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Let’s assume you have the idea (and the skills!) for a business you’d love to run full-time. I bet I can guess what the biggest thing in your way is.


I know because I’ve been there. It was the biggest barrier for me, too! Today I’m going to share exactly where my first clients came from, and principles you can use for finding your own clients, too.

This is super important because we’ve all had an idea that we imagine could make us a lot happier (or at least a lot more successful).

We know where we are now—let’s call it our current job— and we can imagine that awesome future in which we do what we want to do.

But if this rings true with you, you’re already thinking, “Sure, Jeffrey. But I can’t just flip a switch and go from my current situation to an ideal one.”


In fact, that awesome future is going to take a lot of work . . . probably more work than your current job demands. And it will probably pay less than your current job from the get-go, too.


Maybe that original diagram is missing something . . .


Ahh, that’s more like it.

And let’s make even more realistic, because the “getting there” part is often scarily below the “what I need to get by” line, right?


Yeeesh. That’s a gap.

The trick is to bring that “getting there” income up to a point at which you can still get by before you quit your current job.

Once you can make this scenario true, that awesome future becomes a lot more attainable.


I made that happen by lining up clients on the side.

And here’s where I found those clients, and how you can start finding clients, too.

1. Turn previous work relationships into clients

Remember Career Chicken? Turns out you can make really, really good impressions on people when you’re working your butt off trying to get better at working your butt off.

My first paying client for what is now Overthink Group was actually a friend I made at that old workplace. He was several rungs up from me in a different area of the company, but he knew what I was good at. He left that company and started working somewhere else as a marketing director. Because I already had a good professional relationship with him, it wasn’t hard to pitch him on hiring me.

You can do this, too. Think of the people you’ve worked with who have since become decision-makers at other companies. Is there any way you can give them a hand? Reach out to them and see if they’re interested in hiring you for some freelance work.

This can be as simple as sending someone an email to the tune of:

“Hey, old friend! I’ve started a new business on the side doing [the stuff I’m best at]—is there anyone you know of who might be interested in my services? (I’d love to work with you again, by the way!)” That deal began as a $1000 project, but became a much larger client over the next few months.

2. Turn your hobbies into clients

The second client to pay me had actually been following the blog I’d been keeping. I was running a Bible-study blog, and he was the president of a Bible college.

He reached out to me and asked if I’d be willing to do for him what I’d done for myself—and I sure was! That became a monthly retainer of $1,600.

Of course, this works when you have an established reputation with a number of people. If you don’t have a blog, email list, Instagram following, etc., then you probably won’t have a following to draw from in this way.

3. Make a hard sell

I knew I could make it as a consultant because VIPs at my employer’s company wanted to hear my thoughts on things. I assumed that these weren’t the only C-levels and VPs who could benefit from my knowledge . . . there must be others at different organizations who had similar problems.

So, I reached out to a manager at another company to see if he’d hire us.

He knew I could help him. And I knew I could help him. So I pitched him on hiring me, Laura, and our first teammate as an agency.

And it happened: we landed a $5,000 monthly retainer, which has since grown into a $12,000 monthly retainer.

4. Bring your employer aboard

Working for yourself doesn’t have to mean saying goodbye to your employer. I really love the team I used to work with full time, and didn’t want to leave them entirely. So, I pitched them on becoming a client. I’m glad they said yes. =)

Note: this isn’t always something you’ll be able to finagle. Some employers won’t be too thrilled about you “moving on,” and so this may be a closed door to you. But it doesn’t hurt to ask.

Important: I couldn’t do all this myself

Full disclosure: I launched this agency with my wife Laura as a business partner, who had recently quit her full-time job. She was building the infrastructure for our business while I was winning clients and working full-time. There’s no way we would have grown so aggressively if I’d been doing this myself.

And that wasn’t all the help I had. Jayson D. Bradley, an old coworker of ours, joined the team full-time before I was full-time on Overthink Group. Why? His skills were vital to a few of our early contracts (and have continued to be vital). It was a smarter move for me to hire someone to help us with one contract so I could win a few more.

In the end, I made the jump!

By October 2015, Overthink Group had made more money in three months than I had in the previous year. It was clear that this was where I should be focusing my time and energy. We had more prospective clients lined up, and we had faith that there were more great clients out there.

So I took the plunge and joined Laura and Jayson: Overthink became my sole source of income.   

The next few months involved a few more clients agreeing to work with us—and within six months, we had more than $300,000 in billings lined up.

Now, what does this mean for you?

I believe that there are several people out there who can do what I did. I think there are smart, ambitious, genuine people who don’t belong on anyone’s payroll. And if you’re that kind of person, I want to help you gain the perspective and strategic thinking skills you need to do what I did: get an awesome job working for yourself.

I don’t think everyone falls into this category, though. Some people are better set up to win at self-employment than others.

I’ll share more on that in tomorrow’s email. =)

But for now, I’m curious: does the illustration above resonate with you? Have you figured out your minimum-viable income? Or maybe you’re in the “getting there” zone. Would you leave me a comment to tell me about it?

This is the first of a four-part series of posts on how I made $300,000 in six months by launching Overthink Group. Don’t miss parts onetwo, three, and four!