Articles And Guides On Freelancing

Conferences are a hell of a lot of fun. When done right, they’re also very rewarding — both for the organizer and the attendees. I get to meet many of my customers in person, which to be honest is a bit of an ego boost. And the people who go usually get much more than they put into it… new connections, new friendships, and new ideas.

The problem is that from a business + focus perspective, DYFConf hasn’t been the best “product” for my company.

Every year we’ve either lost money or broken even.

Every year we’ve just barely had enough attendees (I was almost on the hook for paying for about a dozen empty hotel rooms last year because of how hotel group discount blocks work.)

Every year we’ve struggled to even secure 2 or 3 sponsors to help offset costs.

And every year it’s taken dozens of hours of time to promote, get speakers, deal with the venues, etc.

So from a purely business perspective — there are other things we should be doing. But until now, I’ve justified it. “It’s good for the brand. It’s good for attendees.”

“Choosing a niche,” or coming up with strong business positioning, is one of the most difficult exercises for many of the freelancers I’ve worked with over the years.

I think they point to a big disconnect between what niching actually is and what niching is thought to be.

What does it mean to niche?

Every transaction requires an application.

If I’m going to buy a new computer, justifying the purchase requires me to think about how I’ll use the laptop to better my business or my life. Why I end up buying a laptop is different than why you might buy that same laptop.

Likewise, hiring a freelancer (for the sake of argument, let’s say a freelance web designer) requires the business owner to rationalize how they’ll use the web designer to achieve the end they have in mind.

Consider for a moment the lifecycle that goes into hiring somebody like you:

1. A business becomes aware of a problem that they have
2. They realize that this problem can be solved
3. They then determine someone like you can solve the problem
4. They seek out people like you

That flow carries a lot of risk.

Companies that could benefit from working with you easily fall out of that funnel. Most businesses never realize that they even have a problem, or that it can be solved. And the ones who do realize that they have a solvable problem don’t know that finding someone like you is the best way to solve it.

For every one business that makes it to the end of that funnel, dozens or hundreds self-select out of it.

So to plant your flag and say “I’m a web designer, hire me!” you’re excluding a large part of the available market from ever finding you because they…

• Don’t know they have a problem that you can help them solve
• If they are aware of the problem, don’t know it can be solved
• Don’t know that a provider like you can solve their problem

This article is somewhat specific to the needs of freelancers who live in the United States, but I’ve tried to make it useful no matter your country.

I remember when taxes used to be relatively easy.

I’d get my paycheck, my employer would withhold estimated tax payments, and at the end of the year I’d file a relatively simple tax return and get a refund for any withholding overpayments I made a bit later.

Easy, right?

And then I started my own business.

…And the IRS went from being a faceless organization that mailed me checks every year to an archnemesis, who I felt was always getting in the way of me, my clients, and even my ability to create jobs.

I dug myself into a hole more times than I’d care to admit, especially as I grew my agency and brought on employees and significant overhead. Early on, I thought of my taxes in a very laissez-faire way: “yeah, I’ll owe some taxes probably, but hopefully I’ll have the money to pay them. And if not, I’ll get a payment plan worked out. What’s the worst that can happen?”

To be honest, it wasn’t doom and gloom.

I did end up taking up the IRS on a payment plan, and it was easy to do. (If you owe less than $50,000, you can usually do this without even needing to talk to an agency. If you’re like me and don’t like needing to tell someone that you screwed up your taxes, that’s a very welcome featured.)

But don’t be like me and end up mucking around with IRS payment plans.

If you take one thing away from anything I do here at Double Your Freelancing, it’s this: Learn as much as you can from those who’ve already forged the trail.

So today I’d like to introduce you to Luke Frye of Timber, an accounting firm that specializes in working with freelancers. He’s helped me prepare this article (since I’m woefully ill-equipped to talk authoritatively about taxes or legal things), and his firm has also produced a really good email course that goes deeper than what we’re able to cover in this article—I’ll link you to that at the end of this article.