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# Why Upskilling Should Not Be an After-Hours Expectation
- URL: https://www.leadingwithempathy.blog/why-upskilling-should-not-be-an-after-hours-expectation/
- Published: 2026-09-15T06:30:21.000Z
- Updated: 2026-09-15T06:30:20.000Z
- Description: If learning matters to the business, it has to be planned like something that matters to the business. Growth cannot live only in evenings and weekends.
- Author: Megan Tipps
- Tags: Leadership, Engineering Leadership, Software Development, Developer Growth, Upskilling, Sustainable Leadership, Team Development, AI Adoption, Work Life Balance, Mentoring, Workplace Culture, Tech Leadership

Learning needs room.

Not just enthusiasm. Not just a link to a course. Not just a cheerful line in a growth plan that says “upskill in this area” and then quietly assumes the actual learning will happen somewhere between dinner, laundry, sleep, family, admin, hobbies, and trying to remember what being a person feels like.

I have been thinking about this for a while, partly because I see it in myself and partly because I see it around me. In tech, we talk a lot about staying relevant. We know the industry moves quickly. Frameworks change, tools shift, AI arrives loudly in the middle of everyone’s existing workload, and suddenly there is another thing we are all meant to understand, evaluate, adopt, question, secure, and use responsibly.

That is part of working in technology. None of us can pretend learning is optional.

But somewhere along the way, we started treating learning as if it belongs outside the workday. As if growth is a personality trait rather than a work activity. As if the people who are serious about their careers will naturally spend their evenings and weekends keeping up, and the people who do not are somehow less committed.

I find that harder to accept now than I might have earlier in my career.

I am not in the early stage of my career anymore, where every new thing feels like a doorway and every late-night rabbit hole feels like proof that I belong here. I still love learning. When something genuinely interests me, my ADHD brain can absolutely decide that this is the topic now, and suddenly I am deep in articles, videos, experiments, notes, side quests, and one very innocent-looking “let me just quickly understand this” that becomes several hours.

But I also have a life outside my laptop. I have hobbies that take me away from the screen. I value rest. I value evenings that are not quietly claimed by the next tool, the next trend, the next urgent professional improvement project. I do not want my whole life to become a background process for staying employable.

That should not be a controversial thing to say.

And yet, in many companies, the expectation is still there. People are encouraged to grow, but no time is created for growth. They are told to keep up, but their delivery load stays the same. They are given learning goals, but no space in the sprint, no protected hours, no mentoring structure, no budget, and no adjustment to the pressure around them. The message becomes strangely contradictory: we value your development, but only if you can fit it into the parts of your life we do not pay for.

I was reminded of this recently in a conversation with one of my mentees. They had been given a growth plan and told to upskill, but they were already overloaded during the day. There was no real room inside the work itself to do the learning. By the time work ended, they were tired from the pressure of the day, which is not exactly the ideal mental state for absorbing new concepts, practising unfamiliar skills, and building confidence.

That kind of situation can look reasonable on paper. A development area has been identified. A person has been told what to improve. A plan technically exists.

But a plan without room is not really a plan. It is just a hope with a deadline attached.

Learning takes attention. It takes repetition. It takes the emotional safety to be a beginner at something again. It takes enough space to be slower for a while, to make mistakes, to ask questions that feel obvious, to try something badly before doing it well. None of that fits neatly into a work culture where every hour is already spoken for and every dip in output feels like a problem.

This is where leadership matters.

I do not think leaders need to bring delivery to a halt so everyone can disappear into study mode. That is not realistic, and most teams would not want that anyway. People still need direction, deadlines, priorities, and momentum. But if learning matters to the business, it has to be planned like something that matters to the business.

That means making time for it inside the workday. It means being honest about the fact that someone learning a new skill may not move at the same speed immediately. It means creating quieter delivery pressure where possible, not because standards are lower, but because growth needs oxygen. It means giving people access to courses, books, conferences, mentoring, workshops, tools, or whatever else is appropriate without making them feel awkward for needing investment.

I have worked in enough places where people were expected to learn on their own dime to know how quickly that starts to feel unfair. It can sound small from a budget line. It does not feel small when the company benefits from the skill, but the individual pays for the course, finds the time, carries the fatigue, and then has to prove the value afterwards.

Mentoring is another part of this that I care about deeply. I mentor now, and I have seen how powerful it can be when someone is not just told to grow, but supported while they do. Sometimes the difference is not a grand intervention. It is having someone help make sense of the next step. It is having space to ask the question you were embarrassed to ask in a bigger meeting. It is hearing, “That is normal, this part is confusing at first,” from someone who has been there before.

Learning becomes easier when people are not left alone with the weight of it.

The AI boom has made this tension even more visible. Across the industry, leaders are encouraging teams to use AI. Sometimes that encouragement is thoughtful and structured. Sometimes it is little more than “go use AI” with no clear guardrails, no shared expectations, no discussion about security or quality, and no practical definition of what good use should look like.

That might work for early adopters. Some people love being let loose with a new tool. They will explore, test, break things, compare approaches, and come back with five opinions before anyone has finished writing the enablement plan.

But not everyone learns that way. Some people need a clearer starting point. Some need examples. Some need boundaries. Some need permission to try without being judged for not instantly understanding how this changes their workflow. Some need leaders to remember that adoption is not the same as announcement.

When leaders forget that, they push people into the deep end and call it empowerment.

Real empowerment has more structure than that. It does not mean controlling every step. It means giving people enough clarity and support that they can build their own judgement. It means saying, “Here is what we are learning, here is why it matters, here is how we will make time, here is what good looks like, here is where you can ask for help, and here is what we are not doing yet.”

That kind of leadership takes effort. It also takes courage, because sometimes making room for learning means pushing back. It means having the difficult conversation with the company when every available hour has already been swallowed by delivery. It means fighting the good fight for your team’s growth before the absence of growth becomes a retention problem, a quality problem, or a burnout problem.

It is easy to say that people are a company’s greatest asset. It is harder to build schedules, budgets, expectations, and team habits that prove it.

There is also a quiet emotional layer to all of this. When learning is only ever squeezed into personal time, it changes how people relate to it. Something that could have felt energising starts to feel like debt. A course becomes another obligation. A new framework becomes another reminder that you are behind. A growth plan becomes less like support and more like pressure dressed in professional language.

People do not learn well when they already feel like they are failing.

They learn better when the environment says, “This matters, and we have made room for it.” They learn better when rest is not treated as a lack of ambition. They learn better when curiosity is allowed to exist without being constantly harvested for productivity. They learn better when they are not forced to choose between career growth and having an actual evening.

For individuals, I think there is relief in naming that. If you are tired after work and do not want to spend your whole weekend learning another tech thing, that does not mean you are lazy. It does not mean you are falling behind as a person. It may simply mean your workday has already used the attention, patience, and energy that learning requires.

Rest is not the enemy of growth. Often, it is what makes growth possible.

For leaders, the nudge is practical. If you want people to grow, design learning into the work. Do not leave it as a private burden and then wonder why only the already-energised, already-supported, already-unburdened people seem to progress. Look at the workload. Look at the calendar. Look at the pressure around delivery. Look at the budget. Look at whether mentoring exists in a real way or only as a nice idea.

Then make room.

Not endless room. Not performative room. Just honest, intentional space where learning is treated as part of the job rather than proof that someone is willing to give more of themselves after the job is done.

Because staying relevant should not require people to slowly hand over their evenings.

And learning, if we truly value it, needs more than encouragement. It needs time, support, permission, and leadership willing to protect the space where growth can actually happen.

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