Thoughts on Becoming an Opportunity Hound & Going After Dream Clients

If you bring big, bold ideas to your clients, you will make a lot more money as a freelancer or consultant. If you wait for your clients to bring ideas to you, you will make a lot less money.

Have you considered emailing that creator, company, or brand you admire and courting your dream clients instead of waiting for them to find you?

In this post, I’ll tell you a story to illustrate, and then I’ll share practical ways for you to become an Opportunity Hound.

Opportunity Alert: “She’s stepping out of day-to-day operations.”

One of my long-time clients is the CEO of an e-commerce company. The CEO wanted someone other than his wife to pass ideas by, and I served as both an advisor and thought partner. He had paid me $1,750 per month for two strategy sessions. Our sessions roamed far and wide: branding, marketing, operations, hiring, product development, you name it.

That changed one day when my client mentioned that his wife would be stepping out of the day-to-day operations of the company after she gave birth to their third child. She had played a role in content strategy, Instagram, customer support, analytics, and reporting, so I couldn’t help but wonder who would be taking her place.

“Who’s going to take over her responsibilities?” I asked.

“Good question,” my client said. “I need to put more thought into that.”

This brief exchange might have passed across my awareness like a cloud across the sky—noticed for a moment and as quickly forgotten—but I’d been training myself to see shapes in the cloud, in this case a dollar sign. Soon after, I fired off an email with the subject line “idea”:

Stuart replied three days later, and my casual proposal, “some sort of fractional CMO role,” elicited two magic sentences: “This sounds like a no-brainer. I would love that.”

We hashed out the details over email and in several phone conversations, and across the next 15 months, the shape in the cloud became a real $81,625 in revenue. I could make the case that the fractional CMO engagement has been worth double or triple that amount because having the one put me in a position to say to new prospects, “I’m serving in this capacity for another client. Perhaps you’d be interested in a similar arrangement? Let’s discuss.”

We only need a few yeses.

We must train ourselves to notice possibilities because our clients often don’t come out and say, “Here’s my idea, and here’s my budget. I want you to run with it.” A giant blinking green arrow won’t be pointing the way to the opportunity. No, they make a passing remark about a need or gap, an upcoming change or challenge, a desire or frustration. You must sniff it out like a hound dog.

Another one of my CMO clients, Hudson, excels at this. He founded a small creative agency and starts conversations by pitching big, bold ideas to his clients, usually the CEO or CMO. Perhaps three or four times out of ten, the other person responds with interest: “That’s intriguing. Let’s discuss further.” Hudson estimates that $800,000 worth of the agency’s $1 million in billing over the last two years came directly from these pitches.

Hudson doesn’t wait for his clients to dream up ways to carve off more of their budget and hand it to him. He tells them what he wants to do. Even if the pitch doesn’t produce a project, Hudson positions himself as a strong strategic thinker and valuable partner.

Opportunity Hound = Paradigm Shift

Most of us spend most of our lives waiting to be told by parents, teachers, coaches, leaders, supervisors, and other authority figures and gatekeepers what to do next. Follow instructions. Color inside the lines. Initial there, there, and there.

Once we join the workforce, we grow accustomed to being short-order cooks: “Tell me what you want, and I’ll do it.”

Solopreneurship can be a bucket of water over the head because suddenly the structure, oversight, and accountability vanish. No one hands down clear, complete instructions. No one looks over your shoulder. No one evaluates your performance.

The freedom, autonomy, and flexibility are both exciting and stupefying. “Uh, what should I do next?” It’s all too easy to revert back to the reactive, sit-and-wait paradigm of a 9-to-5 employee when a proactive, go-and-find paradigm will serve us much better.

Now that I’ve been freelancing and consulting for fifteen years, I can attest that the one right playbook for building a profitable, satisfying independent career doesn’t exist. In a certain sense, you can do whatever you want, but no one can make you do anyone.

Go get in the way of opportunity.

This intoxicating freedom and optionality can be like a lotus flower that lulls us into complacency, yet if there’s one competency that will reward you again and again in the years to come, it’s being an Opportunity Hound. A mentor once advised me, “Go get in the way of opportunity.” The question is, am I? Are you?

What’s the work you really want to be doing? What’s the brand you’d be thrilled to work with? Are you putting yourself out there, exposing yourself to embarrassment, failure, or being ignored, and with your heart in your hand, saying, “Here’s what I want to do with you.”

A single yes can precipitate a career-altering project or relationship, and chances are, that opportunity isn’t going to pop up like a mushroom in your inbox. My friend Brennan Dunn talks about expanding the surface area of your luck.

Are you?

Practical Ways To Act Like an Opportunity Hound

I’m going to rattle off several things that have worked for me and for my clients:

1. Reach out to past clients once a quarter and book a complimentary strategy session. Send the four questions you want to cover in advance: “What’s going well?” “What isn’t going well?” “How we can work together more effectively?” “What’s on the horizon for you?” The last question is the one that can turn up opportunities you wouldn’t otherwise have heard about.
2. Create the work you want to get paid for and share it online. Canadian illustrator James White of Signalnoise created new movie posters for his favorite films ‘80s movies. Obviously, the production company for the original Karate Kid wasn't around to hire him, but Canon did. (Yeah, the camera company.)
3. Make something you like better. Designer Dustin Curtis thought the American Airlines website looked like a twice-dead opossum, so he redesigned it and wrote an open letter to the company. A UX designer at AA wrote him back, and the UX designer got fired an hour later. Then, the whole story got picked up by Fast Company. The controversy that Dustin's blog post generated has been good for his notoriety. Dustin has over 43,000 followers on Twitter and an insanely popular blog.
4. Write entertaining emails. No one reads their emails anymore, right? And if you do send an email, keep it short, right? Wrong. I heard about a sales guy at a large DNS management company who wrote long, personal, and goofy emails to prospective clients. Recipients found the emails entertaining, and the guy landed huge deals by breaking unspoken rules.
5. Take the moonshot. Think of a client you have or a brand you love. What’s an obvious need they have that you can fill? How would you go about it? What would the outcome be? Hudson, whom I mentioned earlier, creates short pitch decks of 10 slides or less and uses them to start the conversation around a big, bold idea he has. If you don’t know the decision-maker, you can poke around on LinkedIn or the company’s website and use an email discovery tool like Hunter.io to find the right email address. You may be a single pitch deck and email away from doing the most challenging and fulfilling work of your life. Take the moonshot.

Sniff out the most direct path.

Cold email outreach is exactly what I resisted for a LONG time. The very idea called up a host of limiting beliefs and arbitrary rules:

• “We all get enough email. Pop up on their radar in other ways first.”
• “People hate email. They’ll see you as a spammer.”
• “How awkward would it be if you actually met them later?!”
• “Nobody’s going to read a long email. Keep it short and sweet.”
• “You have to be uber-professional. Funny can only get you so far.”

What is it about freelancers and creators that compels us to take the least direct route to accomplishing our goals? (I’m asking the man in the mirror, not you.) You’d love to work with that company? Heaven forbid you email the marketing director. You’d love to be a guest on that podcast? Don’t reach out to the host. How gauche. You’d love for that brand to sponsor your event? The last thing you should do is send a video message to their Head of Partnerships on LinkedIn. Nope. Nuh-unh. Play it cool. Be so circumspect that she continues to not know you exist.

What would you do if you weren’t adhering to unspoken rules? Who would you love to work with? What would the project be? What’s the most direct path?

Sniff it out and see what happens.

Courting dream clients works.

So how do you go about doing this? Here are the first two steps:

1. Make a list of cool organizations, companies, or brands. Focus on ones you genuinely like. For example, I love to flyfish, so a few companies that make high-quality gear are at the top of my list.
2. Do some reconnoissance. How strong is their website, photography, copy, advertising, and social media presence? What do they do really well? How could they improve? Have they missed opportunities? Take detailed notes while you assess their strengths and weaknesses.
3. Find a big, bold idea. What can you help them do that’s of immense value?
4. Make and send a pitch. At the heart of courting clients successfully are two attributes: generosity and audacity. Sure, they might “steal” your freely given idea and use it without hiring you. Sure, the person you contact may ignore or reject you. Saddle up, buttercup. That’s life. Most people won’t take advantage of you, and it’s worth risking the one person who may for the one opportunity that can change your life.
5. Keep going. Remember, this is a numbers game. One big, bold idea out of ten is all you need.

The road to growth is paved with discomfort, and the only way around is straight through. Become an Opportunity Hound, and your future self will thank you.

When you’re ready, here are 3 ways I can help you:

1. Freelance Fixes. This short guide walks you through 6 small but important “fixes” that you can make to raise your income without working longer hours. People really seem to like it.
2. Morning Marketing Habit. This course will help you build an “always be marketing” practice, become less dependent on referrals, and proactively build the business you want with the clients you want. My own morning marketing habit has enabled me to consistently make  6 figures as a freelancer.
3. Clarity Session. It’s hard to read the label when you’re inside the bottle. I've done well over 100 of these 1:1 sessions with founders, solopreneurs, and freelancers who wanted guidance, a second opinion, or help creating a plan.