with men is Not A Bad Thing (or doesn’t have to be), but having escaped a toxic old boys club career in favor of a female-led industry reminds me of the best parts of my formative years: kicking ass and taking names on all-girls teams. (Fun fact: my Odyssey Of The Mind team ranked second in the world. Brushes dirt off shoulder.)

Or basically, this:

A black and white comic illustrating "Why Female Friendships Are Important"

Having a powerful squad of women to build us up, give advice and feedback when we need it, and support us through TheHardStuff™ is one of the best things about being part of the APW team. Every year I’ve worked here, I’ve walked away feeling like I just got the world’s best mentorship. And over the years, I’ve amassed a working guidebook of advice from some of my smartest, most successful female (and gender non-conforming) friends and colleagues. And today, we’re partnering with Squarespace to share some of the sagest insight from these wise humans.

A woman in a brightly colored plaid shirt with red nails holds a pink postcard that reads "No one is waiting around to hand you an awesome mothaf*ckin life. Get out there + make that shit happen.

Squarespace has been a champion of our female entrepreneurship series and women-who-hustle content since 2014 (which is basically a century in internet years). And one of the reasons we love them so much is because they make it super easy to shout your accomplishments and share your worth online. They’ve got beautiful website templates and a platform that’s so easy to use we literally built The Compact on it in a week. (I’m a big fan of their standing risk-free 14-day trial, plus that 10% off for all APW readers you’ll see at the bottom of this post.) Because for me, almost every holdup I’ve had in the past when I wanted to put something new out into the world was “Okay, but how do I make a website?” (Which is why my college blog never made it past the URL stage.) So anything that removes roadblocks on your way to world domination gets my approval.

So with that, here are the best bits of advice I’ve gleaned from my most powerful female friends that you can apply to your life, your career, and your website:


We’ve been working with APW’s business coach, Jay Pryor, for the last few years (they were born female, transitioned to male at age thirty-five, and currently live as a gender nonconforming person. So even though they are not female-identified, I’m making an exception because Jay always has the best advice). And the wisdom we’ve gleaned in that time has been transformational to our business. But one of my favorite philosophies Jay espouses is to practice constant forgiveness. With others and yourself. It sounds easy enough. But usually my creative process looks like this.

A black and white comic illustrating "Failure: How to deal"

Whenever I bring up constant forgiveness to an overachieving type-A friend, they sort of roll their eyes at me like I’ve just suggested using healing crystals to fix their car. So when Meg brought up the concept of the sunk cost fallacy at a meeting the other week, it gelled Jay’s concept into something more tangible and economically focused for me. It’s really easy to convince yourself to put more time and energy into something that’s already stolen a ton of time and energy—even when it’s not working—because we’re convinced that the payoff will mitigate the cost we’ve already put into the project. For women, I think this is compounded by an inability to let ourselves off the hook when something isn’t working. And it can prevent us from moving onto bigger and better goals.

Putting it into action: How many of us started a website on an old platform five to seven years ago, and even though it’s super not working anymore and looks hella dated, are sticking with it? (It’s fine, even we’re guilty of this at APW. Don’t ask me how many times we lamented having to build a new site from scratch because we just rebuilt that old one and it was so expensive.) Well, you officially have my permission to give it up.

One of the reasons I like working with Squarespace is that the platform is incredibly flexible and they are always updating the software to be more user friendly (with tons of user-friendly perks like a free URL with your subscription, and beautiful free stock photos from Unsplash). But even more important? You can change anything about your website at anytime. So in the more likely event that you pick a template, do a few hours worth of work on it, and then realize it’s not a good fit after all, you don’t have to throw out the baby with the bathwater. Changing a Squarespace layout is a matter of swapping out your template. Which is at least one way to mitigate the sunk cost fallacy. But the other is to just give yourself permission to move on from whatever you’ve done before, and start from scratch. #NoShame.

If you’re doing it right, you should make people feel slightly insulted

I am guilty of making myself smaller so that other people can feel big. I never want my colleagues to think I’m trying to take credit for their work or idea. But I love the advice Meg gave Najva in her website critique last month: your website should always make people feel slightly insulted. Now, I’m not advocating that you should tell all your old high school friends that you invented Post-its. But if there’s a nagging part of your brain that is telling you maybe you don’t actually deserve credit for that accomplishment simply because you didn’t do it alone, you should claim it anyway.

A page from Najva Sol's Squarespace website with a picture of her surrounded by a bright balloon installation, as shown on a computer monitor

In fact, I was just browsing the internet for wedding planning resources, and I noticed someone described themselves as the number one wedding planning resource for couples on a budget. At first I was like… ’scuse? I thought that was our jam. But then I was mostly impressed with this person for staking that claim. Good on them. (Also, reminder to us to stake it, but for real.)

Putting it into action: If you’re trying to put together your resume, or create your online portfolio, don’t temper your accomplishments with modesty. And whatever you do, don’t hide them. Most of Squarespace’s templates are pre-designed with a prominent front page and lots of opportunities to plug in what you makes you special. So use them. If someone has to click through several menus to get to the thing that makes you shine, you may have already lost your prospective client or employer.

But beyond that, don’t be afraid of what your colleagues or competition think of your website. Barring Theranos levels of deception, you’ve earned a right to tell the best version of your story. And if you ask around (or just ask your most Meg-like friend), you’ll probably find that you’re underselling yourself already anyway.

You have to ask for what you want

I know, we’ve heard the adage a thousand times, you don’t get what you don’t ask for. And to me, it always feels like very 1987 Michael Douglas advice. But when we invited the brilliant Cyndie Spiegel to give a talk at The Compact last year, she broke down the myriad ways women undermine themselves everyday. Stuff like not asking for restaurants to accommodate food intolerances because it might be an inconvenience. Or living with discomfort because you don’t want to be a squeaky wheel (lemme tell you about my guilt for asking our new building to increase the temperature in our office to something greater than fifty degrees).

So one of the best tips I’ve gotten is to start small with your requests. For example, my local cafe never puts out whole milk on their bar. And as any self-respecting person of British heritage knows, tea is meant to be consumed with milk. So every day, I poke the barista and politely ask for whole milk for my tea. It’s a very small act in the scope of things, but getting a small yes emboldens me to go for bigger asks. (I’m sure there is some brain science behind that.)

A page from Cyndie Spiegel's Squarespace website that reads "I'm on a mission to empower 100,000 women to live more boldly by the year 2020" as shown on a computer monitor

Putting it into action: It’s really frustrating when I have to play detective trying to figure out what someone’s goals are on their website (again, when Squarespace makes it easy, don’t make things harder on yourself). What kind of work do you want to be doing? What kind of client is your dream client? You have to ask for these things or no one will know how to deliver.

One of things I most admire about Cyndie is how she lives this principle in her own business. If you check out her website (hosted on Squarespace, just sayin’), you’ll see a big, bright claim that Cyndie is “on a mission to empower 100,000 women to live more boldly by the year 2020.” Y’all, that is huge. That is brazen and bold and a big ask. But guess what? It immediately makes me want to make it happen for her. So by the very nature of daring to ask for it, she’s already increased her chances of getting it.

Nothing will make you feel better than doing the work

Okay, so Jordan is technically Meg’s friend, but I’ve hung around her enough to know that she always comes with the good advice. When she was launching The Color Factory in New York last year (a hugely stressful and complicated project with lots of moving parts and too many city permits to count), she spoke often of how her favorite mantra is nothing will make you feel better except doing the work. And it’s become one of my favorite personal philosophies.

Hands hold a sign that reads "Nothing will make you feel better except doing the work"

When I’m plagued by anxiety and a mounting to-do list, I often get stuck with analysis paralysis. I don’t know where to start because there’s too much to do, so I just sit there and worry, doing nothing. And the longer I push it off, the worse it gets. Before long it’s nearly impossible to start. But I learned something important last year when we were launching The Compact: analysis paralysis is often just perfectionism in disguise. I set an incredibly high bar for myself, and then get scared I might not meet it. So I freeze.

Nothing feels better except doing the work means that I can give myself permission to start something without any pressure on the finished product. Trash first draft? No problem. Imperfect craft project? Great. You can (almost) always change something after you’ve started. But you can’t fix never starting at all.

Putting it into action: While you might not have a professional artist husband to paint you a sign of your favorite mantra (see: above), you can put it on a Post-it on your desk and get to work. I’ve seen so many women talk about starting a website, get overwhelmed, and then never start. But there are a ton of small steps you can take to get your momentum going. Create a free Squarespace account, pick a URL (it’s only $20 to reserve one, or free if you create a subscription), browse templates, make a logo, insert some free photos, and see what you like. Play around with the technology just for the sake of figuring it out. Just. Do. The. Work.

One of my goals for 2019 is to spend more time in the company of badass women (hello, Compact 2019). And in the meantime, my takeaway from all of the above is that the secret to world domination is little steps, one foot in the front of the other, and never losing sight of how far you’ve already come.

What is the most powerful advice you’ve gotten recently? what are you struggling with right now that you could use a pep talk about?

Squarespace logo

This post was sponsored by Squarespace. We are thrilled to be continuing our partnership with Squarespace talking about what it means to be a woman with #goals in this modern world. Whether you’re stepping up in your career or striking out to do your own thing, one of the best things you can do for yourself is create a place online where you can show off your work in the form of a portfolio site, an online resume, or another hub that displays just how awesome you are. Squarespace provides an all-in-one hub (including everything from custom URLs to beautiful templatesanalytics, and now even built-in email marketingthat makes it easy to build your online home beautifully, even if you’ve never made a website before and have no idea where to start. Click here to get your website started today with a free 14-day trial from Squarespace. APW readers get 10% off your first Squarespace purchase when you use the code APW19 at checkout.

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