Freelance Cake

Getting laid off twice might not sound like the beginning of a story about job security. For Satta Sarmah Hightower, it was.

Satta started freelancing in 2014 after back-to-back layoffs. She figured freelancing would tide her over until she found another full-time job. Twelve years later, she has built a multi-seven-figure solo business.

And strangely enough, she now considers freelancing the most secure job she’s ever had.

Why?

A layoff can erase 100% of your income overnight. A well-built freelance business gives you diversification — across clients, relationships, services, and opportunities. But resilience like that doesn’t happen accidentally.

In this conversation, Satta walks me through seven lessons she learned while building her business:

1. Treat your business like a business.
2. Choose your niche wisely.
3. Always be marketing.
4. Don’t just date your clients. Marry them.
5. Repurpose profits into future revenue.
6. Create a business continuity plan.
7. Go with the season you’re in.

What I appreciate about Satta is that none of these lessons depend on working yourself into the ground.

Quite the opposite.

We talk about setting boundaries even when losing a client scares you. We talk about choosing a niche based not only on what interests you, but also on demand and profitability. We talk about why your best source of future revenue may be the clients who already know and trust you. Satta also explains her “W-2 prevention plan”: a pre-decided set of actions she can take if a big client disappears or revenue suddenly drops.

Because panic is a lousy business strategy.

Finally, we talk about something that tends to disappear from conversations about seven-figure businesses: seasons.

Sometimes you can push.

Sometimes your family, health, caregiving responsibilities, or plain old life need more from you. Building for the long game means knowing the difference.

Note: This conversation was originally recorded for the Advanced Freelancers Summit in May 2026.

Key Points

• Treat your business like a business: Stop acting like a hired hand waiting for clients to dictate your schedule. Build systems, processes, financial discipline, boundaries, and diversified marketing into the business.
• Choose your niche based on more than passion: Satta followed demand toward B2B tech content and used her journalism background as a differentiator. She even studies current job descriptions to see which skills clients are hiring for now.
• Always be marketing: Don’t wait until a client disappears and your nervous system catches fire. Marketing works better as an ongoing habit than an emergency response.
• Turn clients into long-term relationships: Look for gaps you can fill, educate clients about the other problems you solve, and stay in touch. Your clients are busy. They aren’t necessarily going to remember to call you.
• Reinvest in yourself: Satta regrets being too conservative with her resources early in her career. Today, she deliberately puts profits toward future growth opportunities, including her book, The Forever Freelancer.
• Create a W-2 prevention plan: Decide in advance what you’ll do if revenue drops 50% or an anchor client disappears. Satta’s plan includes sending LOIs, checking in with current and dormant clients, and activating her network.
• Go with the season you’re in: There are seasons for pushing and seasons for pulling back. A sustainable business should accommodate both.

Notable Quotes

• “I’ve had experience over the last 12 years that proves to me that being proactive is the path to sustainable business. If I wasn’t and if I just sat around and moped when things weren’t well, and I’ve had times even in recent years where things haven’t gone the way I thought they would go, but I was able to turn them around because I just did what I knew worked.”
• “Don’t just date your clients, marry them. And by that, I mean you want to build long term relationships with clients, whether that’s through retainers or they become anchor clients. You don’t want just one assignments because I think I really saw income growth when I started to have those long term relationships and engagements with clients.”
• “People are busy. They’re not thinking about you. You’ve heard of demand generation marketing where you are everywhere your potential customers are, even when they’re not ready to buy… So it’s sort of like the same principle. You’re like omnipotent in a way. And then all of a sudden when there’s a project, because you’ve been in their feed or you’ve sent them that touch base email, they’re like, oh, you’re the first person they think.”
• “Go with the season you’re in. So rest, recharge and play the long game. This is especially important for parents and caregivers. I think there will be there are seasons in life and there are seasons in freelancing. There will be times where you can work a lot and really pound it out and really grow your business really fast. And there’ll be times where you can’t, where life takes over. You have to give yourself grace and realize that it’s a continuum here.”

Resources Mentioned

• Check out Satta’s website: http://sattasarmah.com/
• Connect with Satta on LinkedIn: https://www.linkedin.com/in/sattasarmahhightower/
• Learn about Satta’s book, The Forever Freelancer: https://www.sattasarmah.com/book
• Listen to Satta’s previous Freelance Cake episode: http://freelancecake.com/podcast/from-accidental-freelancer-to-strategic-business-owner-with-satta-sarmah-hightower
• Read the 15 Ways to Get Clients Fast essay: https://www.freelancecake.com/blog/15-ways-to-get-clients-fast
• Check out the Freelance Cake Community: https://www.freelancecake.com/community

John Jonas hired his first full-time worker in the Philippines in 2005. Within a couple of weeks, he says it felt like there were suddenly “two of me.”

That experience eventually led John to create OnlineJobs.ph, and today he has roughly 60 people working for him in the Philippines. Some of the people he hired nearly 20 years ago are still on his team.

But this conversation isn’t really about finding someone to manage your calendar. It’s about leverage.

John prefers the term Online Filipino Specialist (OFS) because the people he hires aren’t limited to traditional VA work. His team includes developers, content specialists, marketers, and other people responsible for business-critical functions.

And that distinction matters for freelancers. At some point, doing everything yourself stops being evidence that you’re capable and starts being the reason your business can’t grow.

John’s philosophy is refreshingly simple: Getting it done is more important than getting it done your way.

Yes, someone else may make mistakes. Yes, training them will require time. Yes, you may currently be terrible at delegation.

John’s response to that last objection is basically: Okay. Then learn.

Because staying buried in email, client work, admin, marketing, and every other detail of the business leaves very little room for the work only you can do: thinking, selling, strategizing, and leading. John says he has spent years working around 15 hours per week precisely because his team gives him room for that higher-value work.

We also get into AI.

John is hardly anti-AI. His entire team uses it. But his argument is that AI and human talent don’t have to be competitors. Use AI for what AI does well. Use talented people for everything else. Most importantly, don’t spend the next three years waiting for some magical agent to run your business while you remain the bottleneck today.

Finally, John walks through his hiring process, including why he prefers email before video interviews, what he looks for in a test task, and the surprisingly important question he asks when an employee isn’t performing:

What did I do wrong?

The employers John sees succeed take responsibility for their instructions, communication, and leadership before assuming the person they hired is lazy or incompetent. They also remember that the person on the other side of the screen is exactly that—a person, not an expendable commodity.

If success has somehow made your freelance business heavier instead of lighter, this conversation may help you see what’s missing.

Maybe you don’t need to work harder. Maybe you need help.

Note: This conversation was originally recorded for the Advanced Freelancers Summit in May 2026.

Key Points

• Doing everything yourself eventually becomes the bottleneck. The skills that helped you build a successful freelance business can trap you in its day-to-day details if you never learn to delegate.
• Think beyond the traditional VA. John calls the people he hires Online Filipino Specialists because they can own specialized and business-critical work—not just calendars and data entry.
• Getting it done beats getting it done your way. Perfectionism and control can masquerade as quality standards while quietly keeping everything on your plate.
• Training is an investment, not an instant time saver. John readily admits that a new hire may consume more time than they save during the first month. The payoff comes when great people stick around long enough for that investment to compound.
• Delegate where your time is actually going. Instead of automatically outsourcing the task you dislike most, John recommends looking at what consumes the most time and figuring out how another person can support or own it.
• Hiring can force you to think like a CEO. Committing to another person creates pressure to find meaningful work for them—and gives you room to spend more time on sales, strategy, systems, and growth.
• AI and people aren't mutually exclusive. John’s team uses AI extensively. His point is to use the technology to make good people better rather than assuming AI has already eliminated the need for people.
• Test for collaboration, not just technical ability. John uses test tasks partly to see whether candidates ask smart questions, clarify ambiguity, and work well with him—not merely whether they can produce the deliverable.
• When something goes wrong, check your instructions first. One of John’s biggest distinctions between successful and unsuccessful employers is whether they immediately blame the worker or first examine their own communication and leadership.

Notable Quotes

Resources Mentioned

• Check out OnlineJobs.ph: https://v2.onlinejobs.ph/
• Follow John Jonas on LinkedIn: https://www.linkedin.com/in/john-jonas-41128b/
• Get John’s free Quick Start Guide: https://www.onevaaway.com/quickstartguide

What happens when you’ve already built a successful freelance business?

You could keep doing what works. Or you could ask a more interesting question: What else might be possible?

Ross Simmonds grew up in a small community in Nova Scotia without an elite marketing network or proximity to the usual centers of opportunity. He went on to build a multiple six-figure freelance business, found the B2B content marketing agency Foundation, build a 50+ person team, write Create Once, Distribute Forever, and become CEO of Distribution.ai.

Ross doesn’t describe that path as a series of perfectly planned career moves.

He describes it as compounding.

He kept creating. Experimenting. Learning. Meeting people. Doing good work. Putting ideas onto the internet and seeing what came back.

One of his operating beliefs is simple: Give value to the internet, and the internet will give value back.

That philosophy becomes especially interesting when we talk about content.

Ross believes most content collects dust for a deeply human reason. We tell ourselves we’re too busy to promote our work. He thinks we’re mostly afraid.

Afraid of repeating ourselves. Afraid of looking like a try-hard. Afraid of annoying people. Afraid somebody will disagree with us in public.

So we press publish, get the nice little dopamine hit from finishing something, and immediately start creating the next thing.

Ross offers a different frame: Publish is halftime.

The second half is distribution.

Take the podcast, article, case study, video, or idea you worked hard to create and keep finding useful ways to put it in front of the right people. Because being excellent and being known for your excellence are two different things.

We also talk about video as an underused opportunity, how to participate in communities like Reddit without barging in like a marketer with muddy shoes, why public speaking created enormous leverage for Ross, and what AI does—and does not—change about expertise.

Ross’s AI take is refreshingly non-apocalyptic: AI makes good people faster at good work. It makes exceptional people faster at exceptional work. But it cannot manufacture the taste and judgment you never developed.

Your craft still matters.

So does doing what you said you would do. So does becoming a slightly better human tomorrow than you were today.

That’s a much bigger conversation than writing better LinkedIn hooks, and I think that’s exactly why it belongs here.

Note: This conversation was originally recorded for the Advanced Freelancers Summit in May 2026.

Key Points

• Your current ceiling may not be permanent. Ross grew his career from a small town by refusing to assume geography or a lack of connections determined what was possible.
• Think in compounding, not career ladders. Freelancing, agency ownership, investing, software, writing, and speaking became interconnected layers rather than isolated career moves.
• “Publish” is halftime. Creating the asset is only the first half of the job. Distribution is what gives the work a chance to produce a return.
• Fear is a distribution problem. Freelancers often say they lack time to promote themselves when the deeper issue is fear of judgment, repetition, or being seen trying.
• Distribution is a competitive advantage. Great work alone doesn’t guarantee reach. The freelancer who consistently gets strong ideas in front of the right people can outperform someone with equal—or even greater—technical skill.
• Show people how good you are. Long-form content, case studies, videos, podcasts, and thoughtful analysis can demonstrate how you think before a prospect ever talks to you.
• Video and niche communities deserve attention. Ross sees video as a powerful relationship-building format and encourages freelancers to engage genuinely in communities like Reddit rather than treating them as another billboard.
• AI accelerates expertise. It doesn’t replace it. Good judgment, taste, fundamentals, and subject-matter knowledge become more valuable when powerful tools make execution easier.
• Public speaking creates authority at scale. Ross went from being nicknamed “Shy Ross” to using speaking as a way to build rapport, credibility, relationships, and business opportunities.
• Getting better is bigger than business. Ross closes with a reminder that growth isn’t only about becoming a better marketer. It’s about improving how you serve clients, teams, family, and the people around you.

Notable Quotes

Resources Mentioned

• Follow Ross Simmonds on LinkedIn: https://www.linkedin.com/in/rosssimmonds/
• Check out his website: https://rosssimmonds.com/
• Check out Foundation: https://foundationinc.co/
• Check out Distribution: https://www.distribution.ai/
• Listen to The Ross Simmonds Show: https://podcasts.apple.com/ph/podcast/the-ross-simmonds-show/id1653650073
• Check out the Freelance Cake Community (for established freelancers eager for sustainable growth): https://www.freelancecake.com/community

What if you didn’t need to create more content to find more clients?

Kendall Cherry doubled her freelance income by turning her best old posts, emails, stories, and case studies into a sales ecosystem that could keep working while she served clients, wrote a book, or stepped away from her business.

In this episode, Kendall explains how to find the old content that still has selling power, map it to each stage of the buyer journey, attract actual buyers with a services guide, and replace hour-long discovery calls with better inquiry forms and refreshingly simple proposals.

A quick note: This conversation originally aired as part of the Advanced Freelancer Summit (May 2026). It was too useful to leave inside the summit, so we’re republishing it here.

Key Points

• Quality beats freshness: New content is not automatically better content. Strong stories and sales ideas can keep performing long after their original publication date.
• Build a greatest-hits library: Kendall reviewed her past posts and emails, identified the strongest pieces, and collected them in an 83-page content bank.
• Use real signals: Engagement data, email replies, inquiries, client language, and remembered sales conversations can help you decide which content deserves another life.
• Treat content like a funnel: Top-of-funnel stories create resonance, middle-of-funnel content develops demand, and bottom-of-funnel case studies reduce buying uncertainty.
• Write content that qualifies leads: Listicles and “day in the life” stories help prospects recognize their own problems and signal which messages matter most to them.
• Publish more case studies: Kendall recommends a case study every two weeks on social media and at least once a month by email.
• Qualitative proof still counts: A case study does not need a dramatic revenue number. Confidence, clarity, speed, relief, and a better process are legitimate transformations.
• Separate relationship-building and direct selling: Kendall sends a direct sales email on Mondays and a more personal Wallflower Fridays newsletter at the end of the week.
• Use your services guide as a lead magnet: A clear guide can attract buyers, communicate pricing, answer objections, and establish working boundaries before an inquiry arrives.
• Let inquiry forms do the early discovery: Better questions can qualify prospects and reduce hour-long sales calls to short conversations—or eliminate the call altogether.
• Keep proposals simple: Scope, timeline, price, payment options, and a next step can often live in the body of an email.
• Build the system for a reason: Content leverage creates time for client delivery, family, rest, writing, new offers, and the bigger work that matters to you.

Notable Quotes

Resources Mentioned

• Kendall Cherry’s website: https://kendallcherry.com
• Kendall’s Sales Ecosystem Playbook: https://kendallcherry.com/playbook
• Check out The Greenhouse program guide: https://findthegreenhouse.com/
• Connect with Kendall on LinkedIn: https://www.linkedin.com/in/kendall-cherry/
• Check out the Freelance Cake Community: https://www.freelancecake.com/community

At some point in your freelance career, you start wondering whether the next level requires another person.

Maybe you’re booked out. Maybe too much of your week disappears into work that drains you. Or maybe you’re tired of being the person who must write, review, approve, fix, and send everything.

Hiring sounds like the obvious solution.

Unfortunately, a rushed hire can take a manageable problem and give it access to your clients, your calendar, and your bank account.

In this episode, I talk with Michal Eisik, an agency founder and the creator of ScaleTribe, about how advanced freelancers can hire without creating a fresh layer of chaos. Michal has grown her own agency from a solo operation into a global five-person team. She has also mentored more than 600 freelancers through CopyTribe, Profitable Freelancer, and ScaleTribe.

She knows firsthand that most hiring mistakes happen before the job is posted. People get overwhelmed. They need help yesterday. Then they hire the first available person who seems smart, pleasant, and reasonably competent.

That person may be excellent. They may also be excellent at the wrong things.

Michal explains why you should first get clear on your motivation. Are you trying to break through a revenue ceiling? Buy back time? Escape draining work? Move from execution into strategy and leadership?

Your answer changes the role you should create and the person you should look for.

We also discuss Michal’s “zone of drag”: the work that drains your energy, slows you down, or prevents you from focusing on more valuable activities. Your zone of drag can show you where to start, but “I hate this task” isn’t always a good enough reason to throw it at someone else.

You still need enough familiarity with the work to define success, create a useful brief, and recognize quality when you see it. Otherwise, you’re left with blind trust or micromanagement.

Neither one buys back much time.

Michal shares a practical process for lowering the risk:

• Define the responsibilities, outcomes, skills, and personal qualities the role requires.
• Ask candidates for three relevant samples, not a giant portfolio scavenger hunt.
• Start with a small, paid test project before handing over a major deadline.
• Create a clear brief so the person doesn’t need telepathy to succeed.
• Review larger projects at the 30%, 60%, and 90% stages.
• Give direct feedback while also pointing out what the person should continue doing well.

We also talk about the replacement ladder and why administrative work is often a sensible place to start. Often—not always.

Michal recommends tracking your time and looking at your actual business instead of blindly following an online formula. If admin takes two hours a week while delivery consumes thirty, a junior practitioner may buy back more meaningful time than a VA.

Then there is the management part.

Hiring someone does not automatically remove you as the bottleneck. You can build a team and still become the “approver of everything,” where every email, decision, and deliverable waits for your blessing.

To move beyond that role, you have to let capable people make decisions. You have to accept that most mistakes are not fatal. And you have to build a culture where people communicate problems quickly, own the outcome, and learn from what happened.

Finally, Michal gets candid about the numbers.

Hiring is not a productivity trick. It is an investment. You need predictable revenue, healthy margins, pricing that can support good talent, and enough room in your calendar to train the person. Michal says the first month is usually training-heavy, the second still contains plenty of questions, and meaningful return on the hire often begins around month three.

You cannot hire someone on Monday and disappear until the gorgeous finished work arrives.

Rude, but useful.

If you’re considering a VA, subcontractor, junior practitioner, project manager, or your first full-time team member, this conversation will help you replace guessing with a more thoughtful plan.

Key Points

• Start with your motivation: The right hire depends on whether you want more revenue, more time, relief from draining tasks, or a move into strategy and leadership.
• Audit your zone of drag: Identify the recurring work that drains you, slows you down, or keeps you away from higher-value responsibilities.
• Define the role before finding the person: Clarify the work they will own, the outcomes they will produce, and the skills and qualities they need.
• Do not panic-hire: Availability and general competence do not guarantee fit for the specific role your business requires.
• Vet with relevant evidence: Ask for three relevant samples and an explanation of why each one applies to your project.
• Use paid test projects: Start small, contained, and low-stakes before trusting someone with important client work.
• Create useful feedback loops: Review work at the 30%, 60%, and 90% stages so the person can course-correct before the end.
• Avoid becoming the approver of everything: Decide what truly needs your review and allow team members to take ownership of nonfatal decisions.
• Expect a training period: Plan for roughly three months before a new hire begins producing a meaningful return.
• Check your financial readiness: Predictable revenue, sufficient margins, and appropriate pricing matter more once you are supporting a team.
• Treat hiring like a CEO decision: Building something bigger than yourself involves risk, management, investment, and the possibility that you will get a few things wrong.

Notable Quotes

Resources Mentioned

• Michal Eisik’s website: http://michaleisik.com/
• Connect with Michal on LinkedIn: https://www.linkedin.com/in/michaleisik
• Watch the free Hire Without the Backfire training: https://www.michaleisik.com/opt-in/scale-webinar-ac
• Check out the Freelance Cake Community: https://...

Dustin Riechmann went from traffic engineer to marketing consultant to meat stick entrepreneur to founder of 7-Figure Leap.

Yes, meat sticks.

After COVID wiped out many of his local consulting clients and stopped the in-person trade show strategy that had been growing his e-commerce brand, Dustin got on a podcast. That one move helped him grow the meat stick company to seven figures, get into Walmart, and eventually build a coaching business around strategic podcast guesting.

This conversation is not about “getting your name out there,” which is one of those phrases that sounds useful until you try to pay your mortgage with exposure.

Dustin makes a much more precise claim: podcast guesting can become a real revenue channel for freelancers, consultants, coaches, and agency owners who treat it with consistency and intention.

His basic math is simple: If the right podcast interview produces an average of $2,000 in sales, and you do one good interview a week for 50 weeks, that’s $100,000.

But the more interesting part is what happens after the interview.

You build relationships with hosts.

You get introduced to other guests.

You create repurposable content.

You sharpen your stories.

You become easier to trust.

That’s the flywheel.

Dustin also breaks down his five-part framework: purpose, plan, pitch, perform, and profit. We spend time on why “purpose” comes before choosing shows, how to write a pitch that doesn’t smell like AI-generated oatmeal, why smaller podcasts can be wildly profitable, and which three stories freelancers should prepare before showing up as a guest.

If you want a more predictable way to build authority, start better relationships, and generate opportunities without relying entirely on referrals or social media, this episode will give you a practical place to start.

Key Points

• Podcast guesting is not just exposure: Dustin argues that strategic guesting can become a measurable business development channel when freelancers treat it like a system.
• The $100K math is simple, but not magic: One relevant interview per week, multiplied by an average of $2,000 in sales per interview, creates the basic path to $100,000.
• Consistency beats dabbling: Showing up on one or two podcasts and hoping for fireworks is not a strategy. The results come from repeated reps, better stories, and compounding relationships.
• Smaller niche podcasts can outperform bigger shows: Dustin explains why a small, trusted, highly relevant audience can be more valuable than a massive but less targeted one.
• Podcast interviews compress trust: The long-form, conversational format helps listeners get to know you faster, especially because the host has already earned their trust.
• Purpose comes before the podcast list: Before pitching shows, Dustin recommends getting clear on the transformation you provide and who you provide it for.
• Your pitch needs a relational anchor: A good pitch is not a spray-and-pray email. It should show real familiarity with the host, explain what’s in it for the audience, and make a clear ask.
• Great guests prepare three stories: Dustin recommends having an origin story, an authority story, and an “average Jane” story that proves the method can work for regular people too.
• A clear CTA matters: Freelancers with custom offers do not need to sell everything from the interview. Dustin recommends one clear next step, such as a playbook, quiz, assessment, or other opt-in that can help sort people after they raise their hand.
• Relationships create the real upside: The direct leads matter, but the host relationships, guest networks, partnerships, referrals, and repurposed content can become even more valuable over time.

Notable Quotes

Resources Mentioned

• Playbook: https://go.7figureleap.com/playbook
• Website: https://7figureleap.com/
• LinkedIn: https://www.linkedin.com/in/dustinriechmann

What does it actually take to create monthly recurring revenue with high-ticket freelance clients?

In this episode, Austin talks with Amanda Northcutt about the shift from project-based freelancing to premium retainers, advisory work, and long-term client engagements. Amanda explains why doing great work is not enough, why generalists struggle to command premium fees, and why high-ticket MRR starts with positioning, proof, methodology, voice-of-customer research, and offers that are built around outcomes instead of hours.

Listen to the full conversation.

Key Points

• MRR requires more than a retainer label: Monthly recurring revenue works when the client understands the ongoing value, not when you simply repackage random tasks into a monthly fee.
• High-ticket clients pay for outcomes: Amanda emphasizes pricing based on transformation, value, and expertise rather than effort or hours.
• The expert’s dilemma causes undercharging: Freelancers often undervalue work that feels easy because they forget clients are paying for years of judgment and pattern recognition.
• Generalists have a harder time selling premium retainers: If you are for everyone, you become easier to compare, replace, and negotiate down.
• Five things need to be true: Amanda names positioning, ideal clients, methodology, product ladder, and client acquisition as essential ingredients for a stronger recurring revenue business.
• Your methodology is the linchpin: A clear method helps clients understand what you do, why it works, and why the engagement should continue.
• Voice-of-customer research sharpens the offer: Amanda recommends talking to best-fit prospects to learn how they describe their problems, what those problems cost, and what language will make your offer feel relevant.
• Brain work beats endless hands work: Advisory, coaching, consulting, and fractional support can create higher leverage than retainers stuffed with time-consuming deliverables.
• Good fences prevent scope creep goblins: Long-term engagements need clear containers, outcomes, boundaries, and expectations.
• The best MRR offers create stickiness: Quarterly priorities, access, accountability, relationships, measurable results, and strategic guidance make you harder to replace.

Notable Quotes

• “You should be pricing your services based on the value and outcomes and transformation that you’re providing to your client, not the inputs that you put in.”
• “If you are the freelancer that is for all people at all times that will solve any problems because you’re this amazing generalist, you are a commodity... If you’re for everybody, you’re actually for nobody.”
• “Your highest leverage and what you will get paid the most for, counterintuitively, is brain work.”
• “We always want to decouple our time inputs from our money outputs.”
• “The purpose [of longer consulting engagements] is to create predictable recurring revenue over a long period of months and also to protect yourself and prevent scope creep.”

Resources Mentioned

• Amanda Northcutt on LinkedIn: https://www.linkedin.com/in/northcuttamanda/
• Amanda’s newsletter, Get the Level: https://welevelupcreators.com/
• Amanda’s email: [email protected]
• Freelance Cake Community: https://freelancecake.com/community
• Nir Eyal’s book, Beyond Belief: https://www.nirandfar.com/beyond-belief/

Hannah Soto didn’t set out to build a production company. She saw problems in her industry. People below a certain title were treated poorly. Productions were inefficient. Systems were messy. So she did what many capable, quietly ambitious freelancers do: She fixed what was broken.

That decision eventually became Aridia, a production company that worked with major clients like Apple, Coca-Cola, and the Olympics.

Not bad for an accidental business.

But this episode is not a shiny “look how big the business got” story. That would be too easy. Also, a little boring. This conversation is about what happens when the business you built starts asking for a version of you that you no longer want to be.

Hannah and Austin talk about growth, identity, client approval, excellence versus perfection, and the cost of staying in a business model simply because it still works on paper.

Hannah shares how one difficult international production exposed how much of her worth was tied to client approval. She had done everything she could to fix the situation. She spent money, energy, time, and health trying to make the client happy again. And then she realized something brutal and freeing: She didn’t even want to work with that client again.

That moment became part of a much bigger shift. Hannah began untangling her value from her work, rethinking what success actually meant, and eventually moving more deeply into coaching.

This episode is for the freelancer, consultant, or creative entrepreneur who has built something real but feels the tension of an old model getting too tight around the shoulders. Like a business blazer from 2017. Technically still wearable. Spiritually suspicious.

Key Points

• Accidental entrepreneurship: Hannah started by solving obvious problems in production, especially around how people were treated and how systems were run.
• Brand name versus personal name: Hannah explains why choosing a company name gave the business room to grow beyond her, while still allowing her personal brand to build trust.
• Excellence is not perfection: Growing up with a strong family mantra around excellence shaped Hannah’s drive, but also created pressure she later had to untangle.
• When client approval becomes a trap: Hannah shares the painful story of a project where she gave everything to win back a client’s approval and still couldn’t get it.
• Not every client deserves access: Austin and Hannah discuss the difference between generous, honest clients and clients who take advantage of vulnerability.
• The cost of staying: Hannah’s key question — “What is it costing me to stay?” — becomes a powerful filter for any freelancer considering a pivot.
• Momentum is not alignment: Just because a business is moving does not mean it is moving in the right direction.
• Work beside life, not above it: Hannah describes the difference between building life around work and letting work sit beside health, marriage, friendships, and purpose.
• You may never feel ready: For freelancers who want to pivot, Hannah suggests clarifying the bare minimum needed, knowing the vision, and accepting that readiness may never arrive with a little gift basket.
• Being before doing: In her coaching work, Hannah helps entrepreneurs explore who they need to become, not just what they need to achieve.

Notable Quotes

“I don’t know yet is a really powerful answer.”

“Fear is going to keep us smaller.”

“What is it costing me to stay?”

“My work sits beside my life. It is not connected to my value or my worth.”

“A company is a reflection of the founder.”
"At some point, we just need to decide, I want what is on the other side of this discomfort more than I want comfort. And so what am I willing to embrace for sake of that vision?"

“There will always be an excuse if you look for it. So just start.”

Resources Mentioned

• Hannah Soto on Instagram: https://www.instagram.com/hellohannahsoto/
• Arridia: https://www.arridiagroup.com/
• Email Hannah at hannah[AT]lovingthegap[DOT]com (Be sure to mention that you heard about it here on the Freelance Cake Podcast so she knows where you came from)
• Freelance Cake Community: freelancecake.com/community
• Book 1:1 coaching with Austin: https://www.freelancecake.com/freelance-business-coaching

Satta Sarmah Hightower opens up about the evolution from being a skilled freelancer who took good opportunities as they came… to becoming a more intentional business owner who chooses work based on where she wants to go.

At first, she did what many freelancers do: she followed the money. After layoffs and instability, survival mode made that feel sensible. But over time, she realized that good income and a solid client base were not the same thing as strategic growth.

One of the most useful parts of this conversation is Satta’s “monkey bar strategy.”

Instead of trying to leap blindly into a brand-new niche, she explains how freelancers can use adjacent experience to move from one bar to the next — from healthcare to healthcare tech, from financial services to fintech, and from familiar work into more valuable, better-aligned opportunities.

We also get into the identity shift that often separates advanced freelancers from plateaued ones.

Satta talks about what changed when she stopped primarily seeing herself as a writer and started thinking like a solopreneur and business owner. That shift made her more intentional about what work to accept, how to position herself, and how each project could support the business she wanted six months down the road — not just the invoice she wanted this month.

There’s also a strong thread in this episode around sustainable growth.

Growth, for Satta, does not mean going wider and building a giant machine she does not want. It means going narrower, deeper, and getting clearer on what “enough” looks like. We talk about mindset, gratitude, recovery time, and the planning practices that help experienced freelancers grow without burning down fast.

And if you’ve been thinking beyond client work, you’ll appreciate the final part of the conversation about IP.

Satta shares why she wrote The Forever Freelancer, how she thinks about intellectual property as a durable asset, and how building assets like books, newsletters, and other owned work can expand what a solo business becomes over time.

This one is for freelancers who are no longer asking, “How do I get work?” and are now asking better questions:

What kind of business am I actually building?

What direction am I choosing?

And how do I grow on purpose?

Key Points

• From survival mode to strategy: Satta admits she was not especially strategic in the early years. She was following the money, building from available opportunities, and doing what many freelancers do after instability: taking solid work when it appeared.
• The monkey bar strategy: Rather than reinventing yourself from scratch, use adjacent experience to move into stronger niches and better-paid categories of work. Think bar to bar, not cliff dive to cliff dive.
• The identity shift matters: Advanced freelancers often hit a ceiling when they keep identifying only with their craft. Satta’s growth accelerated when she began to think of herself as a business owner and solopreneur, not merely a freelance writer.
• Intentionality changes decisions: Once she embraced that business-owner identity, she became more deliberate about what work to accept and how each engagement served her longer-term trajectory.
• Gradual change is underrated: Satta makes a strong case for evolving slowly and intelligently rather than blowing up your whole business in the name of “transformation.”
• Growth is not always bigger: For her, growth means going narrower and deeper, not building an agency or chasing “more, more, more.”
• Mindset and recovery are business tools: Gratitude, space to reflect, and her “For Me Fridays” practice all support sustainability and clearheaded decisions.

Notable Quotes

• “It’s about evolving from reactive freelancing into strategic business ownership.”
• “I own my trajectory and my business growth and my professional growth.”
• “Growth, at least for me at this stage, it doesn’t necessarily mean going wider. It means going narrower and going deeper.”
• “You have to know what your enough is and you have to know what growth looks like for you.”
• “You need to treat your business like a business.”

Resources Mentioned

• Satta’s book listing for preorder: https://tinyurl.com/sm9z59my 
• Satta's Book landing page to subscribe for updates: https://www.sattasarmah.com/book
• Satta's Instagram: @sattasarmahhightower
• Satta's TikTok: @sattasarmahhightower
• Substack: https://substack.com/@sattasarmahhightower‍
• Freelance Cake Community: freelancecake.com/community

At a certain point in your freelance career, the question stops being “How do I get more clients?” and starts being “How do I build a business I actually want to keep running?”

In this episode, Austin sits down with Matthew Fenton, a positioning and strategy consultant with nearly three decades of freelance experience. Matthew has worked with brands you’ve heard of, launched White Mystery Airheads, hired agencies and independents from both sides of the desk, and built a long freelance career around a simple but weighty principle: Life plan first. Business plan second.

That idea shapes everything.

Austin and Matthew talk about what it means to design your freelance business around the life you want, not the other way around. They get into the challenges that don’t get enough airtime, like isolation, self-management, and the discipline required when nobody else is building structure for you.

Matthew also shares one of the most useful concepts in the episode: your "gig floor." That’s the minimum threshold a project has to clear before it earns a yes. Right money. Right people. Right kind of work.

They also dig into what actually makes a freelancer rehirable. Spoiler: it’s not just talent. Matthew makes a strong case for reliability, sound judgment, clear communication, and the ability to be a real partner instead of a prima donna with a nice portfolio.

And yes, they also open a delightful can of worms on why freelancing is not for everybody and why Matthew opted out of the whole personal branding conversation years ago.

This is a grounded, honest conversation about sustainability, selectivity, and building a freelance business with enough structure and sanity to last.

Key Points

• A freelance career can be built for longevity. Matthew has been freelancing since 1997 and has sustained his business by staying focused on strategy, positioning, and meaningful client work.
• Life plan first, business plan second. The business should support your life, not consume it. That principle gets more important, not less, as your opportunities increase.
• Isolation is one of freelancing’s hidden costs. Leaving a full-time role means losing built-in social structure and accountability. You have to rebuild those on purpose.
• Warm reconnection beats cold networking. Matthew doesn’t think in terms of “keeping his network warm.” He reconnects with people he genuinely enjoys, and sometimes work falls out of that.
• Your gig floor matters. Experienced freelancers need a minimum threshold for what counts as a worthwhile opportunity, especially when demand is high.
• Reliability beats raw talent. The freelancers who get rehired are the ones who hit deadlines, communicate well, receive feedback, bring perspective, and don’t make the client regret saying yes.
• Freelancing isn’t for everyone. Some people are better off with a paycheck job, and there’s no shame in that.
• Personal branding is optional. Matthew argues that people are not brands and that many of the ideas lumped under personal branding are better explained elsewhere.

Notable Quotes

• “Life plan first, business plan second.”
• “The primary reason for your business to exist is to meet your needs.”
• “A deadline is a promise and failure to hit that deadline is a broken promise.”
• “Some people are truly better off with a paycheck job, and there’s absolutely no shame in that.”
• “I think pretty much the entire field of personal branding is nonsense.”

Resources Mentioned

• Follow Matthew on LinkedIn: https://www.linkedin.com/in/matthewfenton/ (Let him know you found him through this episode!)
• Check out his website: https://matthew-fenton.com/
• Check out Winning Solo: https://winningsolo.com/