19-Step Cheat Sheet for Selling Strategy

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Table of Contents

• Avoid the second arrow
• Why now is the time to start selling strategy
• What all can “strategy” encompass?
• 19-Step Cheat Sheet for Selling Strategy

Selling strategy as a standalone offer transformed my freelance business in early 2016.

But the story really starts back in September 2015. I was burning down fast. I’d co-founded and invested $25,000 in Closeup.fm, a tech startup, and soon discovered that startups aren’t as cool in reality as they seem in theory, kind of like the way kids dream of being grownups then learn about bills, taxes, and other adult responsibilities.

Anyway, because I had so many responsibilities with the startup, I wasn’t putting nearly as much or nearly enough time into my freelance business, which still paid all my family’s bills.

Our finances had been dicey for months, but it wasn’t until we carried a balance on our credit card that I acknowledged how unstable and fragile our financial situation really was.

Avoid the second arrow

Carrying a balance may seem trivial, like a small burn. Put some ointment and a band-aid on it.

For me, that little bit of debt packed a big gut punch. When we’d finally paid off our credit cards and my wife’s school loans in August 2013, I’d been so proud. “Look, Ma, I’m finally learning my lessons and growing up! We’re finally getting ahead!”

I’d had some record-setting $20,000 and $30,000 months, but a mere two years later, I found myself back in the same situation of being low on cash and even lower on time. That history repeating experience shook my confidence. I felt like a failure as a husband, father, and provider. I felt plain stupid: How could I have let us get back into this position?

I don’t know if your mistakes with money or in business have ever caused you to doubt yourself, but I know for a fact that one of the biggest mistakes entrepreneurs can make is internalizing our failures.

Maybe you’re familiar with that Buddhist parable about two arrows? In life, we can’t always control the first arrow, the painful event, experience, or conversation, but we can control the second arrow, that is, how we respond. Pain is inevitable, but the ongoing suffering isn’t. It is often self-inflicted.

If I had a September 2015 do-over, I wouldn’t shoot myself with the second arrow. I wouldn’t compound the problem by telling myself a story that was only partly true and giving my confidence a black eye. Instead, I’d say “This unwanted event happened. It stings. How can I recognize my mistakes and address them with firm resolve while being charitable to myself?”

Why now is the time to start selling strategy

I share this story because, as I write this, I’m coming out of half a dozen conversations with freelancers, mostly writers, who told me one of two stories:

1. The market has gotten tougher, my earning is down, and I’m trying not to panic. My confidence has taken a hit.”
2. The market has gotten tougher, my earning is fine because I found a lucrative niche, and I’m trying to be grateful. However, I’m working too much. I’m tired. I’m burned out.”

Whether or not either scenario rings true for you, I’ll give you the same advice before sharing a 19-step process you can try immediately.

Here’s the advice: Swim up the value stream. Start selling the way you think, not just what you do; the head work, not just the hands work.

By charging for the way you think and advice you give, you accomplish several important things for yourself:

• You can dramatically increase your effective hourly rate (EHR) because the perceived value of thinking work tends to be much higher than hands work (copy, content, design, code, etc.)
• You make your business less fragile by becoming less dependent on a single skill or type of client.
• You give yourself more somethings to sell, which means you can sell something to more prospects.
• You reinforce your positioning as a leader and expert guide, not an order taker and generic vendor.
• You get paid to vet new clients before working with them on big projects.

Sidenote: Sometimes, it helps to see how other people are packaging up and selling their expertise. This collection of ideas will inspire you. If you want more ideas, you can check out these 26 ways to get paid for your advice.

What all can “strategy” encompass?

I use the word “strategy” incorrectly on purpose because the “s” fits in nicely with the 3 core offers that members of my Business Redesign group coaching program create. Strategy can encompass various types of head work:

• Strategy → What are you going to do and why?
• Diagnostic → What’s right? What’s wrong? What’s next?
• Audit → What’s happening? What insights can you glean?
• Ideation / Brainstorming → Want help coming up with fresh ideas?
• Planning → How will you achieve your goal?
• Training → What valuable knowledge and skills do I have that you want?
• Coaching → What goals can I help you achieve?
• Advisory → What advice, expertise, and perspective do you need?

You already do this, but you’re not charging for it.

Chances are, you already provide strategy in some form or fashion, but you’re just not charging for it.

For example, in 2015, when I started binge-listening to a podcast called Double Your Freelancing, the host, Brennan Dunn, talked about “project roadmapping.” He’s a software engineer, and he described the frustration I felt while doing marathon discovery sessions for free.

I’d invested many, many unpaid hours in helping disorganized, overly ambitious, or straight-up clueless prospects disgorge all their pains, needs, and ideas so that I could even send a proposal.

You’ve probably been there yourself. You poke around all that mess, trying to find something resembling a project so you canpin a price to it. You finally put together a whopper of a proposal that would deliver everything they said they needed, and they say, “We don’t have that kind of budget.”

“Super,” you think. “Thanks for wasting my time.”

Thanks to my startup, I was short on time and patience with that outcome. I was tall on bills. I needed a breakthrough.

Even if that hadn’t been the case, certain factors would have always limited my income potential, especially with writing projects:

• Time. Most implementation work is low leverage, non-hackable. (For example, nomatter how good I get at writing, good writing still takes time.) Our available timeinventory caps our earning potential.
• Energy. Freelance work requires significant creativity, focus, and energy. That’s especially true when your work focuses exclusively on implementation—for me, writing content and copy.
• Variability. The same implementation project for Client B can take more time than it did for Client A. Client B’s project has a much lower effective hourly rate. No matter how buttoned up your processes are, the risk is always there.
• Enthusiasm. The work product suffers when we’re tired or bored. Sure, we can force ourselves to finish, and our clients may not even notice a dip in quality. But we start to feel like we’re on a hamster wheel.

All of that was at play that fall, and in early 2016 I sold my first project roadmapping engagement. Once I got that first yes, I was hooked.

That experiment proved to be one of the most important (and lucrative) shifts I’ve made in my career. Selling strategy was how I crossed the bridge from Freelancing Land to Consulting Land. Selling strategy was how I started charging for all the ways I create value, not just writing and marketing projects.

Charge for ALL the ways you create value.

Freelancers and consultants have creative skills, and we also have these aptitudes:

• Lucid thinking & fresh ideas
• Research & synthesis capabilities
• Process, organization, & planning
• Ability to make new connections & produce new insights for clients
• Creative problem-solving, analysis, resourcefulness, & good judgment
• Domain expertise (i.e., specialized knowledge combined with knowing what will andwon’t work in advance)
• Valuable character and personality traits (i.e., honesty, curiosity, empathy)

Freelancers sell a certain deliverable like copywriting then use those aptitudes to deliver it. Consultants sell the aptitudes above then use writing to deliver them. Same aptitudes, only consultants makes a lot more money!

19-Step Cheat Sheet for Selling Strategy

Here’s a little cheat sheet you can use to start selling strategy for $9:

1. Pick the strategy flavor you think would be easiest for you—e.g., content roadmapping.
2. Pick a niche, or group of people who need this flavor—e.g., SaaS founders.
3. Define the outcomes the client gets—e.g., an organized list of her best stories, lessons, and blog topics, plus a clear action plan and sense of momentum.
4. Think back on past projects and list the questions that need to be answered for the client to get clarity—e.g., “What frustrates you about your industry?” Don’t be afraid to use ChatGPT and poach questions from people already doing this, too.
5. Turn the client’s obstacles and outcomes into a promise—e.g., “By the end of the session, you will have 24 of your best ideas organized into a writing and publishing schedule.”
6. Take 5 minutes to think through and write down the 5-8 steps of the process you’ll use in the session.
7. Decide how long you need for the session: 60 minutes, 90 minutes, 3 hours, whatever.
8. Put a price tag on the strategy session: What amount of money would you feel great about making for that amount of work?
9. Sign up for a free Calendly account and create the event—e.g., “24 of Your Best Post Ideas in 60 Minutes.”
10. Create a GDoc (same name as the event) and spend 20 minutes writing a crappy first draft of your offer, based on the 3 key pieces (promise, process, price).
11. Brainstorm a list of 10 people in your target audience you already know. (Be sure to check your LinkedIn connections.)
12. Reach out and ask if they’d be willing to shoot holes in your rough draft.
13. Use their feedback to iterate your offer.
14. Create a free public landing page using Notion. Or, simply send people to the GDoc and take payments via a free Stripe account and Stripe Link. Don’t overthink this step, and don’t waste time perfecting a web page when you should be validating this new offer.
15. Follow up with the 10 and ask, “Would you pay $XXX for this now? Why or why not?”
16. Close 2 of them if you can.
17. Find 50 more prospects on LinkedIn or get creative in how you identify them—e.g., SaaS-focused startup accelerators in the Southeast U.S.
18. Start one conversation a day. (Here are email templates you can customize.)
19. Pay attention to what wants to happen.

I hope you’ll try selling strategy. Getting started is the hardest part. Once you do, you’ll learn and gain confidence along the way.

When you’re ready for some help with creating your strategy offer, I have a 90-minute workshop for you. It’s $249. You can get all the details here, and pay here. I’ll then send you everything you need.

By the way, if you know another freelancer or consultant who really needs a breakthrough right now, please send this post to them.

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

1. Free Money. A pricing and money mindset guide for freelance creatives. If you’re unsure about your freelance pricing, this is the book for you.
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. Custom Business Roadmap. Gain clarity, confidence, and momentum in your freelance or consulting business.
4. Business Redesign. Raise your effective hourly rate, delegate with confidence, and free up 40 hours a month.
5. 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.