5 Freelance Community Conversations Too Good to Keep Secret

Freelancing doesn’t have to be lonely.

If you belong to an online freelance community, you have built-in camaraderie and, just as important, an on-demand mastermind group. You get instant access to the perspectives, insights, and advice of other freelancers and consultants.

To show what I mean, I took five recent conversations from inside the Freelance Cake Community and turned them into a highlight reel.

Use the ideas and questions at the end of each section to problem-solve in your own business.

1. Getting more freelance projects

What’s working right now for community members is 1) offline ideas and 2) online fundamentals.

Several members attended in-person events. They went in with a clear strategy and left with multiple leads.

Other members are running experiments with direct mail by sending letters, postcards, monthly and print newsletters. Our conversations revealed three main mistakes that freelancers make:

• Not being targeted enough with direct mail. It’s better to send mail 3 times to 20 or 30 highly researched prospects than to mail a less focused list of 100 people only once.
• Giving up too soon, that is, not sending mail multiple times.
• Not split-testing different hooks, wording, and CTAs.

Direct mail combined with phone calls can be a one-two punch, and we’ve got anecdotal evidence that direct mail can produce referrals, meaning that the person who received the letter told someone else.

Unsurprisingly, some recipients may receive a letter, hold onto it for months, and contact you much later. Or, they may check you out on LinkedIn before emailing or DMing you.

As for online fundamentals, members are nudging dormant clients, networking with other freelancers, and being consistent on LinkedIn.

If you stay consistent with them, these unremarkable tactics still bear fruit.

Questions: Are you proactively nudging dormant clients and networking with other freelancers? Who are 20 dream clients you’d love to work with? What if you hand-wrote a letter, then send a postcard, then a case study, and then called? Could that work?

2. Using a CRM

The consistency in outreach, networking, and follow-up mentioned above implies that you follow a system and a schedule.

Though it’s hard to imagine a strategy less sparkly and exciting than starting a handful of conversations each day, it’s also hard to imagine a more reliable way to drum up new work. I’ve written elsewhere about sales fundamentals and how regular inputs lead to regular outputs.

Put in enough sales actions, such as emails, LinkedIn messages, and calls, and you’ll get a lead. Once you figure out the mathematical relationship between the two, you’ll feel like you have more control over your business and finances.

Conversations in the community naturally turn to “What CRM are you using?”

Members are using PipeDrive, HubSpot, and Moxie, and one of my coaching clients likes a newer player, Wobaka.

If I may offer a bit of advice?

Before you pick a CRM, do the following:

• Write down exactly what you want the CRM to do and why.
• Email the support team for each CRM you’re considering and ask them if their tool can do what you need it to do.

Confirm your specific use case before you start using a CRM in earnest so that you don’t get so dazzled or distracted by cool features you won’t actually use that you miss the more important mismatch: The CRM lacks the core features you do need. I’ve been guilty of this!

Questions: Are you putting in enough sales actions to get your desired number of leads? How’s your math mathing? What’s the root problem, whether a big enough list of prospects or the daily habit? Are you making things easier on yourself by tracking actions in a CRM?

3. Deciding what to include in a new offer

It’s exciting when your focused marketing and business dev effort works. You have that discovery call that you definitely wouldn’t have booked if you’d failed to do X, Y, and Z last month.

But what if the startup asks for something slightly adjacent to what you’ve done in the past?

You could do it, of course. It’s in your wheelhouse. You do want the gig.

However, you don’t want to leave money on the table. You don’t want to overpromise either.

Situations like this crop up in the community several times a month, and honestly, I’m amazed at the depth and quality of feedback members get. Free communities and Reddit threads come nowhere close.

That’s the power of a good community. Positive spillover is real.

How members advise other members to tackle these situations varies.

The key is shrinking the amount of ambiguity and becoming more and more confident, in the scope, in the price, and in how you’d approach the slightly adjacent tasks and responsibilities.

Try this approach:

• Write down the part of the scope that is clear, predictable, and desirable.
• Write down the parts that are more ambiguous and journal through your concerns.
  • Which parts of the project aren’t yet well-defined?
  • Which tasks or responsibilities pose a risk because they can be a big time suck—e.g., “managing” a ghostwriting client’s LinkedIn posts?
  • Which parts are hard to predict because they’re fairly new to you?
  • Which parts simply aren’t desirable to you? Is subcontracting or delegating an option?
• De-risk your concerns and unknowns by planning for them. You’ll find that any anxiety you’re feeling will decrease along with the ambiguity.
  • For example, you may be less concerned about how managing the client’s LinkedIn posts might eat up too much time if you tell them that you’ll respond to comments for a maximum of 30 minutes per day.
• Add extra cushion (20%+) to your prices to account for any blind spots related to the less predictable part of the scope.
• Present the client with a couple of packages, including a lower price tier that doesn’t include the riskier, hard-to-predict stuff you’re less keen on and a higher tier that includes that riskier stuff.
• With retainers, do a three-month trial, not an open-ended commitment. At the end of 90 days, both parties can reevaluate the relationship.

Questions: When was the last time you sold something slightly adjacent to your past offers? What would you sell if you could sell anything? What would you charge for that? Who might be willing to buy that from you right now? How can you start that conversation?

4. Selling strategy as a standalone offer

The word “strategy” gets tossed around a lot, and though it’s true that selling strategy is a smart idea for freelancers, many of our clients don’t think they need it.

They may need fresh ideas or clarity. They may need advice from an expert. They may appreciate outside perspective on their plan or help with organizing their jumbled priorities into an actionable plan.

But most of them don’t roll out of bed in the morning, thinking, “Tralala, that’s it! Well-defined strategy will solve my stuckness problems!”

Various community members were getting tripped up by the word itself, “strategy,” so I asked one of them to sign up for a Hot Seat session.

We spent 30 minutes discussing how to sell “strategy as a standalone offer.”

Though we covered a lot in that time, I’ll try to summarize:

• Pick one audience and one outcome. For example, an editor might pick nonfiction authors and “honest, actionable feedback on your book concept and sample chapter.”
• Draft a one-page offer (name, who it’s for, outcomes, agenda, deliverables, timeline, price, call to action).
• Give it a name based on the audience’s identity and desired outcome (e.g., Author Book Idea Validation, SaaS Founder Growth Sprint, Agency Pivot Plan).
• Add a booking + payment link. For example, I use Moxie. Calendly works, too.
• Think about people already in front of you: current leads and clients who are vague, scattered, or “word-vomiting” on discovery calls. Are any of them candidates for this offer? If so, send it to them.
• Identify 5 current leads/clients who are fuzzy → invite them into the paid roadmap instead of more free calls.
• Block 2 dates for sprints; invite prospects to claim a slot.

“Strategy” isn’t a mystical deliverable. It’s paid advice about which path the client should take and why. It comes with a plan, which is how they’ll walk that path.

Speaking of, the client owns execution. You may help get them moving, but the results are their responsibility.

Further Reading: “12 Scenarios Where Selling Strategy Prevents Headaches” and “19-Step Cheat Sheet for Selling Strategy.”

Questions: Are you selling ideas, advice, or planning as a standalone offer? If not, what would it look like to package up your expertise and offer your ideas and the way you think? Which target audience seems the most ripe based on your specialized knowledge and perspective? Can you think of anyone who needs clarity or an actionable plan?

5. Turning bad days into good ones

Several members of the community have been through the ringer this year: looming divorce, deaths in the family, past trauma resurfacing, a battle with cancer, mental illness, and everything in between.

Ordinary events, such as a rough night of sleep or unfair email from a client, only add to the difficulty of showing up at our best.

The real trap is binary thinking. Either you show up at your best, or you’ve failed.

During an open-ended discussion on a Tuesday, various members weighed in on how they forget about their “best” and avoid showing up at their worst. Here’s an incomplete list of 10 go-to practices:

• Stay hydrated. Drink water to avoid compounding the problem.
• Feed your brain. Choose protein and fiber over sugar to avoid crashes.
• Name it. Spend 10 minutes journaling: “Today feels ___ because ___.” Take out your head trash.
• Walk. A 20-minute walk, especially outdoors, can reset mood and focus.
• Practice gratitude. Write three specific things you’re grateful for, even if you’re scraping the bottom of the barrel.
• Minimum Viable Progress. Pick one 15-minute task that moves a priority forward; set a timer and start.
• Keep your promises. If possible, meet all your deadlines and commitments.
• Protect your reputation. If you truly can’t deliver quality, message the client early. Be honest about not being at your best. Propose a new, realistic time.
• Enjoy beauty. Whether it’s music, a poem, or your favorite park, seek out what reliably lifts you.
• Encourage two people. Tell a couple of people what you admire about them.

Bad days can become good days. They don’t always end how they started.

Having a Lemonade Protocol makes that turnaround more likely.

Borrow a play from Farnam Street founder Shane Parrish’s playbook: "Instead of always trying to be your best, ask yourself how to avoid being at your worst.”

Questions: What can you do now to prepare for your next bad day? What belongs in your protocol?

Before you go…

Let me invite you to apply to join the Freelance Cake Community. It’s a group of more established, advanced freelancers.

One member named Michelle, had this to say:

“I’m just so impressed by the quality of the conversation that’s happening in the group. The in-depth questions, experiments, and thoughts being shared are just so refreshing. In the other communities I’m part of it’s all beginner questions, which is fine, but it’s awesome to find a more advanced space where it’s OK to ask more advanced questions.”

Here’s a little more about the community:

• Each week, we do live group coaching and live coworking.
• You get access to a massive Resource Library and obviously the community itself which we host using Circle.
• Of course, the people are the best part of this. It really helps to surround yourself with smart, accomplished, and optimistic people who are out there taking risks and building businesses they really love.

If joining interests you, go here to apply.

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Other 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. 1:1 Coaching. Gain clarity, confidence, and momentum in your freelance or consulting business.
4. 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.