Most digital problems aren't caused by a bad system. They're caused by a good system nobody has looked at in four years — a backup that stopped running in 2023, a subscription renewing for a service that shut down, an emergency contact list naming someone you've lost touch with.
Digital things fail silently. Nothing tells you the backup stopped. That's what an annual review is for.
This takes about three hours. Do it in one sitting or spread it across a month. January works, or pair it with tax season when you're already handling documents.
Part 1: Files (45 minutes)
☐ Archive last year's completed material. Move finished business into 06-ARCHIVE: last year's taxes once settled, closed accounts, sold-property records, completed projects. Active folders that stay small are what make everything else fast.
☐ Discard anything past its retention period. Routine statements older than a couple of years, expired warranties, superseded document versions, tax-supporting material older than seven years. Shred paper containing personal information.
☐ Empty the pending-delete folder. If you moved things to a holding folder last year and haven't retrieved any of it, delete it.
☐ Clear Downloads and the desktop completely. File the keepers, delete the rest.
☐ Check the 99-TO-SORT folder. If you haven't needed anything from it in twelve months, move the whole thing to Archive and stop thinking about it.
☐ Update your filing notes. The text file recording where ambiguous documents go. Add any decisions you made this year.
Part 2: Backups (30 minutes)
This is the most important section. Everything else is convenience; this is the difference between an inconvenience and a catastrophe.
☐ Confirm the backup actually ran recently. Open your backup software and check the last successful run date. If it says eight months ago, you found the reason to do this review.
☐ Restore a file and open it. Not a test of the software's claim — an actual restore. Pick a document from two years ago, restore it from the backup, open it, confirm it's correct and not corrupted.
This is the step everyone skips and the only one that proves the backup works.
☐ Verify the offsite copy specifically. This is the one that quietly fails — an expired card on a cloud subscription, a drive at a relative's house nobody has swapped since 2023. Check its date.
☐ Check that new material is included. If you added a photo library, a new drive, or a new folder this year, confirm the backup covers it. Backups protect what they were configured to protect, and configurations don't update themselves.
☐ Check drive health and age. Mechanical drives commonly last five to seven years. If your backup drive is older than that, replace it now rather than after it fails. Note the purchase date somewhere.
☐ Export from cloud photo services. Twice a year is better, but once is far better than never. Google Takeout, or export from Apple Photos, into a library you control on a drive at home. Cloud services are sync, not backup — an account lockout takes everything.
Part 3: Security (45 minutes)
☐ Check whether your accounts appeared in a breach. Use a reputable breach-checking service with your email addresses. Change the password anywhere it shows up.
☐ Change reused passwords. Most password managers will flag reused and weak passwords in a security audit. Start with email, banking, and anything holding payment details — email especially, because it's the reset path for everything else.
☐ Turn on two-factor authentication where it's missing. Priority order: email, banking, password manager, cloud storage, social media. Prefer an authenticator app over SMS where offered.
☐ Save your backup codes. Two-factor backup codes are useless if you can't find them. Print them or store them in your password manager, and make sure the codes for your password manager itself are stored somewhere else entirely.
☐ Review connected apps and third-party access. In your Google, Apple, Microsoft, and social accounts, look at which third-party apps have access. Revoke anything you don't recognize or no longer use. This list is usually longer and older than expected.
☐ Check active sessions and devices. Most major accounts show every device currently logged in. Sign out anything unfamiliar, plus devices you no longer own.
☐ Update your recovery information. Recovery email and phone number on your main accounts. If your recovery phone is a number you gave up in 2021, you're locked out of your own recovery path.
☐ Update your emergency contacts and access. If you use a password manager with emergency access, confirm the designated person is still the right one and still knows they're designated.
Part 4: Money and subscriptions (30 minutes)
☐ Audit subscriptions against twelve months of statements. Twelve months, because annual renewals only appear once. Check card statements, app store subscriptions, and PayPal automatic payments separately — they don't all show up in the same place.
☐ Convert everything to annual cost and total it. "$9.99 a month" and "$120 a year for an app I opened twice" are the same fact and produce different decisions.
☐ Cancel what fails the question. Not "is this worth $12 a month" but "would I sign up for this today at this price."
☐ Check for quiet price increases. Insurance, internet, and streaming raise rates without announcement. Some are negotiable.
☐ Verify your bill calendar is accurate. New bills, cancelled ones, changed amounts, changed payment cards.
☐ Confirm autopays are still pointed at valid cards. Especially if a card was reissued during the year.
Part 5: Accounts and devices (30 minutes)
☐ Close accounts you no longer use. Every dormant account is a place your data sits waiting to be breached. Old shopping sites, forums, services you tried once.
☐ Delete apps you haven't opened in six months. Then check whether deleting the app left a subscription running.
☐ Update your device inventory. Model and serial numbers for anything you own, useful for insurance claims and theft reports.
☐ Wipe and dispose of old devices properly. That drawer of old phones and laptops holds your data. Pull anything you need off them first, then sign out of accounts (this releases activation locks), then erase. Recycle or donate.
☐ Refresh your home contents video. Ten minutes walking through your house filming every room, opening closets and drawers, narrating what's inside. Store it offsite. This is the single most useful thing you can do for an eventual insurance claim, and it should be redone every year or two.
Part 6: The things nobody checks (20 minutes)
☐ Update your locator document. The one-page note saying where everything is — safe location and code, backup drives, password manager access, attorney, accountant, insurance agent, policy numbers. Give the updated copy to whoever would need it.
☐ Confirm someone else knows the system exists. An archive nobody knows about doesn't help anyone. At minimum, one other adult should know where your documents are and how to get in.
☐ Check your emergency document kit. IDs, birth certificates, insurance numbers, medication lists, doctors, emergency contacts. Are the medications current? Is the contact list still accurate?
☐ Check expiry dates. Passports (many countries require six months' validity), driver's licenses, registrations, professional certifications. Set reminders for anything expiring in the next eighteen months.
☐ Verify your will and beneficiaries. Beneficiary designations on retirement accounts and life insurance override your will in most jurisdictions. If your circumstances changed — marriage, divorce, birth, death — and you didn't update these, they're still pointing at whoever you named years ago. This is one of the most common and most consequential oversights in this entire list.
☐ Save voicemails and messages from people who matter. Voicemail systems delete on their own schedule, and phone upgrades lose them. If there's a recording of someone's voice you'd want to keep, export it to a file this year.
Part 7: Photos (20 minutes)
☐ Import the year's photos from your phone into your real library. Cloud photo services get photos off your phone; they don't get them into an archive you control.
☐ Sort them into the year's folder and name any events worth naming.
☐ Purge screenshots. Anything older than a year, plus the current year's expired ones.
☐ Add to your highlights folder. The best 10 to 20 from the year. This is what makes a photo library get looked at instead of merely stored.
☐ Make a photo book. Optional and genuinely the highest-value item on this list for the long term. A book on a shelf survives indifference in a way no drive does.
Do these five if you do nothing else
If three hours isn't happening this year, do this instead — thirty minutes:
- Restore a file from your backup and open it. Confirms your backup works.
- Check that your offsite copy is current. Confirms you'd survive a fire.
- Audit twelve months of subscriptions. Usually pays for the time several times over.
- Turn on two-factor authentication on your email. Your email is the reset path for everything else you own.
- Update your locator document and tell someone where it is.
Those five cover the catastrophic failure modes. Everything above them is refinement.
Next in this series: How to Reorganize Digital Files After a Move or Life Change