Signing up for Social Security

Mix good news and bad news and get mixed emotions. I signed up for Social Security, I think. Should I have waited? Sure. Should I have signed up earlier, definitely in retrospect. Was it easy or hard? Yes. No. It either took a half an hour or seven months. It’s mixed.

Despite perfect storms of bad luck, I am an optimist. Sometimes that has a cost. In terms of making money, of paying my bills, I have worked and am working at many types of jobs and businesses. Just check out my bio on this blog and other sites: Real Estate Broker, Consultant, Writer, Speaker, Teacher, Photographer, Engineer, Entrepreneur, etc. Yes, we were all hit with the pandemic; but surely some mix of things on that list will create enough value to accrue to enough income to pay those bills. 

OK. I admit it. Public speaking wasn’t going to well during a pandemic. The same with teaching. I’ve been out of engineering for long enough that it wasn’t much of an option (so say so many ghosted job applications). Consultant? Sure! Crisis is an excellent time to reconsider old ways and either adapt or innovate, ideas were launched. Maybe someday they’ll pay. Photography continues, with pay in the form of compliments. Writing, as always, and optimism about my first sci-fi novel; but that might not be done for a year or two. Real estate has been the thing. I’ve worked on it almost every day; but alas, too many people were priced out of looking, too many were outbid, and too many decided to move to places more affordable than Whidbey Island. The entrepreneurial spirit, however continues, one sign of the optimist.

So much for the plans and the optimism. The reality is that bills must be paid, my main stock has been slipping (come on, MVIS!), and a stimulus check is in the mail – seemingly eternally. 

Hello, Social Security 

No, really. “Hello, Social Security.” I ended up calling them, twice.

Try Online

Back to the beginning. This financial situation was apparent months ago. I dutifully went to their web site (, started answering questions, reading FAQs, and being intimidated by the possibility of a time-delaying byzantine bureaucracy when finding quotes like;

Apply four months before you want your Social Security retirement benefits to start. If you want your benefits to start at age 62, you can apply at age 61 and eight months.

At least I have the age thing done. Patience and perseverance will do that.

What else in addition to name, address, Social Security Number, and contact info?

  • Dates of current and previous marriages, and where you were married
  • Employer names and dates for the past two years
  • Self-employment income and type of business
  • Bank information to set up your direct deposit
  • Your original birth certificate
  • A copy of your W-2 tax form(s) and/or self-employment tax return from last year. A photocopy is acceptable

But, according to the site, don’t take your time about it because;

For security reasons, the online application gives you a warning if you leave it open and don’t do anything for 25 minutes.

OK. This is going to take a while; but I’ll have to do it quickly. No paradox or contradiction there.

Filling out government forms about important personal matters gives me anxiety attacks. Digging up all of those old records? Not easy. I keep such things, but which boxes hold what and how much time would I have to spend in the attic battling spiders? (But not rodents, thankfully.) Humans help me at times like this.

Try Email

This step was quick. After a few exchanges that may have included Chats or Texts (a rare time when I didn’t take notes) I compiled a list of questions. 

  • Dates of current and previous marriages, and where you were married. (Are Marriage Licences and Dissolution Documents required or can memory suffice?).
  • Employer names and dates for the past two years. (All income has been earned as an independent contractor. Do I need to include the names of businesses that used my services, in particular, real estate brokerages?)
  • Self-employment income and type of business. (Do Schedules C and SE suffice, or should I include the complete 1040 package?)
  • Does email suffice or are hardcopies required? 

They answered by giving me a phone number to call. 

Try Phoning for Help

Twenty minutes after calling, which is short or long depending on your experience, perspective, and tolerance for voicemail music, someone answered. I received some relief because they can confirm many of the details; so, they just needed the information. I didn’t have to contact the hospital I was born in and ask for an official paper copy of my birth certificate, etc. Whew.

  • Dates of current and previous marriages, and where you were married. (Later I’d find that it was a good thing that I saved the Divorce/Dissolution Documents even though memory suffices. Flipping through the wedding album was a different memory experience.)
  • Employer names and dates for the past two years. (As I understand it, this is only about W-2 type jobs. None of those.)
  • Self-employment income and type of business. (Ah, this is almost all of my recent work, Gig Economy, 1099 stuff. Though I did get to freak out in June when I couldn’t find my 2020 tax package filed in April 2021 . My accountant had a backup. Whew.)

The person helping me was nice and answered lots of questions about estimated benefits, timing, and alternatives to signing up immediately. I thanked them and hung up because I knew it was going to take some time for me to gather the information. They might be fine with my best guesses, but if I had the information I’d feel better gathering it in case they called back. Signing up later could mean better benefits. It was November 2020. Surely people would wear masks and vaccinate now that we knew what we were fighting. Business would return and would chase away the need for signing up for Social Security.


A bit of procrastination, layers of failed or maybe just delayed optimisms, and the repeated advice from several friends who signed up early finally convinced me to try signing up, again. An enormous bill from my homeowners association that matched a still-delayed stimulus check helped, too.

So, about seven months later I checked my notes, rummaged around (and actually emptied) the attic, found more old documents, and called the Social Security helpers. 

On The Phone Again

Start with another twenty minutes of repetitive electronic music. At least I got some meditation done.

They dutifully started by advising me to wait for my full retirement at 67, five years from now. If my bills could wait, that’d be great. We just went through this pandemic, remember? Glad they had a sense of humor when we discussed my recent income.

We talked about how I’d been earning, or trying to earn, money. After hearing my list they pointed out that as my business returned, some of the Social Security benefits would be offset against any business income I received. Some might complain about losing those benefits, but I’d cheer having that much income (and hopefully more.) Besides, they couldn’t take more than they’d give. (The IRS, however, wasn’t part of the conversation.)

They provided my estimated benefits, which were about 22% less than the estimate I received in the previous call. Sad. But were more than half my frugal life expenses. I’d be able to pay the mortgage and things like insurance or utilities. I’d still have to make more for the rest. Better than nothing, which is what I was working from as I called.

Within fifteen minutes they steered me through all of the questions; and they did so with manners and impressive people skills. 

And then told me that they’d set up my appointment. My appointment? I thought this was my appointment! Nope. This was just to prepare everything now to make that in-person meeting more efficient eventually. The soonest slot available was in August. I asked if we could expedite it by going to another office, even if it was two hours away. Yes. Maybe. Hard to say for sure. Of course I could just go online and there’d be no need for the appointment. 

As Inigo says in Princess Bride; “You told me to go back to the beginning… so I have.

Hello Online, Again

This time was simpler. It’s not that the process had changed, but those two heroic or at least patient and understanding people answered so many of my questions that this time through was much easier. In twenty-five minutes I answered all of their questions, guessed and estimated as necessary, and rushed along so my momentum would carry me through the hurdles of anxieties that were ready to pounce if I felt a doubt.

According to one of the last bits of information from the person I talked to, by signing up online that conservative four-month wait for the first check might be as short as two months, August instead of October. The caution, however, is that they might need to clarify information. Evidently, guesses can cause delays.

Implications And Emotions

The mix of emotions is taking time to process. That’s partly what writing this blog helps me do (though the main goal is to help others by chronicling a real experience instead of the version in some brochure.) Those years of work will literally pay off, but they only pay for half of what I need. Receiving those benefits can remove the stress of many basic needs, but it also feels like a capitulation and an admission of failure. Just as with my IRA, the less money you have the less money you receive. I had to gut my IRA prematurely because of My Triple Whammy, which also meant paying a penalty on my retirement funds. By using an IRA I now also have to pay taxes on losses that I could’ve balanced against gains if I’d left all of those investments in conventional accounts. Signing up for Social Security out of necessity, not choice, means my current lack of security reduces the amount of security I am provided. And yet, I’m glad the benefits are there, though I’ll be happier when they are here.

Now, the wait begins. Because they may need to clarify items, and because bureaucracies can have issues, I won’t consider this task concluded until the first deposit is made. 

In the meantime, I’ll continue to work because even after that deposit is made I’ll continue to need additional income – at least for now. I could sell my house, possibly move as a result, watch my portfolio for some semi-passive asset growth, hope my books or photos or both sell online for passive income, and we’ve just come back around to where I started: optimism and entrepreneurship. Wish me luck, good luck, specifically. Now, about those lottery tickets., and maybe succeeding in ways I can’t imagine…

About Tom Trimbath

real estate broker / consultant / entrepreneur / writer / photographer / speaker / aerospace engineer / semi-semi-retired More info at: and at my amazon author page:
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