TALLGLASSOFWALTER

Let’s start with a dumb mistake I made in 2024.

I took FMLA to have heart surgery. Not a vacation. Not a side hustle break or sabbatical as an excuse to finally get some steps in. Actual, chest open, learn-to-breath-again heart surgery.

The boutique agency I was with at the time took this surgery very personally. When I came back?
My role was gone.
My department was gone.
My duties had been “downsized” and just like that, poof!
I was displaced. My four-year plan, gone. Kind of like the medical waste from my surgery.

Personally, I don’t believe in litigation. I believe in doing good and treating people with kindness as its own reward, mostly.

This is not the right mindset to go into consulting with.

Good intentions are simply that – good intentions. They don’t trasnfer to your bank account.

I walked into that same rake a few more times across four engagements in 2025 and 2026. A commercial baking periodical, a construction firm, a SaaS company specializing in inventory, and even a nonprofit undergoing an organizational restructure all reinforced the same lessons.

I found each opportunity the old-fashioned way: prospecting, canvassing businesses with open positions, reading desperate LinkedIn pleas, calling in favors from peers. It seemed like cosmic timing as everyone was crying out for content strategy. Consulting felt like a redirection more than a layoff.

So I showed up with kindness. I met with senior leadership. One company even brought me in to do a workshop at a leadership summit to help reframe their organization and production teams. I thought I was being helpful, and I thought if I just showed them what was possible, my value would speak for itself.

Here’s what actually happens when you give someone the recipe: they assume they can make the meal themselves.

What I’d do differently (& what you should steal for yourself):

First things first, sign the dotted lines at the beginning. Not after. I reacted with NDAs, contracts, and SOWs after the discovery work was already done. It’s in those moments when I requested commitment that businesses suddenly lose WiFi connectivity and access to their emails. Every single one.

This means it is up to you to set clear expectations of the output and the product of your engagement. Remember the children’s book If You Give a Mouse a Cookie? As a consultant, your expertise is that cookie. If you give one product away for free, the rest will be given a similar value.

Remember also, even if something feels like second nature to you, that industry intel is valuable. Seek compensation. Don’t apologize for it.

My hot, controversial take (which I cannot emphasize enough): avoid small, “culture-first” engagements. Every single one of these organizations starts by trying to ingratiate you with a family culture.
The boutique agency that laid me off after surgery, “Put people first.”
The canary in the coal mine to each of these failed engagements was the same song and dance.
The most toxic engagements will almost always refer to their employees as their “tribe” while making no concerted efforts toward diversity, equity, inclusion, or belonging.
For me, at least, the pattern will repeat until you stop ignoring it. Don’t.

Finally, I got into those C-suite meetings with little more than gumption and good public speaking. Confidence and certainty in your abilities open many doors. That part always seems to work.

My fellow consultants (& general humans), your intentions don’t always match the person across the conference table.

Here’s the actual cost, so you don’t pay it yourself –

• Commercial baking periodical: four meetings, ten hours of work, an editorial style guide, an activation guide for an annual conference, and an organizational chart.
  • Total hours: 25 | Value of work: $1,875

• Construction firm: multiple meetings, an entire digitization strategy, a communications plan for an employee resource group, two field guides for new hires, plus new content creation.
  • Total hours: 37 | Value of work: $2,775

• SaaS: a full content solution, organizational structure guides streamlining three departments and their content production, plus four weeks with their leadership team.
  • Total hours: 85 | Value of work $6,000

None of it compensated. That’s not pocket change. That is rent, groceries, a safety net, and repayment of hospital bills.

Here’s where I land in 2026…

I reframed my consultancy. Kindness isn’t the problem, but kindness without a contract is little more than a donation of time.

If you’re a consultant, freelancer, fractional employee, or anything in between, and you need a soundboard? I’ve got plenty of failure to help you avoid the same.

I’ve built a network of consultants and professionals to provide peer support, resources, and a witness to predatory business practices. Reach out before donating your time or beating yourself up.

& to the boutique agency that laid me off after surgery, the commercial baking periodical still struggling to outpace your competitor, the construction firm using my intellectual property, and the SaaS touting your “tribe”…
Integrity always shows up in action; seldom is it proven in words.

Keep going. I sure will, and I’ll see you out there. Good stories make for great times.