ll archives: 22 Things Ladypreneurs Should Do in Their 20s

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On August 22nd 2015, I turned thirty. “Dirty Thirty because the thirties–are–dirrrtyyyy!!!” was mentioned to me while celebrating that fateful Saturday night and seemed to be the consensus of the birthday calls and text messages I received throughout the day. Truth be told, I’ve been looking forward to thirty since like, twenty-two. Thirty was going to be the mecca of my young adultness. My shit was finally going to get together. I’d be an empress.

Aren’t expectations cute? I’ll let you guys know the outcome next year.

In the meantime, why am I listing twenty-two things ladypreneurs should do before they hit Dirty Thirty? Twenty-two is significant to me because it’s the age I fell in love with this ladypreneur life I lead. By way of a literally, life-changing editorial internship, I tasted “freelance,” I wanted it, so I made a way. My after-college work life has consisted of me part-time jobbing it, freelancing, founding things and fucking up. You have no idea how many business names I’ve gone through, Gmail addresses that I can’t remember the passwords to or the amount of “good ideas” my corporate, more structured friends have thankfully shot down.

BUT ladypreneur life is love. And as such, it’s just as complex. You’ve heard “love hurts.” Go ahead and replace “love” with “entrepreneurship.” One day you’re over the moon because you just landed a great client, you’re a boss, it’s summer... The next, you’re stricken with nausea, grief and insomnia over some other work-related issue that YOU, boss lady, have to deal with. Your real-job-having friends may have to Venmo you $50 bucks so that you can eat for the week, so find good friends (oh yeah, because money from your real-job-having parental units is a “no” as they’re wondering why you don’t “clock in” in the first place). You’re probably not going to New Orleans with the crew in November, so sit down. And most importantly, you’re going to have to put up with some amount of bullshit to do what you love. I’ve dealt with this in the form of corporate boyfriends unclear on why my laptop is and will always be the third wheel, too-damn-demanding pro bono clients, etc.

And so, dear twenty-something ladypreneur (or soon-to-be), here are twenty-two things I’d have told myself at twenty-two when I was gushing about working from coffee shops with my internship Editor:

Open your mouth and speak

You’ll have to do a lot of talking to people to make shit happen in business (and life) so you should do it well and do it often. Learn what makes people tick so that you can communicate what you want or need in a way that speaks to them.

Hone your hobbies

If you randomly love taking pictures and people are always like, “Hey! Great photo! You should be a professional!” Pay attention. There could be some entrepreneurial energy there. And that's almost exactly how this ladypreneur got started.

Know that you’re getting into risky business

We all jump into this because we love something and do it well enough to sell it. Passion is our driving force. In the beginning of a new venture, step away from your passion for a sec to review the business side of things. What are your risks going to be? Be honest and thorough. Ask ladypreneurs in your field about their experiences. Make sure that you’re 100% ready to leap and possibly crash.

Learn to apologize

Sometimes you’re going to be wrong about stuff. It’s fine. Acknowledge it and keep it moving.

Make good connections and keep them

Collaborations can happen in mysterious ways. I met Melissa Alam on Twitter, worked with her on an event in Philly and definitely crashed on her couch during my stay. This is why I love ladypreneur camaraderie.

Learn how to “PR” things

As the saying goes (and as we posted on Instagram on Sunday, are you following us?), you can catch more flies with honey than vinegar. When the going gets tough, be sweet. I call this practice “PR-ing” things. It works on most people and in most situations.

Understand that you’re going to get what you put out

This is true in all things, so be generous.

Know your values and boundaries

You will love and appreciate your ladypreneur lifestyle so much more if you know your worth and you’re clear on what’s OK with you and what is not. Communicate that to potential clients, collaborators, vendors, etc.

Know that change is constant

I hate most of everything I designed in 2009, 2010, 2011 and a little bit of 2012. And thank God because it was horrible. Change is good, even if it sucks at first. Also, we don’t have a choice in the matter.

Stop apologizing for everything

You’re actually not even sorry. Stop telling people that.

Be an ambitious realist

See all sides of every situation and work damn hard for the outcome you want.

Move towards balance

In Ladypreneur We Love interviews, we always ask founders how they balance work and life. You’ll notice that most of us have no clue really, but we are constantly working on it. Always be working towards finding balance. Without it, you only have excess. And excessive amounts of anything can lead to bad things.

Work for free

When you’re just starting out, this is kind of a must. You’ve gotta build that portfolio! In the beginning, the hardest part is choosing who is the right fit for you. You don’t want to get stuck doing what you love for someone you hate and for free. The lines start to blur. And nobody likes blurred lines. As you build, use your gut to guide you.

Know when it’s time to quit

If you’re like me, you like to win. You probably think one doesn’t quit if they’re a winner. Well, I’ll be the first to say, go ahead and remove that idea from your business brain now. Sometimes you’ve gotta ditch the zero for the hero.

Here are some examples of zeros:

A low-selling product A never-chosen service An un-read publication A shitty staff member An ill-matched business partner

Bye, zeros.

Don’t spend all of your money on cheese, charcuterie and vino – otherwise known as frivolous shit.

Yeah, so those are my favorite things. But as Hodgepodge Coffeehouse & Gallery owner, Lynne Tanzer puts it, “Buy the shoes from Payless now and get your Louboutins later.”

Date someone who understands your kind of crazy

I mentioned before that my laptop is always going to be a third wheel – that’s crazy. Find a partner who can understand and tolerate appreciate that.

Find good friends and find a good mentor

Friends. You’re going to need them. Like, really, really need them. You’ve seen us throwing around the term “business bestie” a lot at Ladypreneur League. Go get some of those. These are the people who will wholly understand why you’re not going to NOLA in November and share with you where they wish they could go. They are also the people who can meet you at 2 pm on a Tuesday for a Wine & Work session. Your corporate besties? Gotta have ‘em. They will give you sound advice based on their structured lifestyles – which is always interesting to hear about because it’s so different than yours. They’ll keep you motivated to continue ladypreneur living (because chances are they’d rather be at your house at 2 pm on Wine & Work Tuesday instead of inside their cubicle. You know, until you need the $50 bucks from them for the groceries). You know what else is motivating? Having a mentor. You should definitely seek a mature, successful ladypreneur to help you navigate the jungle of business ownership.

Pretty much expect to feel “fucked over” at some point

It sounds harsh, I know. But it happens. People will steal ideas from you, words, photography, money, maybe even your business if you don’t protect yourself. So get comfy with contract agreements and always be thinking of how to get ahead. I’m sure every entrepreneur has a “the first time I felt fucked over in business” story and probably many more stories like that one to share.

Don’t take business personally

We’ve all heard the term “it’s just business.” In the beginning of all of this, I hated hearing that. I thought it was a cop out for doing shitty things to people in the name of business. Now after having made some “it’s just business” decisions – guys, it really is just business. The decision maker is literally thinking about what’s best for the business. Will people be affected though? Absolutely. Could some feelings get hurt? Yes. So I think it’s best to:

1. Try to think about the intent of the decision maker. If they are purposely fucking with you or have made a decision based solely on their personal gain, that was a bad match anyway and they are unprofessional. Good riddance. If they are honestly doing what they believe is best for their business, try to be understanding. Emotions may still be a factor and that’s OK. Just decide that your next move should be your best move in the situation.

2. Unless they are somehow invested in it, do not let someone else’s feelings determine how you run your business. You don’t owe anyone anything. Using the words of the great Missy Misdemeanor Elliott, ask said feelings-haver, “Can you pay my bills?”

And because my ladypreneur lifestyle could have been so much easier had I started it on the right financial path, I’ve asked our resident finance expert, Victoria Penn, to share a few money to do’s:

Start an emergency fund

It may not be easy, but even if all you can afford is $20 a month, tuck that away in a savings account for emergencies only, and by emergency I do not mean that trip to NOLA or a can’t-miss deal on a vintage handbag.

Beware of the debt snowball

Both with your personal finances and your business, don’t get in over your head with debt. It can get completely out of control, and unless you like the sound of bankruptcy or a completely jacked up credit score, you will have to pay it back.

Start saving for retirement

It’s never too early to start your retirement savings. So go ahead, hop to it!