I get a lot of notes from people who are starting out doing speaking gigs for money. It’s something I’ve done a fair number of times, and I know how hard it can be to get it right. Not just at first, but really for as long as you choose to do it.

Personally, the speaking stuff is far from difficult for me; but, pretty much everything before and after the gig can be nothing short of a black art.

So, while this thing started as a short email to a friend asking for advice—what the heck. In the interest of saving myself some future typing—and maybe potentially helping people learn what I wish I’d known starting out—here’s one fella’s incredibly opinionated guide to getting a smarter start in speaking for dough.

For a variety of reasons, I don’t do nearly as many talks as I used to, but I’m happy and honored to share the big stuff I’ve learned about the business piece—especially how to recognize and avoid the red flags that I really wish I’d learned to notice years ago.

Thus. Five key points I always keep in mind when considering a potential speaking gig:

1. Know your value.

Above all, understand and 100% accept the unique value of your time and your presence.

Because, “a talk” may be what goes on the invoice, but it’s having you in particular there that should (IMHO) be the primary—maybe singular—selling point AND buying point.

Anyone can do “a talk,” but consider what is unique about your own schtick that (literally) cannot be obtained from anyone else being there instead of you. THAT is what you sell; regard the “content” as an important secondary matter, but never forget that only YOU can do a Your Name Here appearance. Full stop. Thus…

2. Know your needs.

Every speaker, like every human, has their own meter for the trade-offs and challenges of client work (more on this in Point 4).

Learn your realistic needs quickly and always know ahead of time what you’re fine doing and not fine doing and under what conditions either or any of those things are being presented to you.

This is crazy-complicated calculus to be sure, and it will vary hugely by situation, but it’s an admittedly fuzzy equation that’s worth calculating and re-calculating and re-re-re-calculating as you do more gigs and learn what does and doesn’t work for you (and for your clients, for that matter).

Viz.: What’s important to you and what couldn’t you care less about?

The type/size of audience?

The coolness of the host?

The prestigiousness or bounce of the appearance?

Scoring a seat in first class?

Enjoying fresh flowers and free HBO in your room?

Receiving your full fee up-front?

Never traveling beyond 500 miles of your home airport?

Figure these out fast as you can, evolve as needed, and you’ll never have to waffle with a new client. Because you must not waffle. Waffling is death.

Waffling is a long, slow, painful, waffly death.

3. Know your price.

This part sucks and is nearly impossible to get any good at for a year or five, but it’s something you simply must tackle with increasingly less fear and hesitation.

To get the ball rolling from step zero? Based on those preceding two very important foundational points, I’d recommend starting out with a price ceiling and a price floor.

This is a REALLY inexact and horribly artful thing to do, because there are just SO many variables to work out in each gig. Not least of which is your own lack of experience with learning what the market, writ large, thinks you’re actually worth.

Still. The simplest way to start is by coming up with two fuzzy but realistic numbers:

“Yes! I’ll appear pretty much anywhere anytime for any audience for THIS much cash”; and “Are you fucking kidding me?"

Again, inexact and fuzzy. And, yes, these can and should evolve with experience. And, yes, honestly, only you can decide what these bookends are. But, yes, you do want to consider Points 1 and 2 all along the way.

Try starting with what you make before lunch as a floor and what you make each month as a ceiling. Yes. Big spread. Maybe you can do better. But, it’s a start.

Price Sidebar 1: Dealing with, "Mmmmmm…geeeee…I dunno…”

Unfortunately, almost every client will say they’re not sure what the budget is or “it just depends” or “we’re just getting an idea what you charge.” Watch out for these red flags and the potentially dangerous people who wave them at you.

In the best of cases, “we don’t know the budget” people have simply not done their own planning or due diligence, and they should be regarded with extraordinary care and suspicion. Projects have budgets or they aren’t projects.

In the even more unfortunate and, sadly, more common cases, the people who say these things do so because they are—to use an ugly word—cheap. Just as often, and maybe just as bad, they see themselves as doing you a big favor and a total honor to even ask you to appear. Yay, you.

If you are not careful to suss out this situation in your first (or maybe second) contact with them? Trust me. You will die. Because these shitheels are merely waiting for you to be cheap with them. And shitheels are famously patient.

Try this. At least in your head, ask them if they’d fly to your house for the same terms and money and still consider it an honor. Ask them whether the honor of having their job means working for cheap. Or, as is so often the case, free.

Yeah. I thought so.

Price Sidebar 2: Find the Ballpark

Good tip here? If you get into this we-don’t-know-the-budget situation, ask the world’s simplest question:

“What is your orders-of-magnitude budget for my fee?”

1 dollar? 10 dollars? 1,000 dollars? Ten-million dollars?

If they can’t answer this immediately, walk away. They are either insane or dim, and working with the insane and dim brings one little value and much heartache.

Finally, just for fun, if they repeatedly insist that they have no idea what their budget is, give them your “ceiling price.” Plus maybe 20%. See how they react.

I can pretty much promise they will react (in order) with

silence, then, shock, and then, a surprisingly indignant (and very insulting) announcement that you charge too much.

This is how it goes.

SO, at this point, if you really want the gig or just don’t have anything better to do with your time, ask them, “Okay, then. How much did you think this would cost?” or, “Well, what were you hoping to pay?”

And, when, with heretofore unseen confidence and certainty, they sniff something like “$500 plus a bus ticket,” savor the moment.

Because you just learned that, surprise of surprises, they actually DID have a budget, but now you’ve wasted half an hour talking to them, and their credibility is—lucky for you—completely blown.

Things cost money. People either pay for them, or they don’t.

We are gentlemen, and we can disagree on value, but it’s unseemly to tell another gentleman what he’s worth. Learn this fast fast fast.

Price Sidebar 3: Your Terms Matter

Listen: NO ONE is a client until they’ve paid you. Something. Anything.

NEVER take “Net 90” unless you can really afford it or have brain damage.

If you can live with it, demand full payment on or before the day of the gig.

Me? I’m super-fancy. It’s gotta be fifty/fifty. Half the total fee today books the date, and the balance is due in my moist right hand before the gig day.

Yes. I can highly recommend learning from the great Hyman Roth:

I’m going in to take a nap. When I wake, if the money’s on the table, I’ll know I have a partner. If it isn’t, I’ll know I don’t.

It’s simply not a gig until some money is in your hands. McDonald’s doesn’t dole out Happy Meals in return for seemingly earnest IOUs or the promise of magical forms being placed ““in the pipeline.”” And, neither should you. So, don’t.

4. Know your safe word.

I’ve learned that this racket can be really surprisingly time-consuming—just even to vet the seriousness of a given client.

Again, in my case, that’s made me really picky about quickly determining how serious and funded the project is. If it’s gonna take five calls and 30 emails to either deal with administrative BS or (ick) “demonstrate your value,” immediately walk away.

Again, again. Once you deal with anyone in the process who either explicitly or tacitly expects you to defend your price and terms, you’ve lost forever. Now, you’re Willy Loman.

As soon as you feel that lookie-lou, garage-sale-shopper BS or see behavior contravening Points 1-3, just walk away. It’s simply not worth your time to become someone you don’t want to be for bad money.

Thing is: In my experience, the best gigs (and the repeat gigs) come from people who can immediately commit to at least 75% of your rack rate on the first call, feel like they’re getting a good deal (see also point 1), and then bend over backwards to make it easy on both of you.

Fiddling around with anything else is a total grab bag and I’d suggest being circumspect about plunging your hand into it. Unless the gig means a whole LOT to you (see Point 2).

But, then, can you even afford to treat it that way for what they’re willing or able to pay? Be honest.

See: it means everything to me to give a client 100%, and I simply can’t afford to do that if I have to play some ungodly and interminable combination of “Mommy” and Accounts Receivable. It’s excruciating. Avoid it.

Get ruthlessly fast at recognizing unpromising leads, and proceed accordingly. ALL that time you spend on wondering and hoping and cajoling and dealing yourself down is WAY better spent finding, delighting, and retaining WAY better clients.

Never be afraid to say, “thanks for your time,” and walk away—not as a bargaining chip, but as a source of sanity and professional growth.

It is SO not worth the time and effort to deliberately fund your own clusterfuck. Clusterfucks must never be funded.

5. No. Really really know your value.

You’ll be amazed to learn how many people who tell you they want “just a 20-minute talk,” honestly (really, no, really) see this as just a 20-minute time investment on your part. It never stops astonishing me. Never.

But, for me? Once you account for engagement, prep time, travel, admin time, unforeseen time and scope changes etc., any out-of-town gig takes at least three days of my time.

This immutable fact took me five painful years to learn, and I have the scars and holes in my wall to show for it. Because, yes, I used to idiotically cop to the “it’s just a 20-minute talk” then charge like “it’s just a 20-minute talk"—but, then, still treat the gig with all the care and professionalism of fulfilling a contract with fucking Boeing. Madness.

It is NEVER "just a 20-minute talk,” and you’re high to even consider that it might be. In addition to the value and needs you’ve theoretically accepted above, consider the upcoming n hours and days of your life where you won’t get to do other things—including, as I say, landing better and more profitable gigs with cooler people.

So. Trace back through all of the preceding four points and where do you land?

I know why I’m good, I know what I need, I know what it’s worth, and I know what it’s never worth. Because I am an adult professional with a life.

So, anyway. Yeah. This ran long.

Take the gigs that sound fun and give you a chance to grow as a speaker and expose you to awesome people and maybe even make you some dough. But, really, I implore you, never lose sight of these points.

On a personal note? Every time I finally get home from a grinding, shit-paying, soul-bruising gig during which very little value was exchanged between anyone and which I KNEW I shouldn’t have taken in the first place, the same thing happens; I end up back where I started.

I kick myself for missing three mornings with my wife and daughter that I’ll never get back, and I finally turn the blame right where it belongs: to the idiot in the mirror who forgot who he is and what matters.

Then, I go back to Point 1, and I work my way through until I can identify all the places I went wrong. And, then I try not to do it again. And, I make myself remember it can be as fun, profitable, and gratifying as I demand it to be.

Good luck, and speak awesomely, my friends.

EDIT 2012-09-26_15-41-47: Copyedited and cleaned-up for clarity and enhanced betterification.