In many ways, I love living in the digital age. As someone who grew up in the analog world (my first journalism job, as a college intern, involved a manual typewriter and carbon paper), I am still delighted to be able to find out, within 10 seconds, whether a particular movie star is still alive or to share my latest column with the entire world through a social media post.

But the downside of digital life is driving me batty – so much so that I sometimes consider trying to go off the grid altogether to seek a less frustrating existence. I have a fantasy of this simple life that I describe as Full Bore Thoreau. It involves listening to birdsong and reading Russian novels while occasionally using a landline to maintain contact with other humans.

What has brought me to this point? Consider, as one of many examples, my recent adventures with usernames and passwords, involving E-ZPass, the device that allows you to travel through toll barriers without stopping to hand over cash. When I signed up for it many years ago, I apparently got a username and password. And I gave them my credit card information so that it could be charged when necessary.

All went well for years; I would get hard-copy statements in the mail from time to time, but never kept them around for long. I gave this arrangement no thought, until the day I got a voicemail message, claiming to be from a law firm, saying I had accrued massive E-ZPass debt.

I thought it might be a scam so decided to check my account balance, something I had never felt the need to do before. Signing in involved that original username and password. But, horrors! It turned out that my username was not my email address. I tried to retrieve it via my cellphone number or email address but only descended into concentric circles of digital hell. A phone call – old-school, I know – to customer service resulted in a demand for my account number, but in order to get that, I needed to, yes, sign on to my account. Round and round I went.

Of course, an issue like that is minor, one tiny piece of the daily puzzle that involves all the ways that we (and institutions like banks or employers) try to protect digital security. Two-factor authentication now stops us at every turn. To log in, you need to put in the code that’s just been sent to your phone, but as you go to your text messages to find it, the original question somehow has disappeared into the ether.

Those of us who do any freelance work descend to a special torture chamber that comes with registering as a “vendor” with part-time employers. This involves layers upon layers of proving your identity, submitting tax forms and navigating multilayered payment systems with weird names and byzantine processes. Not long ago, I got an email from the accounts payable department of a large media company that began with this less than promising line, including the capitalized F: “Your Form has been received and forwarded for processing.” It then directed me to the “secure onboarding portal”, where many other incomprehensible steps awaited.

All of this, I remind myself, is a result of privilege. These are the very definition of first-world problems, and I’m lucky – in a sense – to have them. But it doesn’t feel that way. Often, I wish I could step off the digital merry-go-round.

At best, such challenges help me to develop patience as I plod through the steps, ask for help when possible (often from a digital native, possibly including my son or daughter), and eventually solve the problem – as I did with the EZ-Pass puzzle.

The solution there, it turned out, was marvelously old-fashioned. I dug out a small notebook from a drawer, filled with scrawled usernames and passwords going back for years. And there the answer was, in all its inky glory. My login was successful, my account balance was fine, and I deemed it unwise to respond to the self-described lawyer.

Victorious for the moment, I moved on to the inevitable next hassle, while dreaming of fishing for my meals from the banks of Walden Pond.

• Margaret Sullivan is a Guardian US columnist writing on media, politics and culture