Q: I’m new to freelancing, although I have a few years experience in design already. How soon should I start approaching the top, highest paying clients? 

I’m concerned that I’m not in their league yet. They may see me as a hopeless newbie, which would ruin my chances down the road. How do you know when to pursue the big guys?


Easy. Pursue them from day one.

Even if you think you suck, even if you think you’re not ready.

If you can identify the A-listers in your field, start approaching them right away. We’re talking about the high-paying ones, the heavy users, the clients for whom your type of work really matters, the most demanding buyers.

If you know who they are, chase them. The top publications, the fast-rising agencies, the elite tech firms, the big names. The ones you are too scared to think about right now.

I know, I know. The usual advice is to start smaller, with the C- an D-listers. Gain some experience, build a portfolio, build your confidence. Work up slowly. Be patient.

I did that. And I was wrong. Wasted a lot of energy and time, mostly because I was just plain chicken.

For one, working with smaller, less-desirable clients doesn’t teach you much about working with the top guys. The top clients are different. What you want is practice talking to them, trying to get work from them, hearing how they think, what they want.

Yes, the high-flyers are hard to impress. They will often ignore you. Or flat-out tell you no. (But, in truth, so will some of the less desirable, small-paying, pain-in-the-ass clients.)  If you’re going to hear a ‘no’, might as well hear it from someone who really counts.

So keep at it. You’ll get better the more you try. You learn to catch the attention of lush clients by trying to catch their attention. Querying Bumptown News won’t teach you how to query Harper’s.

And no, going in too early will not get you branded forever as a no-talent hack. (I had this vision of my mug shot pinned to every Creative Director’s office wall:  “If this moron calls, don’t answer.” As if I were that important.)

Fact is, you are off the radar six minutes after they delete your email. Which is your saving grace.

You can go back fresh in a couple of weeks with a little different approach, maybe a new idea, an interesting portfolio piece. A brand new day.

If they do happen to remember you, that’s good. It means you are in some small way ‘rememberable’.  Which no easy thing.  Plus, they may see you as persistent, as interested. You’re getting better, smarter.

If you get lucky and land an assignment from a biggie, it will raise your game in a hurry. Way faster than doing  low-budget grunt work for client who doesn’t get it.

Start with the A-List.  Take some B- and C-list work if you have to. But only when the A’s say no.

Start high. Work from there.