This is what you wanted. This is what it takes.

This is what you wanted. This is what it takes. |

I’ve been thinking a lot lately about the cost of doing business. We’re always talking about the good stories and the triumphs, but I want to share more of those what-the-hell-am-I-doing moments, when shit hit the fan.

Not because I want to bring all of the debbie-downer vibes to the game, but because I think its good to share these stories and know that crap happens to everyone, no matter what stage of business you’re at.

So this time instead of sharing some of my own stories I asked a few of my boss friends to tell me a time when shit went south but they got through it…

David Sherry / Death to the Stock Photo

When we sold our Mystery USB product (a physical disk drive that was full of products for makers and artists) we sold out in the first 24 hours. Now, we messed up in a few ways here we didn't expect.

The first was that we didn't have international shipping, but we emailed everyone in our audience, including those all over the world about the product. They were super disappointed and wanted to buy but we had NO process for getting the item to them. So we were handling some customer service for that. THEN, we were running a super close deadline to Christmas, and realized that we sold more USBs than we had supplies (cards, packages, USBs etc.) for. So I overnight shipped multiple items from Amazon.

We had one of our designers overnight a box from Portland. And then scrambled to get everything out. It took 3 and half days straight of packaging, loading USBs, putting on labels, and praying that everything would get there in time!

Shauna Haider / Nubby Twiglet + We Are Branch

When I started freelancing, I was easily flattered by any potential client who liked my work and had a budget. My enthusiasm got the best of me and I was quick to take on projects without questioning if they were the right fit.

After you’ve had few poorly chosen jobs go bad, you quickly learn that money comes and goes while ethics are everything.

One particular project still stands out: I’d met her a month earlier and immediately liked her so when she asked me to redesign her website, I jumped at the chance…without doing my homework. As we dug in, the red flag appeared: she had almost no content besides minimal text and a handful of images embedded in an ancient flash site. I carried on anyway, doing a round of quick mockups with placeholder content to keep the project moving but she was unhappy with the look of the outcome.

It soon became apparent that she didn’t have the content I needed, no matter how many times I asked (and I couldn’t deliver her dream project without the content). After mutually agreeing to cut ties, I learned my lesson: do your homework BEFORE you start a project because the more informed you are, the more you can help a potential client prepare.

Remember, most clients haven’t worked with a designer before. It’s YOUR job to inform them about expectations, necessary assets and deadlines. Be proactive, be honest and be professional. Things won’t always work out but learn from your mistakes and take the high road — never blame a client for a project’s shortcomings.

Hillary Weiss /

I've had designers who've left me hanging after months of discussion. I've walked into meetings with agencies with toilet paper flecks on my face. I've been fired by a holy grail dream client (years ago), and hired by million-dollar companies with shiny facades that hid complete internal chaos.

There's no escaping the bumps (and why should you? They're teachers in disguise that give you great stories to tell over drinks.) But you do have to be tougher than they are. As they test your stamina, drive, self-worth, and resourcefulness, you'll have to remind yourself: this is what you wanted, and this is what it takes.

Whatever you do, hang in there. You got this. And I promise you, it's always
worth it.

Shaun Singh /

Firstly, fuck everyone who says “Fail fast” or “Embrace failure, it’s great”. Failure is a tragedy and it sucks so bad, in fact I never see myself getting used to it. I still swear at my laptop screen daily and I’m cool with that, it just means I care about what I do.

However, not all failure is created equal. There’s failure and then there’s stupid failure. This is an example of the latter.

When I first launched my online bookkeeping service Change, I fell into that trap of “thinking global from day one” because some VC told me to. This was the worst advice I ever got. I tried to offer a global bookkeeping service by myself. *I cringe just writing that* but in my defence I was high on a deadly concoction of Tim Ferris podcasts and multiple ‘The Lean Startup’ reads,  so I said to the world, “come at me, bro!”.

I launched and people from 14 different time zones started signing-up and booking times with me to chat as I had an open calendar link in my sign-up email. I promised them the world and took their money. My life was fucked. I had meetings at crazy times through the day and night. I was hardly sleeping. I hated my life.

But I thought this was the “Start-up hustle” so I pushed through it... I maintained it for around 3-4 months until I crashed and burned. Hard. The service suffered and most people left. I didn’t blame them.

But I thought I had to be global, right? That’s the cool thing to do in the startup world. No. It was such a wake-up call.

This scared me straight and I went in the opposite direction and re-started SUPER small. I started local. As in my first customer was my next door neighbour and I went from there. It was so much easier than trying to accommodate the world. Why have 20 clients in 20 different cities when you could have 20 clients just down the road? Your income is the same, just MUCH less stress.

Moral of story: Follow the path of least resistance. No need to be a fucking hero. 

So yeah, shit happens to all of us. And even as your business grows, I don't think you can really avoid mistakes or things going wrong... You just get better at learning how to deal with everything.

At the end of the day, you just gotta stay in the game.

p.s. I totally stole the title for this article from Hillary’s piece. Because she’s a word boss. And she said I could.