Your Small Business Technology Planning Guide for 2026

I was doing dishes last night, thinking about the year ahead.

Not my favorite activity, but there's something about a sink full of dishes that forces you to just think. And I got to thinking about all the technology conversations I've had with clients this past year. The ones that went well. The ones that didn't.

Here's what I noticed: the businesses that felt confident about their technology weren't necessarily spending more money. They just had a clearer picture of what mattered.

January is when most of us start thinking about budgets and plans for the year ahead. And if you're running a small business, technology spending can feel like a black hole. There's always something new, always someone telling you that you need to upgrade this or adopt that. It's exhausting.

So let me share a framework I've been using with clients. Nothing fancy - just a way to organize your thinking.

The Three Buckets

I break technology investments into three categories:

Must-haves are the things that protect your business and keep it running. Solid backups, security basics, reliable infrastructure. If something in this bucket fails, you're in real trouble. These get funded first, every time.

Should-haves are improvements that make your team more efficient or replace systems that are costing you more to maintain than they're worth. That old phone system you're paying too much for. The server in the closet that's been there since 2018. Software subscriptions you forgot you're even paying for. These deserve attention when the must-haves are covered.

Nice-to-haves are the shiny objects. AI tools, automation experiments, the latest thing everyone's talking about. Not saying these are bad - some of them are genuinely useful. But they shouldn't come before the first two buckets.

Questions Worth Asking

Before you spend a dollar on technology this year, ask yourself:

Which bucket does this fall into? Be honest.

What happens if I don't do this? Sometimes the answer is "nothing much." That's good information.

What's the actual cost of the problem I'm solving? Not just dollars - time, frustration, risk. Sometimes a problem that seems small is actually eating hours every week.

Is this fixing a symptom or the root cause? I've seen plenty of businesses buy new tools to work around problems that should have been fixed differently.

A Few Warning Signs

You might be due for some technology attention if:

- Your team has developed workarounds for things that should just work

- You're paying for systems nobody uses anymore

- The phrase "it's always been like this" comes up a lot

- Your IT setup would be hard to explain to someone new

None of these are emergencies. But they're worth noticing.

What This Means for You

I'm not trying to sell you anything here. Honestly, the best outcome is that you read this, think through your situation, and feel more confident about the decisions you're already making.

But if you'd like to talk through your technology priorities for the year, I'm happy to do that. Sometimes it helps to have someone ask the questions you haven't thought to ask yourself. Just reply to this email and we'll find a time.

Here's to a good 2026.