I get the message in my inbox almost weekly: “I’m thinking about stepping out of corporate and trying consulting. How did you do it?”
It is an enticing thought. For many people choosing the problems you solve, and avoiding the corporate bureaucracy is genuinely exciting.
Recently, I sat down with Greg McDonald and Geoff Wolinetz on their podcast, Leadership In, for a candid, three-way deep dive into what independent advisory work actually looks like behind the curtain. Greg, Geoff, and I have all built independent practices, and we’ve been comparing notes for a long time.
Here are three core ideas we discussed that every senior operator should consider before making the jump.
1. Consulting Isn’t “Working Less”—It’s Working Differently
One of the most persistent myths is that consulting is a relaxed semi-retirement. Geoff brought up a great point during our conversation: for every hour of client delivery, you are often investing an hour or two in business development, admin, and positioning.
When you go solo, you aren’t just the domain expert; you are the lead generation engine, the legal department, the IT support, and the billing desk. If you are entering this path to cruise, you will quickly find that the “non-billable” half of the equation requires relentless discipline.
2. Specialization Beats Generalism Every Time
The biggest mistake seasoned executives make when launching an advisory practice is saying: “I can help companies with strategy, operations, and growth.”
To a prospective buyer, that means nothing.
To win engagements, you need sharp positioning around specific, high-stakes pain points. My go-to advice—and a tactic we discussed on the episode—is simple: in every industry conversation you have (prospect or peer), ask “What is the single biggest problem keeping your team up at night right now?” Listen closely. Your service offering should directly answer those explicit headaches, not your abstract résumé.
3. Solo Doesn’t Have to Mean Isolated
Building an independent practice doesn’t mean operating in a vacuum. As Greg, Geoff, and I discussed, having a trusted peer network—a loose “co-op” of fellow independents—is essential. We share frameworks, pass relevant inbound leads when an ask falls outside our core wheelhouse, and sanity-check proposals. Cultivating those peer relationships early is often what makes the difference between burning out and building a sustainable practice.
4. The AI Double-Edged Sword: Massive Leverage vs. Commoditization
We also dug into how AI is shifting the advisory landscape. On the upside, it acts as a massive force multiplier for a solo practitioner—handling desk research, synthesizing transcripts, and streamlining administrative overhead without needing a junior team.
The flip side? Basic synthesis and generic frameworks are getting commoditized fast. If your value proposition is just pulling together standard industry recaps, AI will eat your lunch. What clients actually pay for today is deep, battle-tested judgment, real-world context, and the ability to navigate complex organizational trade-offs that an LLM simply can’t replicate.
If you are at a career crossroad considering the independent path, or if you simply want an unfiltered look at the trade-offs between predictable corporate structures and advisory freedom, check out the full conversation on Leadership In (or my copy on The Yield Doctor).
A huge thank you to Greg and Geoff for having me on and for creating space for an honest conversation about the craft.
Have you considered taking the leap to independent consulting, or are you running your own practice today? What has been your biggest surprise along the way?
Connect with Geoff Wolinetz on LinkedIn, or follow JPEG Consulting
Connect with Greg MacDonald on LinkedIn, Or follow Chelsea Strategies