Making a mess of asking

“You might as well just ask” / “Just go for it?” / “What’s the worst they could say? ‘No’? That’s not so bad!”

Worm's personal purposeI have read and given this advice a hundred times. It’s good advice. Mostly.

We don’t even think to ask for what we want, because a lot of times, we feel like if we ask, we’ll get turned down. There’s something else we need to do first: There’s some credential we need to get; we need to shoot some photos first; we have to put together the pitch or the catalog first.

There’s a window of opportunity and we aren’t prepared to go through it just yet.

So the advice is to just go through it anyways — barge in there with who you are, let them tell you “no,” and maybe let them tell you “yes.”

Is this advice any good? Should you prepare? Or should you just wing it?

When we first started the business, I would reach out to press and retail shops hoping to get coverage or make sales. I look back on these awkward messages now and I cringe: Did I really send those crappy photos? Did I really spend so much time talking about the our business, and so little time talking about the products? Couldn’t I have spent a little more time crafting our offering so we didn’t seem like such amateurs?

These bridges are probably behind me. I can’t reach out to them again even though our pitch is much more refined and optimal.

I went for it anyways, and because of that, I have a whole bunch of cringe-worthy pitches to companies who were, frankly, out of our league at that time in our business.

Having done that – the thing most of us are not willing to do – I lived, and I’m here to share the results with you.

90% of those pitches went unanswered.
Of the 10% who got back to us, probably 8% said something nice like “No, thanks. We’re focusing on [xyz other thing] right now.”
Of the 2% who didn’t politely decline, we’ve had mixed results:

  1. One was our first wholesale account, Marion & Rose’s Workshop, in Oakland, California
  2. One was Cowboys & Indians Magazine, who featured us and opened a whole new channel for us (the cowboy crowd)
  3. One was UNFI, the largest natural food distributor in the US, who started carrying us

Not one said “Get your fucking act together, you amateurs!”

That’s our worst fear, right? Well, that or the silent dismissal of people who think we aren’t even worth responding to… which arguably, that 90% could be interpreted as (it sure feels that way) — though it’s important to remember that it actually isn’t that way, we just imagine it is.

And of those 90% of people who didn’t respond, we are free to follow up again once we’ve got ourselves differently positioned. In fact, that different positioning gives us a great excuse to follow up: “Howdy! I thought I’d reach out since we have this new product line / set of photos / because I saw you recently posted about [subject that is related] and found your post very insightful.” Be nice, but be persistent.

I can tell you from experience, it is non-fatal to act before you’re ready, and you might even get some great contacts and results out of it!

My Secret to Continued Productivity? The Checklist of DOOM! (by popular demand)

Some things are quick, one-time things: you fill an order or you respond to a customer query.

But some things can’t be achieved in a few days or weeks: organizing all your finances for taxes, working with press, and writing a book.

These require tireless persistence, focus, and dedication. I have none of these things. Not. A. Single. One.

When I was on Adderall (prescribed for my ADD, not recreational), my lack of focus wasn’t so bad. But that made me irritable, and in the interest of keeping peace in the household, I had to give up the Adderall.

Enter: THE CHECKLIST OF DOOM

I’ve developed a weirdly non-technical way of managing these tasks over long periods of time, but it works, so now I am on something like version 8 of The Checklist of Doom. Every time, I refine it a little to account for my changing priorities and lessons I learned from the previous checklist.

Sometimes the checklist includes personal things, sometimes it includes only business, sometimes it includes fitness. It’s so personal both to the individual, and to the individual in that time. I have created a worksheet to create your own, since I love how fancy that is.

Here’s the philosophy behind the The Checklist of Doom:

We all have long to-do lists that we carry around with us, either physically or digitally. These are good for managing short-term tasks that can be achieved and crossed off.

The truly Great Things, however, require months of dedication.

Like eating an apple, if you try to shove the whole thing in your mouth at once, you’ll choke. The only way to eat the apple is bite by bite.

You have stuff to do!

Accounting is the perfect example of this. How many of you scramble around for the week before taxes, frantically itemizing everything before you can send it to your accountant? (Probably more applicable to small business owners than W-2 employees.)

Not me. I exported my Profit and Loss (P&L) and sent it to my accountant in about 5 minutes. BOOM.

I also manage my press and retail contacts as items on the checklist, because there is no immediate reward for writing press (it takes literally weeks of follow-ups to even get a response, if you get one at all). Without the checklist, this activity feels endless and futile.

But they aren’t endless and futile. Press seems to be a numbers game, and to get one hit, you have to send about a hundred queries. But you still have to send that hundred queries. The checklist keeps you on task even when you feel most adrift.

You have to do some stuff more often than other stuff.

Depending on your priorities, you might have to update Facebook and Twitter several times per week, whereas you only have to send out your newsletter every two weeks.

The checklist is cool with that.

I’ve created a couple worksheets to help you create your own Checklist of Doom. Sign up for my newsletter to get them:*

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* Look, I know people use handouts like this as a lure to sign up for their mailing list, and this is absolutely no different. However, you don’t really have to download the worksheets to get the benefit, and the newsletter is really great, so… please sign up.

For complete instructions on how to create your Checklist of Doom, I created an instructional video: