The Season Before the Leap

There’s a pattern I’ve noticed in almost every business that makes it through a genuine rough patch. It doesn’t show up on a spreadsheet or in a quarterly review. It shows up in the moments just before things turn — when most people would have stepped back and waited.

The hard season doesn’t announce itself as preparation. It just feels like pressure.

I’ve had stretches in my own work where the effort seemed disproportionate to the outcome. Clients weren’t growing as fast as I’d hoped. The pipeline felt thin. Tools I’d invested time in weren’t paying off yet. That combination — sustained effort, visible slowness, creeping doubt — is the exact moment most people quietly pull back and start looking for a simpler path.

But here’s what I’ve come to believe: the difficulty is often the signal, not the obstacle.

Reframing Isn’t Wishful Thinking

There’s an important difference between telling yourself “this will be fine” and actually changing what a challenge means to you. The first is denial. The second is something closer to strategic clarity.

When I hit a difficult period, I’ve started using Copilot in Microsoft 365 not just to triage my inbox or summarise a meeting, but to think through the problem itself. I’ll take a messy situation — a stalled project, a client relationship that feels off-track — and ask Copilot in Teams to reflect it back to me plainly. What’s the actual constraint? What am I not asking? What would this look like from the other side?

When you’re inside a problem, having something surface a different angle can shift your perspective faster than another hour of turning it over yourself. That’s reframing in practice. Not pretending things are easier than they are. Finding the angle you couldn’t see while standing too close to it.

Most People Opt Out Early

The reason hard seasons tend to precede the big leaps isn’t some hidden law of the universe. It’s selection.

When conditions get difficult, people and businesses that don’t have a genuine reason to push through — or haven’t built the habits that carry them when motivation fades — tend to step back. They wait for things to improve before committing again, before investing again, before showing up with full energy again.

That sorting is exactly why the ones who lean in come out with an advantage that simply wasn’t available during easier conditions. The competition thins. The clarity sharpens. Decisions made under real pressure tend to be more durable than the ones made when everything is comfortable.

I use Copilot in Outlook to stay on top of client communication even when my capacity feels stretched — a quick thread summary, a draft response I can refine rather than build from scratch. That keeps me present in conversations I’d otherwise let slip during a hard stretch. Not automation for its own sake. Staying in the game when it would be easy to go quiet.

What You Actually Build

The leap doesn’t come from surviving the difficulty. It comes from what you construct while you’re in it.

The habits, the thinking, the client relationships you kept up, the decisions you made with less certainty than you’d have liked — those compound. They show up later as capability that wasn’t there before, because it couldn’t have been developed any other way.

I don’t look back on the hard stretches as things I got through. I look at them as where most of the real work happened.

If you’re in one of those seasons right now, lean into it. Not because it’s comfortable — it isn’t. But because most people won’t. And that gap is exactly where your next leap begins.

Stop Collecting Tactics. Fix the Three Things That Actually Matter.

I had a coffee recently with an MSP owner who pulled out his phone and showed me his “growth list.” Forty-three items. Webinars, a TikTok plan, a referral scheme, a rebrand, three new service bundles, a partnership he’d been chasing for a year. He was exhausted just reading it to me. And his revenue had barely moved in eighteen months.

I told him I’d happily help him cross off forty of those. Because in my experience, almost every stuck MSP is stuck on the same three things, and the rest is just noise dressed up as activity.

You’re Easy to Overlook

The first problem is that nobody can quickly say what you do or why they’d pick you. Walk into most MSP websites and you’ll find “managed IT solutions for growing businesses.” That sentence could belong to ten thousand others. If a prospect can’t repeat your offer back to a colleague in one breath, you don’t have an offer — you have a category.

This is the part I’d fix first, and it’s the part owners avoid because it forces a decision. Open a blank document and ask Copilot in Word to help you rewrite your core offer five different ways for a specific type of client — say, a 30-seat accounting firm worried about email fraud. Then read each one out loud. The version that sounds like a real person warning a real business is the one you keep. Specific beats clever every single time.

You’re Invisible Because You’re Inconsistent

The second problem isn’t that your marketing is bad. It’s that it shows up once a quarter, when you remember, when things are quiet. Then a big project lands, you go heads-down, and the market forgets you exist. Invisibility isn’t a talent problem. It’s a rhythm problem.

The MSPs who get noticed aren’t louder — they’re just regular. One short, useful thing a week beats a brilliant campaign you run twice a year and abandon. Build the rhythm into the tools you already live in. Draft a month of client-facing tips in a SharePoint document, drop the publishing dates into Planner, and let a scheduled Outlook reminder nudge you every Monday morning. The point isn’t sophistication. It’s that the thing keeps happening whether you feel inspired or not.

Sales Feels Awkward, So You Undercharge

The third one is the quiet killer. Plenty of capable owners walk into a sales conversation, sense the tension when price comes up, and instinctively shave the number to make the discomfort go away. Then they wonder why they’re working flat out and still underpaid.

Awkwardness usually comes from walking in unprepared and hoping to wing it. Before your next prospect call, ask Copilot to pull together what you already know — recent emails with that contact, notes from earlier meetings, the brief from your discovery call — into a one-page summary of what they actually care about. When you walk in knowing their world, you’re not selling. You’re advising. And advisors don’t apologise for their price.

The Real Work Is Subtraction

What struck me about that coffee was how relieved the owner looked when I told him to bin most of the list. We’re trained to believe progress means adding more. With this stuff, it’s almost always the opposite.

Get your offer clear, show up consistently, and stop flinching on price. Do those three, and you can ignore nearly everything else. The forty-three-item list was never the path forward. It was just a very busy way of avoiding the three things that mattered.

The task app you already bought four times

Open most small businesses and you’ll find the same thing. Someone’s running their personal to-dos in To Do. The team’s tracking a project on a Planner board. A manager’s got a Trello tab open. And somebody just expensed a Monday.com seat.

Four tools. One job. Nobody can see the whole picture.

Here’s what most people missed. Microsoft quietly folded To Do, the old Planner, Tasks in Teams and Project for the web into a single app — and just called it Planner. One place. No new licence.

That’s not a rebrand. That’s four subscriptions your clients can stop paying for.

And if they’re on a Microsoft 365 Business plan, they already own it.

What is the new Planner, really?

Think of it as one task list that finally spans the messy middle between “remind me to call the accountant” and “ship the office move by March”.

At the bottom sits your personal stuff — the same tasks that used to live in To Do, now showing up under My Tasks and My Day. In the middle are shared plans your team works from together. At the top, if you ever need it, full project scheduling with timelines and dependencies.

Same app. You just go as deep as the job needs.

Here’s the real win for an SMB. The thing you were about to buy Asana for? It’s the middle tier, and it’s already switched on.

Step-by-Step: putting tasks where the work happens

The mistake is opening Planner as its own app and treating it like another silo. Don’t. Put it where the team already talks.

Find the app

In Microsoft Teams, click Apps on the left rail, search for Planner, and add it. Until April 2024 this was the clunkily-named “Tasks by Planner and To Do” — same app, now just Planner. You’ll also find it on the web at planner.cloud.microsoft if you want it in its own tab.

Pin it to a channel

This is the step that changes everything. Open the channel where the team already works — say your client’s Marketing channel — click the + at the top, and add a Planner tab.

Now the plan lives inside the conversation. No app-switching. No “where’s that board again”. The tasks sit right next to the chat about them.

Build the plan

Create a plan, add a few buckets — To Do, Doing, Done works fine — and start dropping in tasks. Assign people, set due dates, done.

Know which tier you’re on

This is where people get nervous about cost. They shouldn’t. Here’s the line:

Included with Microsoft 365:  Grid, Board, Schedule, Charts
Needs a paid Planner plan:    Timeline, People, Goals, dependencies, sprints

Notice what’s missing? There’s no licence to buy for the everyday stuff. Boards, grids, a schedule view and basic charts are all in the box. You only pay if a client genuinely needs Gantt charts and dependencies — and most never will. The admin documentation spells out exactly what sits where.

Why this actually changes behaviour

“Which app has the project in it again?”

When that question disappears, something shifts.

Tasks stop being scattered across four tools and start living in one place the team already opens fifty times a day. Your personal to-dos, your team’s plans, even your old Project schedules — one pane.

For an MSP, this is a quietly brilliant client conversation. You’re not selling anything new. You’re showing them they’ve been paying a third party for something Microsoft already bundles. That builds trust faster than any upsell ever will.

And the migration worry? There isn’t much of one. Your old Planner boards are already there. To Do items flow in on their own. Project for the web has been retired straight into Planner. You’re not moving anything — it already moved.

If you’re rolling out Microsoft 365 and you’re not showing clients this, you’re leaving them to pay for Trello out of habit.

The new Planner isn’t there to give your clients another task app. It’s there to let them close the other three.

Advance — Use It to Upgrade Your Actual Life

There’s a line I keep repeating. If you’re not reaching for AI every working hour of every day, you’re leaving a silly amount of productivity on the floor. That’s not a pep talk. That’s the baseline now.

But the bit I don’t say loudly enough — the part that actually matters — is this: work is the shallow end. The real compounding doesn’t happen in your quarterly numbers. It happens in the life you build around them.

The job isn’t using it at work

Most people I talk to are still framing AI as a work tool. A faster way to write an email. A quicker way to build a deck in PowerPoint. A cleaner summary of yesterday’s Teams meeting. All useful. All, honestly, the least interesting thing it can do for you.

The long game is personal. You have been handed, for the price of a monthly subscription, a patient thinking partner who will sit with you on any problem, any time of day or night — no ego, no judgement, no billable hour. Whether that’s a Saturday morning over coffee or the drive home after a rough day. Most of my team haven’t really used it that way yet. Honestly, neither had I, until recently.

Every friction point is now a prompt

Think about the things you’ve been avoiding for weeks. They tend to share a shape. A hard conversation with a business partner. A decision about whether to move the family interstate. A contract for a property that you don’t fully understand and don’t want to ask your agent about in front of the vendor.

Every one of those is now a prompt.

Last month I dropped a forty-page purchase agreement into Copilot and asked it to surface everything that wasn’t in my favour. It took about ninety seconds. I walked into the next conversation with three questions I would never have thought to ask, and one clause I’d been about to sign away without a second look. The deal shifted. That moment — that shift — is what I’m talking about.

The conversation you’ve been dreading? Open Copilot in Word, write out what you want to say, and have it stress-test the tone, the gaps, the places you’re being unfair or being walked on. Weighing a big life decision? Give it your situation, the options and what you actually care about, and let it play devil’s advocate until you can hear your own thinking more clearly. Piles of messy personal documents sitting in OneDrive? Point Copilot at them and start asking.

Disrupt yourself first

The job of a good CEO is to look eighteen months down the track and protect the business from whatever’s coming. Most of us accept that as obvious for the companies we run.

Almost none of us apply it to our own lives.

Your job, right now, as a human being, is exactly the same. Look eighteen months ahead. Ask what’s going to be true then about how work, relationships, careers and decisions get made. Then disrupt yourself before the world does it for you — because the world absolutely will.

The people who quietly pick this up — who use Copilot not just for their inbox but for the harder, more personal stuff — are going to look up somewhere in 2027 and realise they’re living a noticeably different life. Not because AI saved them a few minutes on email. Because they used it to think better, decide better, and act earlier than the people around them.

Absorb. Assemble. Align. Advance.

Start today.

Absorb — You Can’t Use What You Don’t Know

The other day, a business owner told me he’d “heard” that AI could now write emails. He said it like it was news. That capability has been sitting on his desktop for well over two years. He wasn’t behind because he lacked tools. He was behind because he didn’t know what was already available to him, inside software he was paying for every month.

This is the quiet problem with AI right now. The technology is moving faster than most people’s awareness of it. The models shipping today can do things that would have sounded like science fiction six months ago. But if your mental picture of AI was formed from a dinner-party conversation eighteen months back, you’re trying to build on a map that no longer matches the territory.

You can’t use what you don’t know exists.

Second-hand AI is a losing game

Most people I talk to get their AI news the same way they get most news — accidentally. A friend mentions something at a barbecue. Their teenager shows them a clip. The barber has an opinion between the scissors and the mirror. By the time a capability filters through that chain, it has been misunderstood, exaggerated, or it has already been replaced by something newer.

That gap between what AI can actually do today and what you think it can do is not a small thing. It’s the entire opportunity. The people who will get real leverage out of AI in the next twelve months are not the ones with the biggest budgets or the fanciest titles. They’re the ones with the clearest, most current picture of what’s possible right now.

The good news is that closing the gap doesn’t require a course, a certification, or a consultant. It requires a habit. And the habit hides inside something you’re probably already doing too much of — scrolling.

Use your feed to feed your mind

The same social platforms that eat your attention can be quietly retrained to deliver a daily education. Two tactics I recommend to anyone who asks.

Schedule it. Open YouTube and search “AI + [your industry].” Subscribe to the top three channels that come up. Then put a twenty-minute block in your calendar called AI Absorb Time. Treat it like a meeting you cannot cancel, because that’s exactly what it is — a standing appointment with the thing that is going to reshape your work. Twenty minutes a day is a hundred minutes a week. Inside a month, you’ll know more about what’s actually shipping than ninety percent of the people in your industry.

Hack the algorithm. Find the strongest AI videos in your niche and drop “FYP” in the comments. It stands for For You Page. Engaging with those videos tells the recommendation engine what you want more of. Do it for a week and your feed quietly rewires itself into an online university, delivered free, on your phone, in the margins of your day. You are paying for social media with your attention anyway. You might as well buy something useful with it.

The habit is the edge

AI literacy is not a one-time event. It’s a drip. The people who stay current are not smarter than everyone else — they’re just in the flow. They’ve built a small, boring habit of absorbing what’s new, and it compounds quietly in the background of their week.

Before you automate anything, build anything, or spend anything, do this first. Know what’s actually possible this week. That is where every real AI decision starts.

Getting Defender for Endpoint onto Windows without the headaches

Most of the MSPs I talk to already have Microsoft Defender for Endpoint sitting in their licensing stack. Plenty of them haven’t actually rolled it out to a single device. That gap between “we own it” and “it’s protecting the fleet” is where I see real risk hiding, and it’s the gap I want to help you close today. Here’s the path I walk through when I’m onboarding Windows machines into MDE, from licensing right through to the bit everyone skips — tuning.

Get the prerequisites right first

Before you touch a single endpoint, check the licensing. Defender for Endpoint Plan 1 ships with Microsoft 365 Business Premium and is fine for most SMBs. Plan 2 sits inside the E5 stack and is what you want if you need full EDR, threat hunting, and automated investigation. Don’t assume — open the Microsoft 365 admin centre and confirm what’s actually assigned.

Next, head to security.microsoft.com and run the initial setup wizard. Pick your data storage region, set your retention (180 days is fine), and turn on preview features so you see new capabilities as they land. Confirm the tenant is connected to Intune as your MDM authority, because that’s the path I recommend for almost every Windows fleet.

Choose your onboarding path

There are three doors into MDE for Windows, and the right one depends on how the device is managed.

Intune (my default). In the Microsoft Defender portal, go to Settings, Endpoints, Onboarding, choose Windows 10 and 11, and pick “Mobile Device Management / Microsoft Intune.” Click the link through to Intune and you’ll land on the EDR policy page. Create a profile, assign it to your “All Devices” or pilot group, and that’s the heavy lifting done. Devices check in on their next sync — usually within an hour.

Group Policy (for on-prem AD environments). Download the onboarding script and the matching ADMX templates from the same Onboarding page. Drop the script into a startup GPO targeting your machine OU, import the templates into your central store, then enable the Defender ATP policies under Computer Configuration. It’s old-school but rock solid.

Local script (pilots and one-offs). Download the .cmd file, run it as administrator on the target machine, and you’re done in under a minute. I use this when I want to prove the pipeline works before scaling.

Verify and then tune

Don’t trust the green tick — verify it. On the device, run the detection test command from Microsoft’s docs. Within fifteen minutes the device should appear in the Defender portal’s Device Inventory with an “Onboarded” sensor status and an active risk level.

Tuning is where most rollouts stall. Push attack surface reduction rules in audit mode first via Intune’s Endpoint Security blade, leave them there for a fortnight, then flip the noisy ones to block and exclude the genuine false positives. Turn on tamper protection, web content filtering, and network protection. Set up email notifications for high-severity alerts so the SOC inbox doesn’t become the place alerts go to die.

This is also where Copilot for Security earns its keep. I’ll ask Copilot in the Defender portal to summarise an incident, walk the kill chain, or draft the client-facing notification, and a forty-minute writeup becomes a ten-minute review.

The bit nobody talks about

MDE deployment isn’t a project, it’s a posture. The clients who get value are the ones whose MSP looks at the Secure Score in the Defender portal every fortnight, treats the recommendations as a backlog inside Planner, and reports progress to the business owner in plain language. Buying the licence is easy. Operating it is the work — and that’s exactly where you justify your fee.

Purpose Is Not a Strategy (And MSPs Are Paying the Price)

You didn’t start your MSP just to make money.

There was something more. A problem you wanted to solve. A frustration you saw in the market. A sense that “IT could be done better” for small businesses that kept being ignored or overcharged.

That purpose matters. It still does.

But here’s the uncomfortable truth many MSP owners don’t like admitting:

Purpose without a plan is just a story you tell yourself.

I see plenty of MSPs who care deeply about their clients, their staff, and “doing the right thing”… yet wonder why growth has stalled, margins are thin, and every year feels harder than the last.

Caring is not the problem. Lack of focus is.

When Good Intentions Don’t Move the Needle

Most MSPs I talk to aren’t lazy or incompetent. They’re overloaded.

They’re saying yes to every request, every new tool, every vendor promise, and every “quick opportunity” that pops up. Slowly, almost invisibly, their original purpose gets diluted by noise.

Here’s what that looks like in the real world:

Offering ten different service bundles because “every client is different”
Chasing the latest security product while last year’s one is barely implemented
Talking about standardisation, but never enforcing it
Claiming to be “strategic” while the business runs on reactive tickets

None of this is malicious. It’s what happens when there’s no clear plan anchoring decisions.

You care about security, but do you have a defined baseline every client must meet?

You care about client outcomes, but can you clearly articulate the outcomes you deliver repeatedly?

You care about your team, but is the business designed to support them—or exhaust them?

Focus Is the Real Competitive Advantage

In the SMB market, MSPs don’t win by being everything. They win by being consistent.

The MSPs making real progress right now aren’t necessarily smarter or bigger. They’ve simply decided what matters—and stopped apologising for it.

They draw clear lines:

This is our core stack
These are our minimum standards
This is how we onboard, secure, and support clients
This is what we don’t do

That focus creates momentum.

Technicians know what “done properly” looks like. Clients know what they’re buying. Sales conversations become simpler. Tool sprawl reduces. Security improves because execution improves.

Most importantly, energy stops leaking.

Every “yes” you don’t think through properly costs far more than the revenue it brings in.

Turn Purpose Into Something That Actually Scales

If your MSP purpose is more than a feel‑good origin story, it needs structure.

Ask yourself three hard questions:

What problem do we solve better than most MSPs our size?
What standards are we no longer willing to compromise on—even if it costs us a client?
What would we stop doing next quarter if we truly backed our own strategy?

None of these require new tools. They require leadership decisions.

Purpose is the why.
Planning is the how.
Discipline is the difference.

The Real Takeaway

You can care deeply and still stay stuck.

Progress doesn’t come from passion alone—it comes from choosing fewer things and doing them consistently well.

If your MSP feels busy but fragile, successful but stretched, it’s not because you’ve lost your purpose.

It’s because it’s time to turn that purpose into a plan you’re willing to defend.

Start there. Everything else gets easier once you do.

Breaking the MSP Growth Plateau: Why “Fine” Is Killing Your Business

If you’ve been running a Managed Service Provider (MSP) business for a few years, chances are you’ve hit a growth plateau.

You’re not failing. You’re not panicking. You’ve probably built $50k–$100k in Monthly Recurring Revenue (MRR). Clients are stable. Cashflow is predictable. The business works.

And that’s exactly the problem.

Most MSP growth stalls not because of bad strategy, weak marketing, or the wrong tools — but because the business has reached a level that feels comfortable. Once that happens, growth quietly switches off.

The Real Reason MSPs Stop Growing

This is something I see repeatedly with SMB MSPs: growth doesn’t stop due to lack of opportunity. It stops because of an internal money set point.

Your business expands until it reaches an income level that feels safe, familiar, and “enough”. Then, without realising it, you start protecting that level instead of pushing past it.

New risks feel unnecessary. Big changes feel uncomfortable. And momentum fades.

To break through — whether your goal is $2M, $5M, or $10M in annual MSP revenue — you don’t need another tactic. You need to reset the way you relate to money and growth.

The Three Financial Zones Every MSP Owner Lives In

Almost every MSP owner operates in one of three zones. Identifying yours is the first step to escaping it.

1. The Panic Zone

This is where money is tight. A major client churns. Cashflow gets scary. Stress levels spike.

It’s unpleasant — but effective. Panic forces action. Sales happen. Decisions get made. Progress follows.

2. The Comfort Zone

This is where most MSPs get stuck.

You’re making “enough”. Nothing is on fire. Revenue is steady. The business is fine.

And “fine” is lethal.

There’s no urgency, no pressure, and no reason to do the hard work required to scale. Comfort kills growth faster than failure ever will.

3. The Complacent Zone

Revenue is higher than ever, but the edge is gone. You lose interest. Spending increases. Growth slows because you’ve stopped caring enough to push.

If you’re honest, you already know which zone you’re in.

Strategy #1: Make Money Matter Again

The fastest way to break out of the comfort zone is to make money emotionally relevant again.

Abstract goals like “higher margins” or “more MRR” don’t move behaviour. People do.

Most of us will work harder for others than we will for ourselves.

Instead of setting a generic revenue goal, attach your next six‑week target to someone you care about:

Hit the goal, and your family gets the trip you’ve been talking about.
Miss it, and you have to explain why — face to face.

That emotional leverage creates pressure. Pressure creates momentum.

Strategy #2: Play a New Growth Game

If you’ve crossed $1M and feel bored or flat, that’s not a failure. It means you’ve completed the survival phase of business.

Now you need a new game.

Some that work well for MSPs:

The Team Wealth Game
Shift from “How do I get richer?” to “How do I make my best engineers and account managers financially secure enough that they never want to leave?”

The Business Model Game
Every major income jump I’ve seen follows a change in sales or delivery.
If you’re still running every sales call, QBR, or escalation — your next growth lever is removing yourself from the process.

The Contribution Game
Tie MSP growth to something bigger than profit. For example, funding a specific outcome for every new endpoint onboarded. Meaning creates momentum.

Strategy #3: Write Yourself a Pool

There’s a famous story about John Lennon wanting a swimming pool and saying, “I’ll write us one.” He wrote a hit song to pay for it.

MSP owners can do the same.

Instead of endless grinding, create a short, focused cash campaign tied to a specific goal:

A cybersecurity audit
A compliance sprint
A fixed‑scope project block

Run it hard for a week. Get paid fast. Build energy.

I call this the Payday Playbook — and it works far better than hoping MRR slowly creeps up.

What MSP Owners Should Actually Do Next

If you want to break your MSP growth plateau:

Identify your current zone
Work in six‑week revenue sprints
Attach real emotional stakes to your goals
Get into rooms where your numbers look small

If you’re the smartest person in your peer group, you’re in the wrong room.

MSP growth isn’t about the technology you manage. It’s about the mindset you bring to the machine — and whether you’re willing to move beyond “fine”.