There's no rule, but there is a test, and it takes four seconds.
Open your LinkedIn profile. Look at the photo. If this person walked into a meeting, would the people waiting recognise them immediately?
If you hesitated, you have your answer.
The rough number
Every two to three years for most people.
Photos don't expire. Faces, hair, glasses and job titles just drift, slowly enough that you stop noticing. Your photo never looks wrong to you, because you've watched it age alongside you. It looks wrong to the person meeting you for the first time.
Two years is a sensible default. Some people stretch to five and get away with it. Others need one after eighteen months because everything about the role changed.
What resets the clock immediately
Ignore the calendar if any of these happened.
You changed how you look. New glasses, a beard arriving or leaving, a real change in hair. Glasses are the most underestimated of these — they restructure a face, and half of all "you look different in person" comments trace straight back to them.
You changed seniority. A photo that read as approachable and junior carries differently when you're pitching as a partner. The image should match the room you walk into now.
You changed industries. What reads polished in tech reads casual in law. What reads right in law reads stiff in creative.
Your team page is a patchwork. Three photographers, four backgrounds, two decades. That page isn't communicating credibility; it's communicating that nobody owns it. This is the usual reason an entire team books at once.
Someone said "oh, you look different." They're being polite. That sentence means it's been too long.
What it quietly costs
Your headshot works whether you maintain it or not.
For most professionals, more people see that photo in a year than meet them in person. It's attached to every connection request, proposal, conference programme, article and internal directory. First impression inside a first impression, running unsupervised.
An outdated photo doesn't announce itself as outdated. It reads as slightly off, and people rarely identify why. It opens a small gap between who they expected and who arrived, at exactly the moment you'd rather be building trust than spending it.
The expensive version is subtler: a photo from a stage of your career you've moved past, quietly undercutting the seniority you're currently claiming.
What "updated" doesn't mean
It doesn't mean looking younger, and it doesn't mean a heavily retouched version of yourself. Those create the same mismatch from the other direction — the person who shows up doesn't match the picture, except now it's your doing rather than time's.
A current headshot looks like you on a good day, in clothes you actually wear to work, in the year you're actually in. Recognition, not flattery.
A rhythm that works
On your own: book when something changes, and otherwise set a reminder two years out. Ten seconds of admin now beats the awkward realisation later.
As a team: new starters once a year, full refresh every three. Keeps the page coherent without it becoming a standing project.
Before anything with a stage: conferences, panels, award submissions, a website relaunch. Each publishes your photo somewhere permanent, at higher resolution than you expect, next to people who updated theirs.
Back to the test
Open the photo. Would someone waiting in a lobby recognise you?
If yes, you've got time. If you hesitated — or caught yourself explaining why it's still basically fine — the hesitation was the answer.
Sessions run Monday to Friday in London, Ontario, take about an hour, and you'll see the images as we shoot and choose your favourites before you leave.