By Sara Rosso (VIP Global Services Manager, WordPress)

If you’re new here, you should probably read my biography just to give you a better sense of who I am. In short: I do a lot of stuff. I’m curious. I love learning. I take risks. I speak my mind. I dare.

The risks I take are reinforced by a belief that I owe it to myself to at least try. I’ve always seen myself as a bit of a Jack of all trades, rather than an expert in one subject, but I’ve come to believe that’s a blessing rather than a curse. Releasing myself from the aim of being an expert or being perfect at something means that I have the complete and utter freedom to try. And fail. Hell yes, fail. Even often!

But trying, definitely.

I’ve spent a lot of time talking with (girl)friends about what’s next for them. I mentioned that I wanted to have a Vision Board workshop for this reason (which had to be postponed due to crazy November travel for me) because I want to help them start to think about “what’s next?” without hearing “not until I...” or “maybe when I...” or “I’m not ready” or “after...” or the worst: “I don’t know.”

Friends, and strangers reading this, listen to me:

  • Stop being your own worst enemy.
  • Stop being the force that keeps you immobile.
  • Stop being the cause of failure before you start trying.

The reality is, in most cases no one will be there to give you permission to act. To try. To succeed. And to fail. No one will take you by the hand and say, “Now it’s time. You’re ready.” No one will be so sure to say, “Don’t worry, you won’t fail.” No one will lay their hand on yours as you click that submit button, as you fill out that form, as you sign up for that chance, as you raise your hand.

You can be surrounded by a loving family and supportive friends, but ultimately that conviction has to come from within you. So give it a chance. No, not just that. PUSH IT.

And leap. And try. And do.

And yes, you might fail. And yes, you might sometimes look stupid. Or unprepared. Or lost. Or audacious. Or wrong. Or arrogant. Or ballsy. But you also might not. You might surprise yourself. And slowly those lost and unprepared times might become the minority rather than the majority, and soon you are looking at the Past You from a vantage point you didn’t know existed before you decided to try.

I think I’ve had this feeling inside of me for a long time, but it wasn’t until I read this, 2.5 years ago, that it became a solid concept to me:

“Because, at the end of the day, they can still say no. The powers that be can tell me I’m not a good fit — but I shouldn’t be doing that job myself. Who knows if I would have been picked, but I made sure that I wasn’t. I rejected myself [let me repeat that: I rejected myself]. I don’t want to do that anymore.”
Tea & Cookies, Throwing Your Hat into the Ring

A week later, I sent in my job application to Automattic. I threw my hat into the ring.

So, it’s a simple message, but a difficult one for many people to really embrace.

Step out of your own way. Once you do that, give yourself a push forward, too.

I’m not going to let just my words convince you – here are the best of the best articles I’ve found in the last year or so that reinforce this concept. If you have an article or post to add to this roundup, leave it in the comments!
Here’s how you can stop sabotaging your own success:

You’ll need to use confidence as a tool in risk-taking:

“What it taught me was you have to be very confident, even though you’re so self-critical inside about what it is you may or may not know. And that, to me, leads to taking risks.”
Virginia M. Rometty, HBR’s Why Women Leaders Need Self-Confidence

You’ll have to do things you haven’t done before:

“You can’t let what you know limit what you can imagine. As you try to do something special, exciting, important in your work, as you work hard to devise creative solutions to stubborn problems, don’t just look to other organizations in your field (or to your past successes) for ideas and practices. Look to great organizations in all sorts of unrelated fields to see what works for them — and how you can apply their ideas to your problems. Who are the most unlikely organizations from which you learn? Do you have new ideas about where to look for new ideas?”
Bill Taylor, HBR’s Don’t Let What You Know Limit What You Imagine

You’ll need to push yourself to continue when that something is uncomfortable and even painful:

“But here is an E that we need to always be working towards getting more comfortable with…Getting comfortable with being uncomfortable. Pain. That little red alert gauge starts to light up when we feel that pain, that burning, the lactic acid shuffle. Our mind starts telling us to back off and cool it, but here is where we need to play chicken with that blasted little needle and E alert sign.”
The Arty Runner Chick – Redlining and the All-Important E

You’ll need to stop worrying about what your success looks like to others:

“Success and likability are positively correlated in men, and negatively correlated in women. Women must worry about how ambition ‘looks’ because appearing ambitious negatively impacts their success.
The Next Women, Busting the Myth That Women Are Less Ambitious Than Men

You’ll have to do as other successful people do, until you’re successful yourself:

“When we expect to do something perfectly right out of the gate, we make tons of mistakes…Intelligence is malleable, and it grows with experience….Anyone can get more willpower – it’s developed over time like a muscle.”
Harvard Biz IdeaCast 273: What Successful People Do Differently

You’ll have to adopt a growth mindset basic talents & abilities can be developed over time through mentorships & experience (and you need to start today!):

“These are the people who go for it….they’re not worried about how smart they are, how they’ll look, what a mistake will mean. They challenge themselves, and grow from that…Challenges are exciting rather than threatening. Instead of thinking ‘I’m going to reveal my weaknesses’ you think ‘here’s a chance to grow’…You’re focused on the process instead of just the outcome.”
Carol Dweck, Mindset: The New Psychology of Success.

You’ll have to accept that self-promotion doesn’t have to be annoying or “dirty”, but it can be useful and relevant when done right:

“Perhaps the challenge isn’t learning to become more comfortable with being self-promotional, but rather learning to play within the range of what your community considers acceptable (defined by your own bullshit meter). That means if you tend to feel uncomfortable promoting your work, endeavor to squeeze in a bit of personal PR thoughtfully and remember: There are some real freaking crazies out there who actually want to read your stuff, see the pics of your trip to LegoLand, take your teleclass. And who are YOU to not deliver? You see? It’s really not about you.”
Jory Des Jardins, Do Nice Girls Self-Promote?

You’ll have to start defining yourself by what you want to become, not only what you’ve accomplished so far:

“Which leads to a question about how do we define ourselves? Is it just what we’ve done? You’ve already heard me say that, we are always 2: Who we’ve been, and who we aspire to be. Each of us is bound by our past, our accomplishments, and our failings. But I believe we are ALSO our aspirations and dreams. If each of us has a self-definition that allows us to appreciate the creative act of the moment…then we will stop denying energy to it. We will be okay with the trying and experimenting. Look around at any innovative company, and notice….they are okay failing because their self-definition includes the idea that they will ultimately figure it out.”
Nilofer Merchant, 2 Ways to Skirt Self-Handicapping

You’ll need to raise your hand to be called upon, and expose yourself to judgment, or risk doing nothing:

“In these circumstances, people who don’t raise their hands don’t get called on, and people who raise their hands timidly get called on less. Some of this is because assertive people get noticed more easily, but some of it is because raising your hand is itself a high-cost signal that you are willing to risk public failure in order to try something…. To put yourself forward as someone good enough to do interesting things is, by definition, to expose yourself to all kinds of negative judgments, and as far as I can tell, the fact that other people get to decide what they think of your behavior leaves only two strategies for not suffering from those judgments: not doing anything, or not caring about the reaction.”
Clay Shirky, A Rant about Women

You’ll have to start taking action to get results:

“Own It. It’s time. If we don’t have the confidence to take a shot at what we want in the business world, there’s a 100% chance we will fail. Basic math. Lack of confidence plus lack of action equals zero opportunity for success. It’s a game of confidence, action and results.”
Amy Jo Martin, Let’s get out of our own way & start owning it

You’ll need to learn how to negotiate:

“I work for a large multinational tech company, I regularly hire woman for 65% to 75% of what males make. I am sick of it, here is why it happens, and how you can avoid it.
TwoXChromosomes on Reddit

You’ll need to keep yourself in check:

“And if you don’t check yourself before you wreck yourself, you’ll damage your own self-esteem, stand in the way of your own goals, and maybe even sabotage precious relationships.”
Fearful Adventurer

You’ll need to hold yourself accountable:

“I am so done with letting my own insecurities, self-doubts, and regrets hold me back.”
Sarah J. Bray

You’ll need to act:

“If you have a lightening bolt idea, just DO it. Execute the bare minimum to get your idea out into the world.”
@maggie #altsummit via @nicoleisbetter

You’ll have to take a seat at the table:

“Believe in yourself, negotiate for yourself, believe in your own success.”
Sheryl Sandberg, Why we have too few women leaders : some insights on how women evaluate themselves

It will all start with YOU.

(And watch Sheryl’s video at TED, too):

This blog was originally posted at When I Have Time.

Photo credit: Peter Kaminski on Flickr.
About the guest blogger: Sara Rosso is the VIP Global Services Manager for Automattic. She is a writer, photographer, and business & digital strategist living in Milan, Italy. She’s worked in technology since 1996 for companies such as HP and Ogilvy. She has an MBA in Managing Innovation & Technology from Santa Clara University in California, and a bachelors in Managing Information Systems from Texas A&M University. Follow her on Twitter at @rosso.