Does Looking Back on your Career Hold the Key to your Future?

Jane Horan
4 min readJan 3, 2022

Steve Jobs famously said “You can’t connect the dots looking forward; you can only connect them looking backwards.” To move forward in your career, you must look back, from where you’ve come.

When we’re exploring new opportunities, we may not exactly know what we’re looking for, that nagging feeling for something than what we’ve already done different to what we’ve done, and not know what ‘different’ looks like. And we probably have a sense that something about our current situation is ‘off’’ — although can’t define it clearly.

The reason? Most of us are terrible at predicting what will bring us happiness.


Because we’re influenced by outside forces, which separates us from our true selves. It gets more complicated when career choices like money, status and the wider job market overrides our true career drivers -and our true selves.

To land the job you really want, be clear about past events that made you feel authentic, purposeful, and happy. Those moments hold important clues about where you should be going next.

Why look backward to look forward?

When I coach mid-career professionals they’ll often recount a list of their experiences, credentials and skills, in chronological order. Their accounting tends to be meticulous, the CV impressive. But few can answer the most important question — ‘why does a career shift make sense for you right now, and what are you interested in pursuing next?’

If you, can’t answer this question, it’s going to be difficult to bring about positive change you may want this year.

To get unstuck, be really really clear about what you want and need from work. A helpful way to identify these wants and needs is to look back on your younger self and what was important to you.

Analyzing your past experiences gives:

An objective assessment: What motivated, excited and engaged you in the past — and what makes you stressed, anxious and indifferent? Plotting each experience against a timeline can shed significant light on what you should and shouldn’t be doing next.

Understanding to your ideal work environment: We know certain work environments provide a better experience, regardless of the actual role. For instance, someone who enjoys a start-up environment may not necessarily enjoy steady corporate growth. Examining those past experiences — and acknowledging how you felt each time — reveals preferences, which may not show up on skills or aptitude tests.

A positive mindset: If you feel directionless, recall the last time you were happy and felt like yourself, whatever and wherever it was. Such reflections shift you towards a more positive state and with the good things you’re doing — what’s going well in your life. If you structure your career planning around these deep-seated, positive passions, you’ll be standing on solid ground.

A practical plan: It’s more sensible to speak and make decisions based on your own real, tangible and familiar experiences than to imagine an abstract future that is open to too many possibilities. The greater the certainty the less the anxiety.

Which past experiences will build your career?

Everything has value, so ideally you’ll write the narrative of your life from start to finish. That can be challenging, so here are some questions to help you find your story:

● Examine your career: Would you do it all over again? Are there any steps you regret?

● What are you proudest of professionally?

● At work where do you lose all sense of time and ego?

● Which events made you excited, outraged, yearning to go out there and make a difference?

● What’s one of your best traits? And another?

● Who do have a strong relationship with? Why him or her? And why do you think they chose you?

● When you look back at those early passions and interests, which areas did you excel in as a teenager? Dance, sports, music, chemistry or English? Are any of those affinities still in your life?

● When did you last feel a deep sense of purpose?

● In which situations have you not thrived? Which times were you most unfulfilled. Why?

● When were you at your most confident and willing to take risks? What made you energized and fearless?

These questions are to help you dig deep and create new thoughts. Please don’t answer them superficially, tempting as it may be. Stop, truly stop and just think for a moment to pull in new ideas and connections in your reflections.

Those are your powerful “Aha Moments” and allow you to build your truest narrative.

What’s Next?

Once you’ve examined and accepted the key experiences in your earlier life, craft them into a career story, adding context to render all past experiences meaningful. You start to see causality and to up-play that which made your past career remarkable, rather than thinking your previous achievements were uninspiring to anyone else. Your career story will show otherwise.

This can help reassure you that your future plans make sense — and that you haven’t thrown everything away by making a shift in your life!

Make a start.

Be curious.

Revisit your past.

Take time to listen.

It’s the first step to purposefully control your career transition, rather than having it control you.



Jane Horan

Author. Helping people find meaningful work. I write monthly on inclusion, political savvy and careers and how these interconnect.