Cultivating Boldness: How to Be a Bold Freelancer

Credit: photo by shodensan on Flickr
A few months ago, as I was engaged in some much-needed tidying of my desk, I discovered beneath a stack of index cards and tangle of wires a magnetized card with the following quote:
“You gain strength, courage, and confidence by every experience in which you really stop to look fear in the face…Do the thing you think you cannot do.”
– Eleanor Roosevelt
I bought this card many years ago when I was going through a difficult period that had nothing to do with freelancing or writing. Back then, I would wake in the morning and reach for this card, which was waiting for me on my nightstand. For a long time, this quote helped me to get out of bed every day and fight the good fight.
Happily, my life has since moved on to a much smoother phase. Nonetheless, after finding the card on my desk, I propped it next to my computer. As a freelancer, it’s good to have a daily reminder to be bold.
Boldness is vital to a successful freelance career. This path we’ve chosen – the very initiation of which took guts– feeds on determination, confidence, and the occasional death-defying leap of faith. But it’s not just the brassy acts that fuel our career. Freelancing thrives on those small daily acts of daring that aren’t a big deal to anyone except for you. You know what I mean. Picking up the phone and making the call that you dread. Opening the file of a project that seems overwhelming and scary. Taking a good honest look something you’ve labored on for hours (or days) and saying, “You know what? This is crap!” and starting the job from scratch. Deciding to raise your fees.
These acts of bravery, big or small, are the things that propel our careers forward. And that’s why we need to take stock of the areas in which our courage is lagging, every single day. Here are my “BOLD” tips on how you can make sure you’re giving your work its daily dose of boldness.
Brainstorm
Spend an hour writing down all those aspects of your work that you fear, dread, consider yourself weak, or on which you find yourself procrastinating. Dig as deeply as you can. It may help to take a look at your current projects and monthly and annual goals (you do have those written down, don’t you?) to assess the tasks you need to accomplish to finish the projects or meet those goals. Ask yourself which of these tasks require boldness on your part. When you’ve finished brainstorming, make a master list of every individual task that you believe embodies an act of boldness. Put this list on a prominent place in your workspace. You can call it your “Be Bold Goals.”
Obligate Yourself
Commit to doing one bold act a day. When you begin your work day, look at your “Be Bold Goals,” and chose at least one item to accomplish that day. If necessary, promise yourself a little reward as incentive for executing the task (chocolate is always good). Or if you prefer, self-impose a sanction (no chocolate for a week). But chocolate aside, I find that one of the most effective ways of motivating myself is visualizing how I’ll feel once the task is finished. Completing something courageous is as good as any chocolate high. Usually.
Lessen Your Fear
Because bold acts can loom so monstrously large, sometimes you may need to put things into perspective before plunging into boldness. Whatever you’re doing, though important for your business, probably will not have as sweeping an impact on your life it may feel. To shrink your apprehension to a reasonable size, think to yourself: will this act kill you? No. Will it hurt someone you love? No. Will it destroy your entire business, and force you to live on the streets? Probably not. Does it require taking the One True Ring to Mordor and casting it into the fires of Mount Doom? Unlikely.
Sure, deciding to put yourself out there, risking rejection, ridicule, or maybe even money, can be stomach-sinking feeling. But when it comes down to it, all you’re just doing with this act is either pushing your business forward, or gaining valuable experience and knowledge. That’s all. This is true whether your act succeeds or tank.
Do it
Once you’ve committed to a daily act of boldness, pull a Nike and just do it. This is the hardest part. If you employ all the tricks mentioned above and find yourself still hesitating at the brink, try this: pretend you’re someone else. Think about a person you admire, whom you consider to be successful or talented, and whom you believe could more than capable of handling to task you’re about to execute. And then be that person. With enough time and practice, maybe someday you will be.
What techniques do you use to bring boldness to your freelance business?
Credit: photo by shodensan on Flickr



I personally i am not the type to take an hour and make a list – for some reason when i tell myself “ok, from 8-9 you are going to think of goals” i go completely blank. but i do keep a list of goals on a notepad next to my computer that i add to whenever something comes to mind. i have been doing this for years, of course, i never really thought of them as goals but more along the lines of things to learn/try/do. which now that i think about it those notes have really steered/defined my career so far… Great article, first one in a while that really got me to reflect on my career/learning goals
Oh yes! The “obligate yourself” part is something I have to learn: I hate administrative tasks and it takes me a lot of time to decide how and when to deal with them, but as soon as I’ve done them, I feel so happy and free. Thanks for the good tips.
The #1 thing that increased my boldness quotient was committing to finding new clients by cold calling. While it’s true that there are a lot of no’s out there in cold call land, you can also find the most lucrative clients you’ve ever had. And you will absolutely lose your fear of rejection.
Being bold is good advice. some specifics in this regard would be helpful.
So it goes…
-dp
This is one inspiring post and that’s one inspiring quotation. Thanks for sharing, it actually encouraged me a little to keep going at what I’m doing.
“Lessen Your Fear”
I like it. Very master Yoda. Now there’s a great idea for a blog post!
Agreed, often I find when I decide I am going to do [difficult/bold task], the more I hesitate, the more I stress and sweat about it. Often its easier to say “Today I’m going to do this [difficult/bold task]” and then do it right there and then. However, sometimes a little planning is needed
Nice post, thanks.
I think that at first boldness isn’t a characteristic that everybody has. As a beginner, in any field, you have to gain some experience in order to be able to trust yourself, and more importantly your skills.
I believe that in order to maximize your marketing strategies you first have to think that you are the best in your domain. Otherwise it will be very hard to stand up from the crowd.
Barbara,
I just wanted to throw a quick “thank you” out there for allowing me to admit that there are some things about this incredible freelance life that scare the living —- out of me.
It doesn’t mean I’m going to fail, although sometimes it feels that way. But by following your guidelines (which I knew, I swear I did) I can get past these scary obstacles and reach the level of success I dream about.
So, again, thank you.
This article is very inspiring and comes at the right moment for me. Facing a project while I have to learn a new technology to achieve it, all the parts explained in this post are really motivating. Thus I’ll “do it”. Thanks.
Great post. I’m not sure that it needs to take such a formalized approach (one act a day seems a bit much) but I agree that « bold » actions really make us evolve.
It’s important to go beyond our comfort zone. It can be scary but I personally never egretted any of the bold decisions that I have taken. In these situations, when fear kicks in, it’s often a sign that you should move forward.
Hey – thanks for the comments and sharing your own experiences. I’m so glad to know that the piece was helpful!
Great advise! I find that the “thing” you want to do the least, is really the thing that needs to be completed the most. Sometimes, I find myself doing work for work’s sake, just so I don’t have to face the things that really need to be done. Thanks for the inspiration.