Something to doWhat's next
Talk to someone five years ahead of you
A simple exercise to borrow hindsight from someone further down a path you might take
Why it’s worth your time
People a few years down a path remember what surprised them, what they'd skip and what they wish they'd started sooner. That hindsight is hard to get any other way, and many people are glad to share it. Asking what they wish they'd known gets you advice rather than a sales pitch for their choices.
How to get career advice from someone a few years ahead
You’ll come away with a few hard-won lessons about a path you're considering, from someone who's on it.
We’ll turn this into a checklist you can tick off.
- Name the path you're curious about.
Be specific: managing people, moving to a startup, going independent, switching from engineering to product. A clear path makes it easier to find the right person and ask the right questions.
- Find someone about five years down it.
A former colleague, a friend of a friend, someone from your school or an old company. Five years is a guide: recent enough that they remember the early choices, far enough that they've seen how those played out.
- Ask for 30 minutes, and say why.
Keep the ask short and specific, and make it easy to say no.
To: someone further down the pathI'm thinking about a move toward the path you're considering, and you're a few years into exactly that. I'd love to hear how it's looked from the inside.
Would you have 30 minutes in the next few weeks, for a call or a coffee? Mostly I'd like to ask what you wish you'd known at the start. Completely fine if now isn't a good time.
Swap the highlighted parts for your thing. Works on Slack, in email, or said out loud. - Ask what they wish they'd known.
Then follow their answers. Ask about a moment they nearly went another way, what the path costs that nobody mentions, and what kind of person seems to thrive on it.
You“Looking back, what do you wish someone had told you when you were where I am now?” - Thank them, and tell them what you did with it.
A thank-you the same day, and a short note a few weeks later saying what you tried or decided. That second note is what turns one conversation into a relationship.
Good moments for this: while you're weighing a movebefore a big career decisiononce a year, with someone new
We’ll turn this into a checklist you can tick off.
Keep going with Truest
Small actions add up. Truest helps you find the next thing worth doing, make the space to do it, and keep a record of your progress. It’s a private place to work on your career, and it’s yours, not your employer’s.
- It actually happensDo it now, and you’ve invested in your career today.
- Kept with the thing it was aboutSave what comes back in your Vault, next to the work it was about.
- It’s yours to keepEach thing you do is saved to your private record, there when your next review or job search comes around.
Anything else we can help you with this week?
Making it work for you
Every workplace is different. Here’s what to think about before you start, and what might get in the way.
Things to think about
Their story is shaped by their timing, their company and their luck. If you can, talk to two people and listen for what they agree on.
What might make this harder
Ask former colleagues who they know, try alumni groups, or look for people who write or speak about the work. A warm introduction helps, but a thoughtful cold note often works too.
Questions people ask
How do I ask someone for career advice?
Keep it short and specific: say what path you're considering, why you thought of them, and ask for about 30 minutes. Make it easy to say no, and thank them properly afterward.
What questions should I ask someone further along in their career?
Start with what they wish they'd known at your stage. Then ask about a moment they nearly chose differently, what the path costs that people don't mention, and who tends to thrive.
How do I know if a career path is right for me?
Talking to people a few years into it is one of the best ways to find out, because they still remember the surprises. Listen for whether the hard parts sound like things you'd accept.
Is it weird to ask a stranger for career advice?
Not usually, if the ask is respectful and specific. Many people enjoy sharing what they've learned, especially with someone at a stage they remember.
Why this works, and where it comes from
The most useful career advice often comes from people only a little further along. Someone twenty years ahead may be describing a world that has changed; someone six months ahead hasn't seen enough yet. A few years down the road is where the surprises are still fresh and the consequences have had time to show.
This is a cousin of the informational interview, with a different aim. An informational interview asks what a job involves. This asks what a path does to you over time: the choices that mattered, the costs nobody mentioned, the things they'd start sooner. It's less about the work and more about the arc.
The question is shaped as advice on purpose. Asking someone to evaluate their own career can put them on the defensive, or into sales mode. Asking what they wish they'd known invites them to help you, which is easier to do well and tends to be more candid. People give better advice than verdicts, especially about their own choices.
If you already know the path and need a way in, ask for that plainly instead. An introduction, a referral or a look at how their team hires is a different request, and it's kinder to make it directly than to tuck it inside a conversation about hindsight.
Other simple things to consider
More in What's next
See allRead this alongside your role page
Tell Truest what you’re dealing with
We read every one, and we write guides for the things that come up most. Leave your email if you’d like to hear when we do.
An exercise written by Truest, based on our experience. Last updated October 2, 2026. We sell a career membership; where that’s relevant above, we say so.