The lone wolf roams the plains – majestic, free, answering to no one. But here’s the catch: if that wolf doesn’t capture his dinner, he starves to death.
Compare that to the house-kept dog. Food appears in the bowl every day like clockwork. A warm bed, predictable routine, and veterinary care are included. The only tradeoff? Can’t go outside without a leash.
This captures the consulting reality perfectly. Everyone sees the freedom and independence – work from anywhere, choose your clients, set your rates. What they don’t see is the constant hunting required to survive. There’s no 401k matching, no free snacks in the breakroom, and no one else responsible for keeping you fed.
I’m not trying to scare you away from independent consulting. I’ve been at it for almost six years now, and I wouldn’t trade the growth it has forced on me for anything. (That said, I reserve the right to put a collar and leash back on at any time in the future.) But if you’re thinking about making the leap, or you’ve already made it and are struggling, this post is about survival tactics – not just the romance of independence.
The Two Questions I Always Get Asked
I have this conversation at least once a week. Someone reaches out who’s either thinking about going independent or who’s already made the jump but is struggling to get traction. After almost six years at this, I’ve also become the person people in my network send their colleagues to when someone leaves their job (or gets fired) and announces they’re going to “try consulting” but has no idea where to start. The questions are always the same:
“How do I get clients?” (The hunting problem)
“How did you pick something so specific?” (The positioning problem)
Most people think these are separate issues. They’re not. They’re interconnected parts of the same challenge, and solving one without the other is like trying to clap with one hand.
I’m almost six years into this journey. I can’t say I have everything figured out, but I’ve accumulated a lot of knowledge about what doesn’t work. And sometimes that’s more valuable than success stories.
Part 1: What NOT to Do
Let me save you some pain by sharing the approaches that seem obvious when starting out but turn out to be traps. Other people might make these work – they’re just not the norm for me, and definitely not the silver bullets you think they’ll be. I certainly couldn’t crack the code on any of them.
Talent Marketplaces: Why Catalant, TopTal, etc. are challenging
When I started, I thought I’d just join these talent marketplaces, and projects would flow my way. TopTal, Catalant, all those platforms that promise to connect you with high-paying consulting gigs.
Here’s the reality: these platforms are brutal. You’re competing with a massive oversupply of talent, often with significant pricing pressure.
Even if you win projects, you’re positioned as a commodity. The platform sets the terms, takes their cut, and you have zero differentiation from the thousands of other “product management consultants” or whatever your category is.
Can they work as gap-fillers for cash flow? Sure. But they don’t scale as sustainable business models, and you’re always at risk of the platform changing their algorithm or terms.
The Early-Stage Company Trap: Why sub-$5M ARR companies are dangerous
This one’s tempting because so many early-stage companies clearly need help. They have obvious problems, enthusiastic founders, and compelling visions.
The problem? Lots of need, zero ability to pay. You become an accidental equity-compensated VC, taking on vast amounts of risk for uncertain payouts. Even if the company succeeds, your equity slice is usually negligible.
Unless you’re independently wealthy and consulting for fun, avoid the sub-$5M ARR trap.
The Execution vs. Business Development Reality
Here’s something no one tells you: you can’t just “turn on” business development between projects. I see people make this mistake constantly – they get busy with client work, stop all business development activities, and then suddenly they’re scrambling when the project ends.
You must build margin into your business model to support continuous sales activities. Whether that’s 25% of your time or a percentage of your revenue, you need to budget because you’re now running a business, not just delivering client work.
This is where pricing becomes critical. Your rates need to cover not just your time, but the time you spend hunting for the next meal.
Part 2: The Three Resources That Could Have Saved Me Years
Here’s what I wish someone had handed me on day one. After burning through multiple positioning attempts and countless hours of trial and error, I finally discovered the resources that actually move the needle. These aren’t affiliate links or recommendations I’m getting paid for – they’re just the best tools I’ve found.
1. David A. Fields – The Irresistible Consultant’s Guide to Winning Clients
This book is probably the best $10 I’ve ever spent. David covers everything from niche selection to client conversations, and he has systematic approaches for discovering your positioning instead of just guessing.
Here’s what I learned the hard way: reading the book isn’t enough. I attended his Solo Practice Accelerator workshop and then hired David as a coach for an extended period because I needed someone to beat me into submission on focusing. Sometimes you need an external person to make you stick with the hard work of positioning instead of jumping to the next shiny object.
2. Umbrex/Veritux Network (umbrex.com)
This is a free network of independent consultants founded by Will Bachman, an ex-McKinsey guy who went independent back in 2008. Will basically realized he had all the same questions you’re probably having right now, and there was nothing out there to help.
They put on weekly webinars covering everything – how to set up a CRM, what contracts to use, how to negotiate with procurement, whether you need a virtual assistant. All the blocking and tackling of running a consulting business.
They also have mastermind opportunities where you can connect with other consultants working through similar challenges. I’m part of a group of about 10 solo and boutique consultants who meet monthly to share best practices.
3. Unleashed Podcast + Essentials Guide (umbrex.com/unleashed-essentials)
Will also hosts a podcast called Unleashed with over 600 episodes. But here’s the key – they’ve categorized the essential episodes by topic area. So if you’re wondering about business development, LinkedIn optimization, or setting up operations, you can go straight to the relevant episodes instead of wandering through hundreds of conversations.
This saved me months of trial and error on basic business setup questions.
I’ll also mention The Freelancer’s Bible as a bonus resource. It covers a lot of the fundamental business setup details that are common across consulting and freelancing – things like contracts, taxes, and operational basics that you’ll need regardless of your specific niche.
Part 3: My Personal Journey (The Learning Process)
Now let me tell you how I learned all this the hard way.
I left my last full-time job, did a year-and-a-half sabbatical traveling around the world, and came back thinking I might start a product company. But I didn’t have a product idea, so I figured I’d try consulting temporarily and maybe stumble across a problem worth building a company around.
I’m still consulting almost six years later, so that tells you something about my product instincts.
What I didn’t expect was how hard it would be to figure out what kind of consultant to be. Coming from a product management background, I thought I knew what I was good at. Turns out, being good at something and being able to market it as a consulting service are completely different skills.
The Positioning Traps I Fell Into
The Fractional Anything Trap: Why “Fractional CPO” was a terrible idea
Coming from a product management background, I thought “fractional Chief Product Officer” was brilliant. I’d seen fractional CMOs and CFOs, but no fractional CPOs. This is either a huge opportunity or a terrible idea, I thought.
It was a terrible idea.
Here’s why: in CPG companies, brand is the most valuable asset, so you have brand managers. In technology companies, the product is the most valuable asset. It’s very difficult to pitch an outsider helping you with the most valuable asset in your company. You want an internal person doing that.
There’s also the measurement problem. How do you judge a fractional CPO’s success? Sales reps have quotas, marketing has MQLs, and engineers have sprint points. But product success is squishier and longer-term. As an outsider, it’s nearly impossible to demonstrate clear ROI.
Plus, I discovered that nobody thinks they have a product problem. If growth is slow, it’s because sales can’t sell or marketing can’t market. If delivery is slow, it’s because engineering can’t execute. But the product? The product is fine.
The Retention Pivot: Why early-stage companies + retention consulting didn’t work
After the fractional CPO disaster, I pivoted to customer retention. I was excited about this – retention is clearly important, there’s data to work with, and I could demonstrate ROI.
Problem: Early-stage companies don’t prioritize retention. They’re in growth mode, focused on acquisition. And when companies do care about retention, it’s usually owned by customer success teams, not product.
Here’s the kicker: Customer success teams don’t want to solve retention problems the way a product person would. They don’t want data analysis and root cause identification. They want to hire more people and give customers “more hugs per hour.”
If you want to consult in the retention space, you’re basically selling customer success playbooks and tool implementations, not strategic analysis.
The PLG Problem: Definition hell and positioning quicksand
I also looked at product-led growth, thinking it was a hot area with clear positioning. Wrong again.
PLG has the same problem as product management – everyone has a different definition. You end up spending 20 minutes of every conversation trying to align on what PLG even means before you can start pitching your solution.
That’s not where you want to start a sales conversation.
Finding What Actually Worked
After multiple failures, I finally discovered pricing through David Fields’ systematic approach. It wasn’t some brilliant insight on my part – I literally worked through his frameworks for identifying consultant-friendly problems until something clicked.
But first, I had to understand a fundamental mindset shift. In corporate, being “smart and getting shit done” is often enough to succeed. You get projects assigned to you, you execute well, you get promoted. Your value is measured by your ability to handle whatever gets thrown at you.
Consulting flips this completely. While those qualities are absolutely required for running a consulting business, they’re not enough. Nobody cares how smart you are or how well you execute if you can’t articulate exactly what problem you solve and why it matters to their business. You need to be able to speak to a concrete problem that drives real business results and that people actually care about solving.
This is why so many brilliant corporate executives struggle when they go independent. They’re used to their competence being obvious within an organizational context. But as an outsider, you have to prove your relevance before anyone cares about your competence.
Finding My “Job #4”
David taught me to think about this: full-time employees have their top three priorities that they’re measured on. You can’t compete with those. But there’s always a Job #4 – something they know needs to get done but they don’t have bandwidth for because they’re focused on their core responsibilities.
Pricing fit this pattern perfectly:
- It’s not usually anyone’s full-time responsibility
- If someone has done it before, it was probably years ago
- It’s strategic enough that they don’t want to mess it up
- Companies have short organizational memories on pricing decisions
This gave me a clear value proposition: I’m not trying to replace your product team or take over core business functions. I’m handling the important thing that’s sitting in your backlog because everyone’s too busy with their day jobs.
Discovering Problem-Market Fit Through Market Repetition
You can’t know upfront which companies actually have your problem or are willing to pay to solve it. I discovered my ideal client profile through experience, not theory.
Different company stages have different problems and budgets. Early-stage companies might have pricing challenges, but they can’t afford strategic pricing consulting. And the pricing problems are rarely at the top of the c-suite’s “must get done” list – they have other more pressing survival issues. Companies at $20M+ ARR have sophisticated enough businesses that pricing optimization can move the needle significantly.
But I only learned this by doing the work, not by theorizing about it.
Why Having a Coach Was Essential
Going back to David Fields – hiring him as a coach was one of the best investments I made. Not just for the frameworks, but for the accountability.
When you’re doing this alone, it’s easy to get discouraged and jump to the next idea. Having someone beat you into submission on focusing and working through the hard parts of positioning is invaluable.
The Uncomfortable Truth
It took multiple failures to find what worked. This isn’t a story about having brilliant insights upfront. It’s about being willing to fail your way to success and having enough runway to survive the learning process.
Almost six years in, I haven’t starved to death yet, but it’s always evolving. The work never stops.
The Bottom Line: Realistic Expectations
Here’s what I want you to understand: it’s harder than it looks, just like the lone wolf.
You’re trading one set of problems for a different set of problems. In corporate, you might have annoying meetings and bureaucracy. As an independent consultant, you have irregular income and constant business development pressure.
Success requires both expertise AND business development skills. Being good at your craft is table stakes. The real challenge is building a sustainable business around that expertise.
The resources exist to help, but you have to do the work. No one’s going to hand you a consulting business.
But the freedom is real. So is the responsibility for hunting your next meal.
Practical Next Steps
If you’re serious about this path, here’s what I’d recommend:
- Read David’s book first – Don’t skip this step. The frameworks will save you years of wandering.
- Join Umbrex and consume the essentials – Start with the categorized podcast episodes on their essentials page.
- Start thinking about YOUR “Job #4” – What do companies in your area of expertise need but don’t have bandwidth for?
- Start networking hard while you still have a job – Most people with corporate jobs never network, and it’s much harder once you have that “vendor smell” on you than when you have the shiny “VP of Important Stuff at Badass Company X” on your LinkedIn. Leverage that corporate credibility while you have it.
- Stop playing the “I’ve got the newer model car” game with the other corporate drones and start saving for 12-18 months of runway – You need living expenses covered, not just business startup costs. The hunting never stops.
- Be ready to fail your way to success – Your first positioning idea probably won’t work. That’s normal, not a sign you should give up.
The Wolf Pack and the Wild Hunt
The lone wolf life isn’t about being completely isolated. Even wolves sometimes hunt in packs when it serves them. Some of the most successful consultants I know have built networks of trusted partners they can collaborate with on larger projects or refer work to when something’s not in their wheelhouse.
The goal isn’t to be completely isolated. It’s to have the independence to choose your collaborations rather than having them imposed on you.
But whether you’re hunting alone or with others, the fundamental reality never changes: you still need to catch dinner to survive. The freedom is real, the responsibility is yours, and the hunt never ends.