How Do You Know When You're Ready to Move to the Next Level?

This guest post was contributed by friend and SOB, Sheila Scarborough. Her advice here is flawless and based in deep expertise. –ME “Liz” Strauss

Moving To The Next Level

by Sheila Scarborough

Most entrepreneurial online “digital creatives” find that their business moves through a progression.

At first, many writers, Web designers or other content providers often take most any job as long as it pays. In the quest to amass a decent portfolio or group of clips, it’s easy to succumb to the siren offers of “revenue sharing” or “exposure” or “future growth,” rather than demanding a higher per-word or per-project rate.

Blog for $50/month and post 5-7 times a week? Sure!

Heck, blog for nothing and hope for some ad revenue? Sure!

Anything to get a toe-hold as a freelancer.

There comes a time, however, when the digital entrepreneur is ready to truly make a living in his or her area of expertise, maybe even to be able to drop the side job that actually pays most of the bills.

How do you know when you’re getting ready to move to the next level?

I’ve asked myself that question a lot lately, as I approach two years as an active freelancer (a writer and blogger, in my case.) Here are some benchmarks that I’ve stumbled across at this juncture; you may find some similarities to your own situation, or as a newbie you can look forward to someday grappling with these turning points:

1) You can’t work by the seat of your pants anymore.

Perhaps you have more than one blogging commitment, plus offline work and some clients and consulting. Life starts to implode, you meet all of your deadlines but just barely, you gain twenty pounds, the house is a wreck and upon awakening you think, “Oh, no, I have no idea what I’m blogging about today, plus there’s a client meeting that I’m not ready for this afternoon and an article deadline by close of business.”

It’s time for a schedule, because it’s time to admit that this is your job and you’ve gotta get organized. Big wall calendar, some online software, a PDA, an old-school Filofax, whatever — you’re at the stage when you must get a grip on the madness. It’s time to hire a CPA for taxes, it’s time to buy Quickbooks or other bookkeeping software to track invoices, it’s time to buff up that blog/Web site, it’s time to….move into the bigger leagues.

2) You are ready to build a specific or at least semi-defined expertise.

At first, entrepreneurs will do most anything to make a buck, even if it isn’t what they like or isn’t what they’re very good at. For a PayPal transfer or an actual check, I’d write about most any topic when I first started out, for any publication that was halfway legitimate.

At some point, however, you know which subjects really make your heart sing, which ones call forth your best work, and it’s time to begin to focus and hone your expertise and creative efforts.

For writers, this is the moment to say, “You know, I write mostly about X, Y and Z. Someday I’d like to touch on A and B, but right now, I specialize in X, Y and Z.”

This is different from what you said in the beginning, which was roughly, “I’ll write about anything.”

3) Your time and effort are worth something to you.

At first, many digital creatives are so eager to succeed, they’ll leave no stone unturned to get their business off the ground. They sign up for every e-newsletter and magazine that seems professionally helpful, they have a gazillion RSS feeds, they go to every meeting that seems like a good networking opportunity, and the answer to every problem is to throw more work hours at it.

I personally have reached the point of admitting that I can’t know everything. I can’t read it all, can’t track all the feeds, can’t answer all the emails and memes, and most importantly, I should not feel horribly guilty about it.

To do my best work, I can no longer allow myself to overload my own brain. It’s time to prune the RSS feeds, not follow everyone on Twitter who follows me, unsubscribe from emails that I don’t really read nor care about, all so that I can concentrate on the information flow that is most helpful in my work.

It’s also time to be paid what I’m worth (for a writer, that’s no less than US$0.50/word and preferably US$1.00/word, and roughly $20/post for blogging) and to cast an unfriendly gimlet eye on work that may require a lot of wheel-spinning for a monetary pittance. Some occasional work may be worth lower or even no pay, for a variety of reasons, but my going-in position has shifted to an expectation of decent pay for the work that I do, rather than pleased gratitude that anyone pays me at all.

It’s scary to realize that your baby, your business, is at a turning point, but the good news is that it’s time to make some tough career focus decisions because….you’ve done well and are ready to do even better!

–Sheila Scarborough You’ll find Sheila and her blogs at

Isn’t Shelia amazing? So why not tell her? How will you know when you’re at the next level? Could you be there already?

Work with Liz!!

Sheila Scarborough Is a B.A.D Blogger
Roving Sheila at SXSW 03 -09-07
Roving Sheila at SXSW 03-10-07
Roving Sheila at SXSW 03-11-07 and 03-12-07
Roving Sheila at SXSW Finale


  1. says

    This is good information that I haven’t seen summarized anywhere else. Even though this is not my particular trajectory, I do have clients that are working in this direction.
    I will pass this along. Thanks! :-)

  2. says

    this post speaks to me BIG time, thanks for describing the I will write anything for a resume piece example ( hello – — me !) and for detailing what might be fair to be paid — it’s exciting to imagine getting paid for my writing and I feel blessed that I didn’t sell myself short( or too short anyway ) in the few things I have done so far.

    It’s very nice to meet yet another friend of Liz’s and someone who’s experienced what I am about to embark on and who can share it so effortlessly

    Mother Earth aka Karen Hanrahan

  3. says

    Speaking from personal experience, you’re right on the money. And, I think it’s important to stress that you will come to this same conclusion in different ways as time goes on. You will one day decide that it’s time to shift priorities, and give your time and attention to another area for a while. That’s OK. The point is to not beat yourself up for the things you’re NOT doing, but instead pat yourself on the back for all that you do accomplish. The key is staying focused on your goals…not becoming confused and disorganized by other things. Always remember to take a break from hacking through the forest to climb to the top of the trees and look where you’re going.

    Anita Bruzzese

  4. says

    Great post Sheila and boy can I see myself in what you are writing…the first steps when you just grap out for anything that lets you write anything and everything… to the slow realization that you have to find a way to structure and plan not only what you are going to write about but also how to get paid what it’s worth…the turning point…

    thanks for writing such a thought provoking post…


Leave a Reply

Your email address will not be published. Required fields are marked *