SellingYourselfI get extremely motion sick. Literally, in anything that moves. Bus, boat, airplane, New York City cabs, regular cars (sometimes when I’m driving), and yes, even the train, that gentle old aunty of land travel. Some people take lip balm with them when they leave for the day; I pocket a few loose Dramamine. In fact, I need to take one sometimes just to plan my travel.

And yet, I go places anyway. I’ve taken a bus around rickety hairpin turns in Israel, a leisurely riverboat cruise through the Netherlands, and even a cruise through the Greek Islands (though I almost lost it all at the blackjack table, and I don’t just mean my chips).

I know plenty of people who get the same head-spinning, gut-churning nausea at the very notion of promoting themselves. It’s true.

Guess what? Doesn’t mean you don’t have to do it. Any more than I can get somewhere in real life without moving. I find ways to make it palatable, even enjoyable (yay drugs!). If I said, hmm. I’d like to avoid nausea at all costs, so I guess I won’t leave my house, well, I wouldn’t have much of a life.

And you can’t have much of a business, brand, or career without being able to tell people why YOU—why someone should listen to you, bet on you, invest in you, choose you.

Here are the three things people say to get out of selling themselves:

“But…testimonials! Can’t other people say it for me?”

Testimonials have their place. We all want third-party reassurance. But that doesn’t mean you get to go mum about who you are and what you offer.

“But…my work/reputation/experience speaks for itself!”

It stands for something, no doubt. It’s incredibly valuable. Your brand is in part what you’ve done, but also what you say about what you’ve done. It’s also your brand PROMISE—what you will do, deliver, create for the person who invests in you. Do you know what this? (Sorry, “great service” doesn’t count.)

“But…I don’t want to be salesy. It’s not who I am.”

The words “salesy” and “sleezy” sound suspiciously similar. It’s a shame that a few bad salespeople and sales tactics have spoiled the lot. Fact is, anyone who’s not in sales tends to, well, hate sales. Or think they hate sales. (Even some of the people who make their LIVING in sales think that.)

So, forget sales. Think of it as something you have no problem being: A better, clearer, more compelling communicator. Why wouldn’t you want to do that?

There’s one surefire cure to alleviate the nauseating effect of trying to put yourself “out there”:

Know what makes you different, and worth knowing, and share it from a place of giving, not getting.

Simon Sinek has famously said, “People don’t buy what you do, they buy why you do it.” Yes–100 percent.

But you also need to know how to explain to someone why they should choose you, based on who, what, and how you can help them, make their lives easier or better than they were before.

Do you think a first-grade teacher is worried the kids in her class will think she’s trying to “sell” them on reading? Of course not! You better believe she has to sell it. She has to make it appealing and fun and worth doing, to reward them for it, because it will change their lives.

That’s what you have to do. Get outside of your head, your ego, your fear, and focus on That One Thing that you know you can deliver, something the other person cares about (not just you).

Put THAT into words. And you’ll never loathe the “Why you” question again.

I’m about to launch my first-ever virtual workshop on JUST THIS TOPIC. It’s called the Why You Workshop, and it’s running for three consecutive Wednesday evenings: 8/10, 8/17 & 8/24 @ 7:00 p.m. ET. It will be held via phone (low tech!), and the calls are recorded (so you don’t have to be live on the call).


….Now, do I feel nauseous about the fact that I just asked you to check out something that I’m selling? That I just promoted a thing to you? Meh. Mild, tummy rumbling, but that’s ok. We should always have that inner gut check. After all, I had to get over this fear myself!

But I’ll tell you this: This work, helping people figure out their thing, which I’ve previously only done 1:1 with my clients, has been so rewarding and helpful, for me and them, that who am I NOT to tell you about it? It’s what I do, and I do it well. What am I going to do? Sit on it and hope you ask me about it? You won’t! I have to say it.

So I just did. And you can do the same thing in your business.

If this strikes a chord in you, seriously, sign up now—the calls include live Q&A and on-the-spot laser coaching and walk you through this process to land the right positioning. You’ll not only feel more confident every time you explain what you do…you’re less likely to lose your lunch or suffer fits of dizziness, loss of vision, you know. The usual.

Join me and get yourself a hot seats while they’re…still hot!


fistWhether you work for yourself or someone else, there’s one thing I know about you: You want your work to matter.

Even, or especially, if you’re afraid it doesn’t. Maybe your boss or clients heap praise on you. Maybe they don’t say a damn thing.

But you want it to be good, and you want people to notice it.

I just spoke at How Design Live (#HowLive), the largest design conference in the country. Five hundred people came to my session, entitled “Build Your Personal Brand On the Job,” most of whom were sent to the conference by their employers. But while that’s a catchy title, what the talk is really about is how to get your work to matter. Because when you do that in a way that’s uniquely yours, bam. You have your brand.

Because the point of having a ‘brand,’ a word that’s becoming annoying even to me, is so that people know what you stand for, what to expect, and why they should bother with you. Your brand connotes meaning, that is the point. And one way to make sure you mean something is to make what you do matter to other people.

Three ways to starting doing that:

1 – Think like an entrepreneur.

And by that I mean, stop making someone else responsible for what you do. Stop checking boxes with the hope that it’ll all add up to something, and decide to take the reins of your career. An entrepreneur, by definition, doesn’t wait for someone to say ok. They just DO. What can you go out of your way to do that would create more meaning, more value, where you are? You decide how you’re going to make things better around here, and be the one to make it happen. What are you waiting for? Initiators get noticed.(More about what makes a true entrepreneur.

2 – Give gifts.

Go above and beyond to give things you don’t have to, and you will delight, impress, and show that you are more than your job description. I don’t mean a fruit basket. I mean a piece of added value, an extra thing, a bonus, a bit of insight. Something of value to the receiver.

Ken Carbone, co-founder and Chief Creative Director of the Carbone Smolan Agency said that when he’s bidding on a client, he always gives them something valuable for free—in his case, he says, “$100K worth of branding advice,” and it’s something so valuable he had it trademarked: His “unify, simplify, amplify” approach to creating a more powerful brand. Would you forget that guy? Not me.In his book Linchpin, Seth Godin writes, “The gift represents effort. Effort is separate from money, separate from job description, separate from capitalism itself.” You achieve the goal of being indispensable, he says, “by giving selfless gifts, and those benefit everyone.”

3 – Don’t wait until your next job interview to figure out what you were doing there.

How many times have you scrambled to cobble together a great answer to use the next day at an interview? Because you know they’re going to ask about your last job. Or maybe you’re struggling to update your Linked In profile, and aren’t sure what to say.

Don’t wait until your ‘done’ with a job or role to figure out why it mattered. Think about it now, while you’re doing it. The beauty of the Linked In profile is that it’s fluid and evolving, unlike a resume, which is outdated the moment you print it. You should ALWAYS be updating your profile—with new projects, new insights, new skills.

Here’s a tip: If your profile or resume reads like something I could post on a job board tomorrow, then you’ve written a job description, not a record of your contribution. Make sure that you show not just what you did, but what effect it had, and how what you did mattered. After all, if you don’t know, how will anyone else?

…Not sure what your brand is or why what you do matters? Maybe you need some help. I’m launching a live, online workshop this summer called “Why You” — it’s not up yet but it will be. Be the first to sign up (and get a hot seat, which means you’ll be in the spotlight) by adding yourself to my list here.)

Man jumpLet’s face it: There’s nothing sexier than describing yourself an an entrepreneur. It’s like a hot leather jacket that everyone is trying on for size, including me. If it’s not a fit, maybe you like this simpler style, called solopreneur. Or maybe this tiny little handbag, called micropreneur instead. Or, this briefcase-slash-diaper bag called “mompreneur.” If you’re an entrepreneur looking for commercial premises, makes office rental easy.

Point is this: We are bending the term to make it mean what we want it to, need it to. I defined myself as a solopreneur, even had a video show and podcast by that same name…and then Grant Cardone called me out on Twitter and was basically like, that term sucks. “It’s too small.”

He’s right.

(And forget freelancer. Don’t get me started on what a horrible term that is.)

So what IS an entrepreneur, really? An editor at Shopify reached out to me to ask me what I think (and he wrote about it in this thoughtful piece here).

Fact is, there is one definition of it, and it’s this: a person who operates/runs a business, and takes on considerable risk to do so. If you need help making your business venture a success, take a look at how WHITEHAT SEO could help you. Traditionally, we think of the entrepreneur as a person who finds and exploits a need in the marketplace, and either invests his or her own money, or more likely someone else’s, to fund this vision, product, service, company, and if it goes well, everyone makes a ton of money. It traditionally entails hiring people and renting office space and negotiating big pricey deals with vendors, etc. The hiring people part can be difficult, but the hardest part is managing your payroll effectively after you have chosen the right people. Fortunately, Cloudpay is able to do this, even if you are a global enterprise.

You May Be One Yourself

Fact is, entrepreneurship has changed so much in the past decade that you may not do any of these things. You may never have an office or a staff, you may never raise funds from investors or regular people. But chances are you, don’t do this all yourself. All you need is a laptop, an internet connection, and a bank account to do business and rightfully call yourself an entrepreneur, and many do.

So if I am going to take liberties with the term, or at least tease the nuances, I would say that an entrepreneur is less defined by the business she runs or the amount of money they raise, and more defined by vision, risk, and character.

An entrepreneur leads with the solution to a problem, not with just a need to make money. An entrepreneur doesn’t just “organize” a business in my mind, but fuels it, directs it, and creates it. I hesitated to call myself an entrepreneur for a long time because I thought you had to have a Harvard MBA. I was so wrong.

Entrepreneurs are: scrappy and disruptive, creative and unruly, strategic and unstoppable. Sometimes they make lousy students and difficult employees. Some literally propel themselves on the force of their personality and the appeal of their promise, and other people help them carry it out and make it happen.

I’ve heard more than a few people say that entrepreneurship means “freedom.” I don’t know that I agree with that as the defining element. Maybe you don’t want debt. You know who else doesn’t have debt? A homeless guy. Is that what you want? You know who has a lot of freedom? An unemployed person. There are lots of ways to be free, and in fact, taking on the risk and investing yourself in something the way an entrepreneur does may be exciting and empowering, but “free” is not what I’d call it.

You’re free of the constraints of a corporate job, sure. That’s what people love. Look, we live in the land of the Lone Ranger. We love the idea of this rabble rouser, out conquering a new frontier. That’s romantic, and yes, many entrepreneurs slave away in solitude. But plenty don’t. The smart ones never dream of doing it on their own.

The entrepreneur is a maestro, a leader, but knows the value of team, too, and can lead and inspire. To my mind, I am not so hung up on the “prerequisites” for being an entrepreneur. Because I believe most can’t help themselves. And that’s why they do it.

In this way, they’re more like artists: They are compelled to make, create, connect—and that is why we are in love with them, aspire to be one or be like one. I can’t think of a better reason.

So. Is that you? I’m thinking I’m liking the fit myself.

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…By the way, if you DO dream of pursuing a business idea and becoming an entrepreneur, check out the Creative>>Founder Lab at NY Media Center. They’re accepting applications now for their 8-week intensive running June-July 2016. I’m one of the instructors, leading a session on vision and mission, which I’m psyched about. Check it out!

You and I have fallen under the sway of a misled idea: that in order to advance our careers, we must persuade people to recognize our worth and then convince them to pay it. When negotiating salary or figuring out what to charge for a service, the first question we often ask ourselves is: What am I worth?

But that question disempowers you.

It calls into question something personal that goes beyond the actual value of your skill or service. There’s also a dangerous connotation — particularly for women — that links price with love or acceptance. (“If you like me, you’ll pay what I’m asking. If you don’t, you must not like me because I’m not good enough.”) It’s a slippery slope and ineffective.

Instead of asking “what am I worth” or “am I getting paid for what I’m worth,” the question to ask is: “What are my products or services worth to this person right now?” In other words, what will the market bear?

For years I struggled to reconcile what I thought I was worth with what I was getting paid. At one point, all I wanted was $40K. I believed that was where I needed to be and that I was worth it (damn it). It killed me when the company told me they couldn’t do it. I went down the rabbit hole: Am I not worth that?

The magazine was in the red! They couldn’t pay the bills! It had nothing to do with me. And I needlessly made it harder on myself.

The turning point for me was a recent episode of my show Solopreneur. I interviewed Ilise Benun, founder of Marketing Mentor, who has been helping creative professionals go into business for themselves for more than two decades. “My clients always ask me, ‘Why can’t I convince people to pay me what I’m worth?’” says Benun. “This is the wrong question, because it sets this up as a pricing problem, which it isn’t. It’s a marketing problem, and it has a marketing solution.”

The key, says Benun is to separate what you do for other people from what it means about you. In other words, take your ego out of it. This blew my mind, and the doors off everything I used to think about rates and salary.

It was also a huge relief because I’ve spent too much time worrying that either I wasn’t worth much, or I was so good no one could afford me. “The conflation of personal worth with professional acumen is also very childish,” adds Benun. The “love me daddy” approach to winning business infantilizes you — it treats the proposal (or salary or raise) like an allowance, one that you “deserve” because you were a good girl. Ick.

Don’t use worth as a determiner of value or price. Your true worth doesn’t have a price, so stop wasting time trying to appraise it.

Want more? Watch this episode of #PowerLunch, my weekly webinar for entrepreneurs with an appetite, where I talk about when and how to work for free (and get something great out of it).

DanielDiGrizDaniel DiGriz is so smart that after a few minutes of listening to him, you can actually feel yourself getting smarter. Now that is a gift. (Let’s hope it worked.)

The founder of Madpipe, author of All Marketing Is Dead, and self-titled “digital ecologist” (a term he’s had trademarked) has lots of titles, and believes everyone should have a bunch, too, since all social media sites (including LinkedIn) are search engines. Oh, and also because titles don’t matter.

A word about what exactly DiGriz does: He helps clients become thought leaders and create a successful marketing presence in their space—which changes depending on the company. As an external marketing director, he does this through one-on-one coaching, supervision, and training of in-house teams to meet their own marketing needs, which are unique and different from everyone else’s.

Rule #1 of Thought Leadership: Get Over Yourself

The biggest mistake of thought leadership, he says, is this belief that the onus is on everyone else to come to us, read our sites, care about us and what we have to say. In fact, this isn’t about you at all, which is why DiGriz doesn’t spend all that much time talking about himself. It has to do with how you change the world.

“What you are isn’t relevant,” he said. “This is one of the first lessons of thought leadership: It’s not about you. It’s about…what creates a response in the end user.”


Click here to watch interview.

Rule #2: Have An Original Idea

Anyone can be a thought leader, says DiGriz. But thought leaders don’t say, “Yeah, what she said!” You have to have a fresh take and original ideas and insights about the industry right now, and how to make things better.

Knowledge after all, is replaceable, he says. It’s why he doesn’t mind sharing it freely via his blog, his podcast, what have you. Experience, however, is not. And the mark of a pro, he says, brings all of that experience to the table with a defined, intuitive skill set.

Rule #3: Know the Difference Between Being in Charge and Owning the Conversation

Another misconception (and an arrogant one to boot) is that whether you’re in charge of a big company or work for yourself, you’re “the boss” and that makes you important. You’re not the boss: The economy is. That ground is always shifting beneath you, and your success depends on how you can adapt to it.

Which brings me to his book, All Marketing Is Dead—because in fact, he says, it is. And this is where a discussion about marketing becomes one about mortality: Because what holds in the Walking Dead is true for business owners: Traditional marketing tactics, even as we use them, are zombies: stiff, slow, awkward, easy to outrun, consumed only with feeding themselves, and must be killed on the spot.

But that doesn’t mean marketing is going away, or that you or I are in any way above it. If you try to excuse yourself from marketing and all its aspects (social media, outreach, etc), you quite simply aren’t a business owner. In other words, marketing is not a tap you turn on when you need it, but a consistent effort, one that you should make for yourself just as you would if you had thousands of shareholders to answer to.

Thought leaders know this, and thus must continue to adapt and update their efforts, annihilate the stumbling zombies from their strategies and instead find ways to make their marketing elastic, intelligent, human, integrated.

To be a thought leader, says DiGriz, ask yourself: “How can I make the world more effective, raise the bar in my industry and improve the way I communicate about it?”

“You can be a thought leader, introduce new concepts and ideas without getting anyone’s permission. If we can do that, we can lead in our fields, change our industries and grow our business together.

(Watch the full interview with Daniel DiGriz on Solopreneur.)

(Also check out DiGriz’s podcast—on this episode, he had me on to talk about why brands need a spokesperson.)




Screen Shot 2015-04-20 at 9.30.20 AM

A colleague of mine, Michelle, was launching her own life coaching business and wanted advice. So I spent some time on the phone with her one quiet Friday afternoon and told her all the things I thought she needed to do to make her offerings more clear, unique, and benefit-oriented. I went through her website, her mission, gave her insight into how to think about content and social media. This, after all, is what I do. And I’m paid well to do it—but for Michelle, I did it as a favor.

She listened intently and while she put up some resistance, she said she knew what I was saying made sense. She had her work cut out of her, but she seemed, at least to me, to understand what she needed to do.

Then a mutual friend of ours told me she had been asked to lunch by Michelle, who wanted to pick her brain about her business. And she told her essentially the same things I had. And then another friend mentioned she, too, had been approached by Michelle, weeks later, and was asked the same set of questions over again. And that, in fact, she hadn’t moved forward on any of what we’d told her.

The Advice Trap

This was when I realized that one of two things was true: One, Michelle was addicted to advice and used it to procrastinate doing anything at all, or two, she didn’t actually want advice, but was seeking approval.

Both scenarios present a serious problem to the business owner, and if you ask me, it was likely a combination of both. And while it’s always a great idea to consult with a set of trusted colleagues and friends, it becomes another thing altogether when you become a professional advice seeker instead of decision maker.

All the information out there does not help, because you will never read all the books and websites and blogs. You will never “finish” the research so that you can come up with the best answer. I’ve done this myself. It’s a writer’s trick—and curse: to keep researching a story instead of writing it. It’s a great way to feel productive without actually doing the hard work of writing the piece.

The advice industry is rich with resources, but also can keep you on a spin cycle of advice consumption so that you become so bloated with ideas and information that you become unable to take a single step.

There’s only so many lunches you can go on, so many retreats and seminars and masterminds you can attend before your head explodes, especially if you’re not doing anything with what you learned. OK, so you went to a Tony Robbins’s event and walked on hot coals and felt you could do anything. Did you?

The other problem you might have if you’re addicted to advice is that you bleed colleagues dry of (often gratis) advice, and act on none of it—which is a waste of both of our time (and I also may be loathe to bother giving you advice again). Maybe you think it conflicts with what you should do. Except that you’re not doing what you should do, either! And so you continue to mine for insights, at great expense in time and often money, except instead of seeking an aha! moment, you’re hoping someone will bless what you’ve done and relieve you of having to push harder or change anything. And that’s a problem. Because asking advice “feels” productive, but it’s only productive if it helps you enact real change and challenge your own presumptions in your business.

Daniel Digriz, creator, a marketing consultant and one of the most intelligent, insightful people I’ve met, had this to say about advice that challenges what you think: “If you dismiss anyone who doesn’t agree with you, then you can never improve or learn, because what you’re saying is there can’t be anyone who’s smart who also disagrees with you.” Doesn’t mean you have to take everyone’s advice. But at least know why you’re asking, and be willing to question what you’re doing as a result.

There is no point in asking advice if you don’t let it inform, if not transform, what you’re doing, and I’m talking business, but life, too (how many friends have to tell you you deserve better than the person you’re dating before you believe them?). Note that moment of defensiveness, that nervy twitch that happens when you resist or dismiss an idea. And ask yourself, why, then, were you asking in the first place?

Here are a few questions to ask yourself so that you can get clear about why you’re asking so you can move forward. They only help if you’re really honest.

What to ask yourself before you seek out the advice

The act of writing out the answers to these questions makes them clear as day and hard to ignore, and will change the way you go into the meeting or event. It keeps you from falling under the spell of advice, thinking that just being around it will make you successful (it won’t).

  • What am I seeking advice about, specifically?
  • Why now?
  • Why am I asking this particular person for this particular advice?
  • What am I hoping to learn? Is it something different or new, or the same thing?
  • What am I afraid to hear?
  • What will I do if I don’t agree with what I hear?
  • Am I willing to follow advice if it conflicts with what I think?
  • What would happen if I did?

What to ask yourself after you’ve sought advice

Next, write out the answers to these questions so that you can do an honest evaluation of what you’ve heard and what you’ll do next.

  • What did I learn that was new?
  • What was familiar (and why haven’t I done it yet?)
  • How did hearing another’s insights make me feel (i.e., resistant, upset, confused, relieved)?
  • Why do I feel this way? (Be honest!)
  • How did I feel later, say a day after I talked to this person or attended this event?
  • What would happen if I put one of the ideas I learned into action?
  • Why will I, or won’t I?
  • Do I feel greater pleasure when I ask for advice, or when I receive it?

…That last question is key, because if you recognize that you feel optimistic or productive when in the process of asking for advice, but not after you receive it—and this is a pattern for you—then you are stuck in an advice-seeking cycle.

The fact is, advice seeking should be a process that energizes and focuses you. It can’t be this for you if you ask a zillion people and act on none of it. Be honest about what you’re looking for, and recognize, too, that advice in itself is worth nothing at all if it doesn’t inform and inspire your next step.


The lovely Shasta Nelson, author of Friendships Don’t Just Happen and CEO of the female friendship-matching site The lovely Shasta Nelson, author of Friendships Don’t Just Happen and CEO of the female friendship-matching site

The lovely Shasta Nelson, author of Friendships Don’t Just Happen and CEO of the female friendship-matching site 

Shasta Nelson is a relationship expert and the author of Friendships Don’t Just Happen. She is also the CEO of a female friendship-matching site called, which she created after recognizing that many of her life coaching clients were having a hard time finding meaningful relationships with other women. I recently had Shasta on my show, Solopreneur on the Whatever It Takes network, to talk about the importance of fostering deep connections and why they’re crucial to health and productivity.

In this episode, Shasta explains that while we live in a world that seems more connected than ever, most of us report not having the connection we want. She shares startling research about loneliness—it’s as damaging to our health as smoking 15 cigarettes a day, and twice as harmful to our bodies as obesity!

She also explains why it’s especially important for solopreneurs, many of whom are no longer surrounded by colleagues during the workday, to regularly take time out to interact with friends and contacts (it’ll not only boost your well-being, she says—it’ll also help your business).

Here’s some more about Shasta, why she thinks the fear of rejection holds us back from intimacy, and how she knew she was meant to connect people.

Do you have a day job?

I’ve been doing this for over 6 years but am constantly creating new “side jobs” under the umbrella of friendship such as coaching programs, international trips, retreats, and e-books.

What did you think you were going to be when you grew up?

A war correspondent on the news.  Then in college I decided I’d much rather be someone working to make the world a better place (preventing wars!) than covering them!

When did you realize this was (or wasn’t) going to happen?

In college when I felt excitement about possibly becoming a pastor.

What is it about your life now that you can’t believe you do, and wouldn’t believed if someone told you 5-10 years ago?

That I am in the middle of writing my 2nd book for a publishing house.  It was always a dream, but now to not only have done it once but to have the opportunity to do it again?  Awesome!

Where do you think most of us waste our time? What do you recommend doing to change it?

In the world of friendships, we waste a lot of time worrying about people not liking us instead of initiating and adding value to people’s lives in ways that build strong friendships. By fearing rejecting or taking everything personally, we miss out on the intimacy we most want!

What’s the worst advice you’ve ever been given (and did you take it)?

Anytime someone has cautioned me to stay the “same” out of their fear of what the “new” might hold for me. I’m sure I have heeded their fears at times but I’d like to think that for the most part, I have continued to take risks for the people, causes, and opportunities that I believe in.

What advice would you give yourself if you could go back in time 10 years?

Sign up for every workshop that will tell you more about yourself and take every inventory that will tell you how you’re wired so that you can benefit from this wisdom in as many ways as possible!

What lesson(s) did you learn the hard way (could be your career, or life in general)? 

That just having a good idea isn’t enough. I went into my business hoping that if people heard about my website that they’d sign up. Ha! It’s often a bit disillusioning to all of us that the process of growing a business often takes longer than any of us wish it did. Healthy expectations are crucial!

Any other advice you want solopreneurs/entrepreneurs to know? Resources you recommend or folks you like? 

Take the StrengthsFinder 2.0 inventory. And hire a coach who can really help you understand what that means for how you’re wired, identify your sweet spot, manage your weaknesses, and know where you most need help from others. If you don’t know any strengths coaches, my husband Gregory Nelson is one of the best! Secondly, figure out your Enneagram type. My favorite book on it is The Wisdom of the Enneagram.


For more about Shasta and her tips on how to nurture your existing friendships and jumpstart new ones, visit her website, follow her on Twitter at @girlfrndcircles, and pick up her new book, Friendships Don’t Just Happen!: The Guide to Creating a Meaningful Circle of GirlFriends.

Watch a new episode of Solopreneur every Tuesday at 4pm ET!

Screen Shot 2015-03-07 at 2.28.58 PMI’ve historically been loathe to question, let alone buck, rules and regulations. If the sign says “must be this tall” and I’m not, I’m out. If it says you need these qualifications, and I don’t have them, I pass (this is a big mistake, by the way). And when something warns me that what lies ahead is hard and not for everyone, I assume that everyone means me.

As a result, I have given other people’s judgments more clout than I should have. I assume someone else knows better. This has been the great awakening of my adult life: When I realized that nobody knows shit. Not really. And that I know just as well as any of them.

This came to light for me recently when I went skiing for the first time in 15 years. I had been a nervous intermediate skier in my teens and 20s, and when I passed beyond the age of annual school ski trips, the sport fell off the radar for me.

But when a good friend got three free nights at a luxury resort in Lake Tahoe, how could I say no. So I went! And within an hour on the mountain, I had my ski legs back (except for the knees; the knees did not come back). I felt reborn—and, interestingly, less scared than I’ve ever been in skis in my life. This I credit a little bit to yoga and a lot to age. I’m simply less afraid of things than I was.

When at one point during our clear, sun-filled day, my friends suggested we pass on Logger’s Loop, the blue intermediate trail, for the Chute, a black diamond, I girded my loins and prepared to be scared, which I’ve spent my life doing. But when I looked over the edge, I thought, hmm. Is that “really” a black diamond? Is it? And then I thought, who cares? What if I didn’t know what level it was at all, and I just…went? It’s not like the sign was the only thing I saw: The slope was right there in front of me.

Which made me realize this simple truth: I’ve devoted way too much time heeding warning signs instead of just taking on whatever trail is in front of me. The signs are meant to instruct, after all, not rule your damn life! It occurred to me that this mountain had been here long before anyone took a pair of skis to it, or started labeling it green or blue or black. That’s simply a human assessment of the trail. And guess what? Some are crappy assessments!

So down I went, slicing smoothly through the snow. I loved it. I managed perfectly fine and felt like a rock star. And it dawned on me that this wasn’t just about skiing. I have spent the better part of my life looking for signs that I couldn’t or shouldn’t do a thing, that it would be too big, too advanced, too hard: the black diamond college course, the black diamond job, the black diamond relationship.

(Side note: I was actually invited into the honors program at Boston College after my freshman year, which they never do, and I turned it down because I assumed they probably had it right the first time. It was probably too hard for me. I was wrong, and I regret it.)

It’s worth asking yourself where in your life you’re avoiding a bigger challenge because you assume someone else knows better, or worse, are busy enforcing your own self-constructed limits. Caution has kept me alive, to be sure, but it hasn’t helped me grow in ways that matter.

The only time I’ve really achieved anything I was proud of was when I challenged the limit or questioned the rule itself, and chose to do the thing that intrigued, thrilled or even scared me a little. That’s a black diamond moment. Seek them out. Take them. Because nothing compares with the rush you feel when you reach the bottom and look up at just how far you’ve come.

If you like this one, I promise you there’s lots more. Come on over for #PowerLunch every Thursday, 12-12:30pmEST, one Periscope and Blab