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Education & Work – Story Prompts That Record Your Intellectual Journey

We are not our jobs or our qualifications, but they’re full of great stories and offer insights into our interests, motivations and skills.

Explore these Story Prompts about education and work to track your progress through education and work, preserving memories of how things used to be while providing helpful insights for younger generations.

A boss at work.

Memorable Bosses

What stories do you have about your best and worst bosses?

  • Who were your standout bosses and what made them so special?
  • Do you have any advice for people with less capable bosses?
  • Do you have any advice on how to be a great boss?
A man painting for his work.

Inspiring Jobs

If all jobs paid the same what would you choose to do?

  • Ignoring the practicalities of working hours, travel time and financial responsibilities, is there a job or career path that you would love to undertake?
  • Would you continue with what you currently do?
The work environment, as it used to be.

Working Conditions

What working conditions or financial benefits might surprise future generations?

  • Work environments are constantly changing.
  • Not so long ago, health and safety weren’t seen as important, and offices were very formal.
  • What changes in working conditions have you experienced over your career?
  • What do you miss from the past?
  • What changes are you pleased about?
People learning in a library.

Skills Desired

What professional skills do you want to learn and why?

  • Are you interested in learning a new set of skills for work?
  • Would a change in career path interest you?
  • Why are you interested in learning these skills?
A school exterior.

Education Changes

If you could go back what would you change about your education?

  • What was missing from your education?
  • Do you wish you had chosen different subjects at school?
  • Did you try your hardest at school?
An old image of how children used to work in school.

Changing School Experience

How might your experience at school be different to later generations?

  • Corporal punishment, most typically the use of a cane, was only recently outlawed in the UK in 1998! It’s astounding in some respects how different modern schooling is.
  • What experiences did you have at school that modern students may not experience?
  • What subjects did you take at school?
  • What were your teachers like?
  • How do you see schools evolving in the future? Does an ever-changing world require different skills from school graduates?
A modern school classwork, with the teacher standing at the front.

School Environment

What were your schools like?

  • How was your school set up?
  • What rooms or equipment did you have?
  • Did you have sports opportunities outside?
  • How many people were in your classes?
A boy writing in his school book.

Record Their Progress

As a parent, can you record your child’s school progress with reports or observations?

  • So much about a child’s journey through school risks getting forgotten over time. The final qualification certificates are just a summary of the outcome, not tracking their progress and hard work over the years.
  • Capture photos of your child’s homework and written work in exercise books.
  • Create a digital record of their school projects and the things they drew, built and sculpted.
  • Involve your children in creating stories about their time and school and how they are getting on.
A man in a suit heading to work.

First Jobs

What were your first jobs like?

  • How did it feel going to your first-ever job?
  • Where was it, what did you do and how did you like it?
  • Did you have a lot of smaller jobs, perhaps summer holiday jobs as a student?
  • What advice can you offer to people getting ready for their first job?
  • How is the work environment different from education?
A collage graduate holding her certificate.

Qualifications & Their Impact

What professional qualifications do you have and how have they affected your career?

  • What are your qualifications?
  • Are you pleased with your choice of subjects?
  • Were you pleased with your results when you received them?
  • How important have your qualifications been in your subsequent career and life in general?
  • Have you ever considered getting further qualifications?
Two women being creative at work.

Career Aspirations

What were your career aspirations and have you achieved them?

Childhood Aspirations

What did you want to be growing up and why?

A teenager, ready to hear career advice.

16 Year Old Advice

What career advice would you give your 16-year-old self?

  • Did you feel daunted at the idea of jobs and a career when you were 16?
  • How did you choose your further education and career path?
  • What advice do you think is important for 16-year-olds today?
A professional person working in a surgery.

Proudest Moments

What are you most proud of in your career?

  • It might be your contribution to an important outcome.
  • Or perhaps a time when you stepped outside your comfort zone and did something you didn’t think you could do.
  • How significant were these moments in your career or to you personally?

The Role of Luck

What luck (good or bad) did you have in your career?

  • Have you found yourself landing a job or discovering a career path almost by accident?
  • Were you lucky with the people you worked with? Perhaps they helped your progress or taught you valuable lessons?
  • Were you lucky with timing – being in the right place at the right time, so you could accept an important project or role?
  • Has bad luck played a part in your career? For example, those service industry employees who were hit hard by COVID-19.
Smiling children sat in their classroom.


How would your school classmates describe you?

A school teacher drinking coffee.

School Teachers

How would your school teachers describe your time with them?

  • Do you have any old school reports?
  • Are they stories from parent-teacher meetings to discuss your progress?
Two school friends smiling.

Stories of Old…

If you met with old school friends, what stories would you reminisce over?

  • Stories from school.
  • And outside in your free time.
A heated discussion in a meeting.

Important Work Lessons

What are some important lessons you learned at work?

  • How did you learn these lessons? Through best practices and excellent role models, or by making mistakes?
  • Are there a few key lessons that young workers could benefit from?
Three workers share a joke at work.

Funny Workplace

What funny stories do you have about your workplaces?

A lady in a field, having to choose one from two paths.

Career Changes?

Looking back at your career path, would you make any changes?

A lady speaking publicly about something she is passionate about.

Revisit Special Moments

If you could revisit special moments in your career, which would they be?

  • Do you have any photos from these times?
  • Do you have any stand-out, impactful or important moments in your career, even if you don’t want to revisit them?

List of Jobs

Can you list in chronological order every job you have ever had?

A lady at work, turning back to someone and smiling at them.

Reminiscing Over Work

If you met with old colleagues, what stories would you reminisce about?

  • What were the good times you shared?
  • When did you face hard times together?
  • Did you enjoy spending time socially?
  • Do you have any photos from back then?
A lady performing a scientific test.

Starting Again

If you had to start a career in a new industry, which would you choose and why?

  • A career in a certain industry can take time to build. But the industry can change, and may no longer be as appealing.
  • If you could work in a different industry would you?
  • What don’t you like about your current industry?

Tips and Advice

Do you have any career tips or professional advice?

  • It may be general advice about work-life balance.
  • How to build strong relationships at work.
  • How to write a compelling CV and excel at interviews.
  • Any tips you wish you had known at a younger age?

Story Prompt FAQ’s

What is ‘work and education’?

‘Work and education’ stories share insights that others can learn from and are an enduring record of how much the school and work experience has changed. New technologies and changes in society mean that your intellectual journey through life is going to be unique. So capture it in stories as a piece of family history, and help others by sharing the lessons you learned along the way.

What are ‘Story prompts’?

Sometimes it can be hard to get start writing a story. Story Prompts help by providing creative ideas as inspiration. Simirity’s Story Prompts have been designed to ignite discussions in your family and inspire you to ask questions about your family’s past.

How can I use Story Prompts with my family?

Stories don’t have to be written, they can be spoken too. They are designed for both you and your family. As you review the prompts, consider how your parents or a sibling might answer. It you don’t want to write a story down that fine – they can serve as great inspiration for interesting family discussions.

All prompts are built into the Simirity App. Within the app, you can send them to family members as Story Requests. This is a great opportunity to ensure important family stories get discussed and preserved for future generations.


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