5 invaluable lessons from my first real job
28 years ago, my boss asked me to do something icky. Here's what it taught me.
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In my first new job after rehab, I was an assistant in a small office. The business was in a niche corner of lending for specific types of commercial real estate.
This small capital company was owned and run by a husband/wife team, and only had two or three other people on staff (including me). My job was to handle incoming calls, manage prospective and current customer files, produce correspondence, and file deal paperwork.
I liked the job and the people I worked with. After a few months, I was “promoted” to assist the Vice President in charge of closing the deals (loans). In this role, I’d research post office locations, gather necessary information from the clients, and keep them apprised of their loan process.
Everything was going well until one day, the VP asked me to brush off a client. For some reason, my boss hadn’t yet “locked” the loan, but the customer assumed we had. The VP asked me to tell the client it wasn’t yet done for specific reasons (that may or may not have been true—I wasn’t well-versed enough in the process to know).
When someone is buying real estate, the lender can lock the interest rate for a specific period of time (often 30, 45, or 60 days). A rate lock says, “No matter what happens to interest rates between now and closing, this is your rate.”
Until the rate is locked, the interest rate can go up or down—and it does, sometimes multiple times a day based on the broader financial markets. Small changes can have a big impact over a 15–30 year loan. A 0.5% increase in interest rate can mean hundreds more per month and tens of thousands more over the life of the loan.
TL;DR locking the rate was an important step in the lending process, and timing really matters.
I did communicate this to the client, and of course he was disappointed, and concerned that rates would go up. I reassured him we were working as fast as we could, which seemed to mollify him. I didn’t like having to relay this news, but hey, stuff happens. I was glad I could reassure him.
The escalation to icky
This began happening more often. It seemed like my boss had a strategy that didn’t always line up with what the client wanted to do. But, I figured, we had the experience here. We knew how these loans and the market worked. I assumed we were holding the line because that was best for the deal, and therefore the customer.
Until one day, when my boss asked me to flat-out lie to a client. This time, from what I had gathered, the VP was delaying the lock deliberately, assuming the rates would tick up the next day based on market conditions and predictions. My boss wanted to wait, because a slightly higher interest rate meant more money for the lender. (That was us.)
I did it. I lied to this customer, who trusted us to handle their business with competence and integrity. The person asking was my boss, and I needed this job. I wasn’t long out of rehab, I had tons of credit card debt (managing my credit score wasn’t high on my priorities when I was actively using), and I was living literally paycheck to paycheck. So I did as I was asked, and didn’t make a fuss.
But I didn’t feel good about it. At all. I understand how capitalism works. I know this person’s role was to generate profits. But doing so at the expense of a trusting client was taking things a giant step too far.
Had that been the only time, I might have let it slide. But that wasn’t the only time. Granted, this was a long time ago, but from what I remember from that time period, my boss started asking me to lie a lot. I don’t know if they were under pressure from the owners, if they were just unscrupulous, or maybe just disorganized, but it seemed like many loans weren’t being locked promptly, and clients were starting to get upset.
I went from enjoying this job to hating it. I went from being a great assistant to openly defying my boss, then being reprimanded by them and the owners. I didn’t want to tell the owners exactly what was happening, because what if they knew? And if they didn’t know, did I want to narc like that? What kind of retaliation might I experience if the owners took my boss’s side? I had virtually zero business experience at this point. I didn’t trust my own judgment.
5 valuable lessons
For a variety of reasons, I did not last much longer in that job. But despite this happening 28 years ago, I still remember the lessons I took from that role:
Listen to your gut. If it feels gross, it probably is gross.
Trust is hard-earned and incredibly quick to burn. Treat it as one of your most precious resources.
If profits are your only metric of success, you’ll feel pressure to step outside of your integrity to “succeed.”
Any boss who asks you to lie for them deserves to be narced on.
If your boss (or their boss) doesn’t have your back, this isn’t the right place for you.
Though that job was a million years ago and short-lived (compared to the roles I’d hold in the future), it clearly brought me to the values I hold today, as the CEO of Whole30. Though that job still leaves a bad taste in my mouth, I’m profoundly grateful I learned these lessons when I did, in someone else’s company. (The alternative is learning them the hard way, and burning my own brand.)
Have you ever been asked to lie by your boss? What kind of icky behaviors have you experienced? Did they help you craft a list of “non-negotiables” for roles going forward? Share in comments.




