Some Advice for Retail-to-Software Career Changers

Ian Carroll
3 min readJun 27, 2017


Have you ever had a demanding boss? I don’t just mean one who expects quality work, I mean someone who is a Boss. Capital B.

They give you ultimatums, and demand no back-talk. When they ask whether or not you can do a task the answer is “Yes Sir! Right away, Sir!”

But that’s a lie.

That might sound harsh, but that’s a fact. Lies, by definition, are when words don’t relate to reality. If the answer has to be “Yes” regardless of what the task is, the word no longer has any relationship to reality. But that’s what the Boss demands. What they don’t tell you is that they know it’s a lie. They know it can’t be done.

But they command it anyway, and command you to do it knowing full-well you will fail.

They lie.

You, the employee lie right back.

You say “Yes, Sir! Right away, Sir!” When you know what’s been asked of you can’t be done.

And of course you fail at the task. It. Can’t. Be. Done.

But the Boss doesn’t say anything about it. As a sign of his generosity, he let’s you off the hook. You now owe him a favor, and his authority increases. Next time he asks you to do something, you’d better lie to him and tell him “Yes, Sir, Right away, Sir!” After all, you owe him for overlooking your last failure. You are afraid to say the truth. And you are trapped in a vicious cycle of lies.

Fear may be a great motivator, but it will eventually end in everyone’s destruction, Boss and employee alike. Never mind the hapless clients who are unfortunate enough to encounter this business. The Boss is trading the value of the company for his personal control. The employee is trading her personal value to keep the Boss happy. This situation will limp along, losing value to this lie until the employee or the company collapses.

I’ve lived this lie. Multiple times. And I have to say, you can’t think this way and maintain a career as a professional of any kind, let alone a software crafter. Clients deserve to be told honestly what can and can’t be done.

It’s so easy to tell someone “Yes.” It instantly makes them happy. You are transformed into Jonny-on-the-spot. But it is still a lie. And when it comes out that your words could not hope to match reality, which it will, trust will be lost. And trust is the foundation of all of the respect others hold for you as a professional.

The differences between a conscript and a crafter is trust, integrity, and agency. A professional’s opinion is trusted. Their personal integrity is what builds that trust. That trust in turn grants them agency to make decisions. When you lie by saying things are fine when you know they aren’t, even if it was with the best of intentions, you loose everything. You cease to be a professional.

Telling the truth takes courage. And it’s not something a lot of retail workers are allowed to have. In retail, you have to fight for every scrap of integrity. If you’re lucky, and you sacrifice your promotion opportunities, you might hold on to some of it without getting fired.

But when you change over to a career in software, you’ll need to put the fear of saying anything other than “Yes” behind you. It has no place in maintaining good relationships with your new clients and peers. You must have the courage to say the truth. Even when it disappoints people. Even when everything you’ve learned to keep yourself alive is telling you to just say “Yes Sir! Right away, Sir!”

If you’re a retail worker looking to immigrate to the shining frontier of software development, let me wish you the very best of luck. Software needs you. But if you’ve been in retail for any amount of time, the Boss is not just in the store anymore. He’s in your head. You carry him with you wherever you go. So watch out for the Boss, and practice fighting your instincts by telling the truth. It’s harder than you think. But you will respect yourself so much more for having the courage to do so.



Ian Carroll

Software Crafter at 8th Light Consultancy, Organizer for Fullstack LA meetup, Eagle Scout, Theatre Person, Taoist Philosopher among other passions.