How to make life-changing decisions and not regret them

Your 4,000 jars

The average life gives you about 4,000 weeks - 4,000 jars on a conveyor belt, each passing once and never returning. Some are already gone. The rest are slipping past whether you act or not.

When faced with life-changing decisions - career moves, relationships, where to live, what to pursue - many people freeze. They wait for certainty. But while you hesitate, the jars keep moving. The risk is not that you make the wrong decision. The real risk is leaving too many jars empty.

Why we stall

We want certainty we will never get.
We fear regret more than failure.
We drown in options and postpone commitment.

This is existential overwhelm - the sense that you will never do all the things worth doing. If you try to escape it with productivity hacks, you fall into the efficiency trap: the faster you do, the faster new tasks flood in. The jars keep piling up, never filling.

The way out is not more efficiency. It is better choices. And the way to make better choices is to accept finiteness.

Step 1: Accept uncertainty as the baseline

Every big decision is made in fog. You cannot know how your future self will feel or what the world will look like in ten years. Stop waiting for certainty. Start deciding inside the fog.

Jar test: If I only had 500 jars left, would I want to keep spending them this way.

Step 2: Use the 10-10-10 lens

10 days: How will I feel about this choice soon.
10 months: Will the discomfort fade or deepen.
10 years: Which outcome will I regret more.

Thinking in decades reframes jars not as weeks, but as entire shelves. It makes the cost of delay obvious.

Step 3: Reversible or irreversible

Most decisions are two-way doors. If you do not like what is on the other side, you can step back. Only a few are true one-way doors.

Ask: Is this jar gone forever if I choose wrongly. If not, move fast. If yes, take care. Do not treat every jar as irreversible.

Step 4: Anchor to your closed list

Your open list will always be infinite - the quarry full of rocks you could chip at. But your closed list must be three to five priorities.

Question: Does this belong in my closed list. If yes, act. If not, let the jar pass without guilt.

Step 5: Reframe regret

Most people do not regret wrong turns. They regret jars they let pass untouched.

Regret lens: Which choice would I regret not trying before my jars run out. That is usually the growth choice.

Step 6: Adopt good-enough thresholds

Perfectionism wastes jars. Aim for 70 percent confidence - enough to make a reasoned call, not so much you stall forever.

Define in advance: what is good enough to decide. Research will expand to fill the jar if you let it.

Step 7: Last-time reflections

Last-time test: If this were the last jar I got to spend in this situation, would I choose it. If no, stop paying with your jars and choose differently.

Step 8: Build reflection points

Deciding does not mean never revisiting. Commit to a review in three months or a year. That way, you can adjust without torturing yourself with daily second-guessing. Jars get spent either way - better to course-correct than freeze.

Step 9: Strategic underachievement

To honour the jars that matter, you must neglect some jars deliberately. Decide in advance where you will underperform. Maybe you will accept a messier house, slower email replies, or thinner social commitments - all so you can put your best energy into the jars that define your life.

Step 10: Make one irreversible move

The jars only fill when you act. Book the flight, apply for the course, have the hard conversation. Small irreversible actions create momentum. Once the jar is full, you have moved forward.

Worked example — leaving a safe job for something meaningful

Uncertainty: You will never know if it is right until you try.
10-10-10: In 10 days anxious. In 10 months learning. In 10 years regret wasted jars if you stay.
Reversibility: You can often return to similar work.
Closed list: Is this job in your top three life priorities.
Regret lens: You would regret not trying.
Good-enough: 70 percent sure it is viable.
Last-time: If this were the last jar at this job, would you spend it here. No.
Reflection point: Give it 12 months before re-evaluating.
Strategic underachievement: Accept less financial comfort short term.
Irreversible move: Apply elsewhere.

Suddenly, the decision is no longer unbearable. It is practical.

The takeaway

You do not need certainty to make life-changing choices. You need to respect that your jars are limited. Each week spent in paralysis is a week gone.

The paradox is that when you decide boldly, you fill jars with meaning. You may not choose perfectly, but you will rarely regret acting. What people regret most are the empty jars they never touched.

Teaching Module: Exercises and Prompts

1. Reflection prompt

Write down one decision you have been delaying. Ask yourself:

What is the minimum information I need.
Is it reversible.
How will I feel in 10 days, 10 months, and 10 years.

2. Closed list alignment

Look at your current top three to five priorities. Does this decision align with them, or is it noise.

3. Last-time thought experiment

If this week were your last in your current situation, would you want to repeat it. If not, what would you change first.

4. Strategic underachievement exercise

List three areas of life where you are willing to perform at good enough so you can free jars for the big choice.

5. Action step

Identify one small irreversible move - send an email, schedule a call, file an application - that shifts the decision from idea to action. Do it within the next 24 hours.

6. Calendar check-in

Set a review date - three months, twelve months. Write: Am I moving in the right direction with this choice.

Worked example — choosing a university and course

Jack is deciding between studying Computer Science at University A, Music Technology at University B, or taking a gap year.

Uncertainty: He cannot know how he will feel about the subject in three years or what career paths will open. Waiting for perfect clarity will only burn jars.

10-10-10

In 10 days, he will still feel torn.
In 10 months, he will be immersed in whichever subject he chooses, with new friends and routines.
In 10 years, he will likely regret not exploring the subject that excites him most now, because that choice will shape opportunities and networks.

Reversibility

University courses are not one-way doors. He could switch courses after Year 1 or pursue postgraduate study in a different field. The wrong course is not a wasted jar - it is still a foundation.

Closed list

His top priorities might be: 1) meaningful career, 2) developing expertise he enjoys, 3) living in an environment where he thrives. Which option best serves those.

Regret lens

He asks, which choice would I regret not trying. If deep down he would regret never giving music a real shot, that is a signal. If he would regret closing off computing careers, that is another.

Good-enough threshold

He will never hit 100 percent certainty. But if he has 70 percent clarity that Computer Science aligns with his long-term path, or 70 percent that Music gives him the life experience he wants most, that is enough to decide.

Last-time reflection

If this year were his last, would he want to spend it studying this subject, at this campus. That sharpens the fit question.

Reflection point

He could commit now, then promise himself a review at the end of Year 1. That lowers the stakes.

Strategic underachievement

He may accept being less than perfect in one area - not being at the top university in rankings - in order to pursue the subject or environment that truly matters.

Irreversible move

Submit the UCAS application with a first-choice course. That single act breaks paralysis.

The decision shifts from an impossible forever choice to a practical step anchored in his current values, with built-in flexibility.