What’s Really Blocking You From Upskilling? and How to Get Past It

Let’s be honest. You know things are changing fast. Everyone’s talking about AI, automation, digital transformation. You keep hearing that if you don’t upskill, you’ll get left behind.

And yet… you haven’t done it. Or you’ve tried, stopped, put it off, felt overwhelmed.

That doesn’t make you lazy or unmotivated. It makes you human.

For many women in their 30s and beyond, especially those already in busy careers or running businesses, the barriers to upskilling aren’t always what they seem. It’s not just about time or access. Often, it’s deeper than that.

So before you blame yourself, let’s unpack what might really be in the way, and how you can move through it in a way that feels supportive and doable.

1. You don’t have the time

This is the most obvious one. Between work, family, mental load, and everything else, the idea of adding learning to your list can feel impossible.

But here’s the reframe: upskilling doesn’t have to mean formal courses or five hours a week. It can mean watching a 15-minute session during lunch. It can be asking someone how they’re using a tool and giving it a go for yourself. It’s about finding small, consistent ways to stay connected to what’s changing.

Ask yourself: can I carve out 20 minutes a week? Could I replace one scroll session with something that gives me a spark of clarity?

Start there.

2. You’re afraid of looking stupid

This one doesn’t get talked about enough. Especially if you’ve built up experience and credibility in your career, the idea of being a beginner again can feel uncomfortable. You might worry, what if I can’t keep up? What if I ask the wrong question? What if everyone else already knows?

You are not alone in feeling that. And you are not behind.

The truth is, the people who stay relevant aren’t the ones who already know everything. They’re the ones who are willing to be curious and keep learning. Confidence doesn’t come first. It comes from action, even if it’s messy at the start.

3. You’re comparing yourself to younger people

Let’s say it how it is. Tech and digital spaces often centre younger voices. You might see someone in their 20s launching a new thing, adopting new tools fast, and feel like the moment has passed for you.

But here’s what you’ve got that they don’t: experience, judgment, perspective, and the ability to connect the dots. The combination of lived experience plus digital awareness is powerful. We need more women who understand people, strategy, leadership and context — and who are also willing to use new tools.

It’s not too late. It’s never been a better time to bring those two things together.

4. You’re stuck in perfectionism

If you’ve always been someone who gets things right, takes pride in delivering well, and doesn’t like doing things badly, learning something new might feel hard. Upskilling means letting go of control for a bit. It means getting things wrong, asking for help, and not having polished answers.

That can feel deeply uncomfortable.

But progress doesn’t come from perfection. It comes from action. From having a go, learning one thing, applying it, then building from there. You don’t need to be perfect at the start. You just need to begin.

5. You’re overwhelmed and overloaded

Sometimes it’s not about the skill at all. It’s about the mental load you’re carrying. You’ve got too many tabs open in your head, and the thought of opening one more makes you shut down. That’s real. And valid.

In those moments, it helps to stop trying to do everything and just focus on one thing. One video. One session. One conversation. Your nervous system can’t learn well if it’s in survival mode.

So be gentle. Come back to learning when you feel grounded. And choose formats that meet you where you are — not ones that add more pressure.

6. You don’t have a safe space to learn

One of the biggest reasons women put off upskilling is because they don’t feel safe to try. Especially in fast-paced, male-dominated or overly competitive environments, there’s little room for experimentation or honest questions.

What you need is a space where you can ask anything, try things, and not be judged for not knowing. Somewhere you’re not made to feel behind. A space that gets what it’s like to be learning while managing real life.

That’s exactly why we built Digital Women.

What upskilling actually looks like

It doesn’t have to be a 12-week course. It can look like:

• Attending one live session a month

• Watching a 10-minute replay on your commute

• Asking someone how they’re using a tool and trying it out

• Reading one helpful article a week

• Talking in a space where people are generous with what they know

Upskilling is simply staying open. It’s about saying, I don’t have to know it all, but I am willing to learn.

You don’t need to do it alone

At Digital Women, we know that the biggest shift happens when women feel safe, supported and surrounded by others who get it.

We’re building a platform where you can stay ahead without feeling behind. Where you can ask questions without feeling small. Where you can learn from others who are navigating the same changes and challenges.

It’s not about performance. It’s about progress. It’s a place to learn what matters now — without pressure, perfectionism or pretence.

Final thought

If you’ve been telling yourself you “should” be learning more, and then feeling stuck or guilty when you don’t, stop.

You’re not doing anything wrong.

Start where you are. You’re not behind. You’re not too late. You’re not the only one feeling like this.

And if you’re ready to move forward, we’d love to have you with us.

👉 Apply to join the waitlist: https://www.digitalwomen.club/waitlist