Many leaders say they want to delegate. Far fewer are willing to tolerate what delegation actually looks like in real life.

Because the real test does not come when everything is smooth. It comes when a team member struggles, gets stuck, and tries to put the task back onto your shoulders. That is the moment where many leaders jump in “just this once,” solve the issue themselves, and quietly train the team to bring back problems instead of owning them.

A great owner-leader does something else. They hold the boundary.

Best if softly, politely, but firmly and clearly.

The point of leadership is not just getting tasks done. It is helping people become successful with you and win with you. People become successful by doing, learning, experiencing, and failing. But some people hesitate to experiment. Some would rather hand the problem upward than carry the discomfort of solving it.

That is where leadership becomes multiplication — or fails to.

If every problem comes back to the owner, the business never really scales. The leader stays trapped in the operating wheel from morning to night, doing everyone else’s thinking instead of their own leadership work.

The temptation is understandable. Most leaders genuinely can do some things better, faster, and more skillfully than their team. That is often why they built the business in the first place. But if that becomes the standard response, they stop being an owner and become the most overpaid problem-solver in the company.

A better response often starts with questions.

When someone brings a problem, instead of immediately solving it, ask: What do you think the best solution is? What are three possible options? Which one would you choose? Why? What should you do next to solve it?

At first, this can feel awkward. Even inefficient. The person may get irritated. They may say, “I don’t know.” You may be in a hurry. You may feel that asking questions instead of giving answers is almost ridiculous when the quickest path is obvious.

But this is where leadership discipline matters.

If they truly cannot come up with anything, then yes — offer a few options. Give direction where needed. But keep teaching the pattern: I want you to think first. 

Because when a person solves something on their own, they do not only solve a problem. They become more confident. They feel successful. They take responsibility. And when they take responsibility, they multiply time and effort inside the organization.

That is one of the real powers of leadership: not doing more yourself, but building other people’s ability to carry weight well.

Of course, this becomes harder if you need everyone to like you.

Many leaders want to be good leaders and best friends at the same time. In practice, those are often two different roles. If your main need is to be liked, you will avoid necessary confrontation. You will make friendship-based decisions instead of value-based decisions. You will “let it slide” for someone close to you; or someone who is emotionally dominant, and then the whole culture pays for it.

That kind of softness does not stay small. It creates a kind of illness in the organization. Standards drop. And sooner or later, the leader has to spend time and energy “treating” a culture problem they partly created by not holding the line earlier.

A strong leader understands this: you make decisions based on values, standards, and what is the right thing to do — not based on keeping everyone comfortable.

That does not mean being harsh for the sake of it. It means being able to say, in effect: as a person, I care about you. But as a leader, I cannot ignore this. We have certain values and standards we need to hold.

That is harder in the moment, but healthier in the long run.

And it turns out that people usually do not resent this kind of leadership as much as leaders fear. In fact, many people grow under it. Especially if you also do one more thing well: recognize progress.

When people find a good solution, encourage them. When they solve a problem well, acknowledge it. What gets praised tends to repeat. What only gets criticism tends to be avoided. People are far more willing to take responsibility again in places where responsibility is seen and valued.

So one crucial trait of a multiplier leader is the emotional resilience to hold a boundary:

not take back tasks;

to have patience not rescue too early;

to stay steady when someone is frustrated with you and struggling to solve a problem;

to lead from values instead of emotion.

One of the most useful things you can do as a leader is to help your people become the kind of problem-solvers and leaders like you are. And that requires the art and skill of having people own their problems.

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That sounds obvious. Every investor says they analyze, compare, and make logical decisions. But the truth is, the market is emotional, and investors are emotional. Decisions are still often made from fear, greed, or FOMO — even when we tell ourselves they are rational.

That was one of the clearest lessons of 2025.

At several points during the year, it felt like I had missed the real rally. I had already been invested in technology through private companies for some time. In public markets, I held large technology names like Meta and Apple. But when it came to chipmakers, I kept missing the entry. I never found the place where I felt confident buying, and I stayed out.

That created the classic investor discomfort: the feeling that everyone else is moving and you are standing still. The story in your head becomes simple very quickly — I missed it, I’m behind, my portfolio is in the wrong place.

But when the year ended, I looked at the facts instead of the feeling.

I had three startup exits. The Tallinn Stock Exchange had risen quietly, almost invisibly, by around 20%. One of the startup investments had an annualized return of roughly 40%, with more upside if certain KPIs are met. And when I looked more carefully at the US market, another important fact appeared: dollar returns are not the same as euro returns. Once converted from dollars into euros, the US market performance looked very different because the dollar had weakened materially during the year.

So the emotional story was: I missed the rally.

The factual story was: my actual returns and exits were better than I had allowed myself to see.

That gap matters.

Because if I had acted from FOMO, I would have started reshuffling the portfolio in a hurry. I would have “played around” with it just to reduce the emotional discomfort of feeling left behind. But that would have been a different decision, based on a different input. Not facts. Emotion.

And this is where many investor mistakes begin. Not with lack of intelligence, but with the inability to distinguish what is happening in the market from what is happening in your nervous system.

A useful principle from 2025 is this: things are rarely as bad as they feel.

In Estonia, for example, the general investor mood was still quite negative for much of the period. Yet by the end of the year, the economy was already showing signs of improvement. Inflation had eased. Export industry was recovering. Major transactions were still being done. Large foreign investors were still making investments in Estonia. It was not true that all foreign capital had disappeared. Quite a few big deals were completed.

But perception lagged behind reality.

And that works both ways. Sometimes the mood stays negative after conditions have already started improving. At other times, sentiment stays optimistic long after things have started turning weaker underneath. Emotion moves with a delay. Facts move first.

That is why investing demands more than instinct. It demands discipline in how you check your own story.

One simple tip is to write the facts down — on paper or in Excel. Why are you making this investment? What are the actual returns? What assumptions are you using?

Putting facts into a visible form helps reduce the power of fear, greed, and FOMO. It does not remove emotion, but it stops emotion from pretending to be analysis.

The lesson from 2025 was not that intuition is useless. With experience, instinct does matter. But instinct without factual discipline can become expensive quickly.

In investing, emotions often speak first. Facts usually speak more quietly. But in the long run, facts tell the truer story.

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What in my life consistently drains more energy than it gives?
What could be eliminated or simplified here? Energy leaks compound faster than time leaks. What tasks I am doing because i feel “i should” but I dont enjoy them, i dont have time for them? What am i saying no to by still choosing to do these tasks?

2. Alignment with my current season

Complexity often comes from living multiple life chapters at once.
What old goals, expectations, or identities can I let go of to make room for what’s next? For example – at this season in our lives, we dont send hand-written Christmas cards. Instead, we try to keep our friends in mind throughout the year. Maybe, when seasons change, we take this up again.
Is this aligned with who I am now? Or is it a leftover from a past identity, goal, or expectation?

3. “If this wasn’t already in my life, would I actively choose it again?”

If the answer isn’t a clear yes, then simplify, reduce, or remove. Its probably a thing of the past lingering.

4. Priorities:

What 20% of habbits and commitments give me 80% of results?
What 20% of people give me 80% of emotional joy?
Protect the essential few. Otherwise they get consumed by the other 80%.

Not “how do I fit more in?” but: “What needs to go so I can get what i want?”

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There’s always something. A kid gets sick. Plans shift last minute. Someone arrives later than planned (hi, that’s me today ). And suddenly the “perfect little break” doesn’t look so perfect anymore.

That’s exactly why we don’t wait for perfect.

Between running multiple businesses, growing a few more, raising three kids, trying to stay healthy, and actually taking care of our relationship — life is full. Busy-full. And if we don’t intentionally create space for each other, it just doesn’t happen.

So here’s our strategy:
 a 2-night getaway every 2 months.
Just the two of us. No kids. No rushing.

Does it always go smoothly? Nope. Sometimes two months pass in a blink. Sometimes plans need adjusting. Today we almost cancelled because logistics went sideways. But we’ve learned that quality time rarely feels urgent — until you realise too much time has passed.

Two months ago we were in Athens. This month we’re in Kärdla. When we leave on Saturday, we already know when the next 2 nights are. That alone changes everything.

We use these breaks to talk, plan, and reset. We look back at what’s happened, and we plan forward. At the end of the year we go through the year month by month (often through photos) and write down the good stuff — because otherwise it’s way too easy to forget how much has actually happened. Then we set goals, make a vision board, and match it with a yearly calendar.

And here’s the non-negotiable part:
Quality time, family time, recovery, sports — those go into the calendar first. Work fills in around that, not the other way around.

We also do weekly check-ins for planning and finances. And we’ve learned that if we want to travel, we need to plan at least half a year ahead — which is why during Christmas we’re already planning summer. School schedules and last-minute bookings are not our friends.

Is this system perfect? Not even close.
It’s messy, adjusted on the go, and sometimes inconvenient.

But it works — because we actually do it.

Imperfect action.
Done on purpose.

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There are excellent files that help with goal-setting. Excellent planning tools, structures. But so you ever find yourself just staring at the file and going blank?

I know some people who dont set goals for that reason. Because when they sit down to “think” about them, nothing shows up. Or there is an inner critic shooting down any idea that tries to show their face. Or what shows up feels like a heavy to do list of all the things “I should be doing”.

Setting great goals is a developed skill. And while people are very different, there are a few common things I have noticed in general about humans, through my coaching clients and also being in the trial/error myself in figuring out a great goal system that supports my growth.

Thinking about goals needs an inspiring environment—something to help get out of the all-controlling cognitive rational mind into the right-brain intuition. Something to get away from the critic. To get access to the visionary.

If you try to set inspiring goals while your nervous system is wired and your brain is in “problem-solving survival mode,” you’ll usually pick goals that are responsible, realistic, and a probably uninspiring.

Here are some ways I get myself into a great goal-setting mode:

1. Calm the nervous system first.

Creative goals don’t come from pressure. They come from safety.

A few quick ways I do this:

– a phoneless walk outside; just observing, deep breaths, engaging my senses
slow stretching with some quiet meditative audio to release tension
– a fast run and possibly some upbeat music when the energy wants to get out and the “doer” inside of me doesnt want to take a seat.
-and my all-time favorite Friday ritual: work-out, slow stretching, long sauna. I call this my “Big picture thinking time”.

2. Movement + record my thoughts.

Movement opens thinking. When I have a trouble getting my thinking going, I walk outside; or drive a car , talk out loud, and record whatever comes. No filtering. Later I either listen back or use an AI transcriber to pull out the gold.
Because sometimes it is not about calming nervous system, sometimes it is also about waking it up. And moving the body is one great way.

3. Change the environment.

This is underrated. Your brain links spaces to modes. Choose inspiring surroundings for inspiring goals.

4. Separate “dreamer” from “critic”.

First I think what I want, whats possible. Then I think about the HOW. Those 2 require different mindset filters and don’t mix well towards great outcomes in goal-setting.

Why go through all this “hassle” to do proper goal-setting?
Because your next year might depend on it.
Specific, inspiring, aligned, and well-thought-through goals will shape your focus and energy and therefore the quality of life you create.

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If your goals die by mid-spring, it’s not necessarily a character issue. I see it way more likely to be a system issue. How to set goals you are actually going to hit?

I love the topic of goals. Because I love to be around people who are alive and motivated, not simply just existing. I strive to be the same way.

There have been times in my life where I set unrealistically big goals, didn’t have the tools to achieve them and missed them; feeling disappointed and tired. There have been times when I set out to be number one and I surprised myself doing it 40% over because I was over-prepared. There have been times when I am simply too tired to even try to plan to hit a goal.

Since December is sharpening-the-tools season before the new year kicks in, I invite you to explore the topic of goals and perhaps challenge you to commit to spending some time with them this month.

Some people say: “Shoot for the stars, at least you’ll land on the moon”? Maybe. But to me that’s more like a vision. Inspiring, but too foggy to guide your real growth. I’m a bigger fan of accountability with myself. I want goals that are clear enough that I can’t wiggle out of them, and specific enough that I can transform them into daily systems and action items to step by step execute on them.

My yearly system is simple:

Three main goals for the year. Why 3?

Because you can achieve anything, but not everything at the same time. Three keeps focus but at the same time it diffuses risk – it doesn’t make all success depend on one single bet.

I like having different ways to win the year, so my three usually hit different areas between health, family, physical environment and work goals.

Not all eggs in one basket. But also not seven baskets you can’t carry.

What is my process of uncovering the 3 most important goals for the year?

1. I brain-dump everything I think I want next year.

2. Then I zoom out into long-term vision (I have a long-term vision carved out for me til I am 120 🙂

3. And ask myself some important questions: If I could only nail one thing, what matters most? What would be one keystone step i want to reach that is a milestone of where I want to end up? Will this happen anyway (not good goal material) — or do I need to create it, prioritise it and actively work on it?

4. narrowing down 3 goals

5. working with those 3 goals to make them failure-proof

6. break them down to weekly controllables ready to be acted upon step by step

So here’s to deciding how you want to spiral up in 2026. To choosing some great goals to put you in the flow.

If you want my planning template for the goals, then I would be happy to share. Feel free to shoot me a message and I will share.

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