How to Learn New Skills on the Job Like a Pro by @projectmaven

My first temp position out of college was working as a bookkeeper for a photographer’s agent in NYC. Although I had never been a bookkeeper before, I was good at math and thought, how hard could it be? The first day I showed up at the office, my boss handed me a shoebox full of receipts and a column pad and said, do something with this. So I did. And I was right, it wasn’t that hard.

Before long, I was mapping out her income and expenses with ease, so reconciling the monthly bank statement also became part of my job. I began to notice some discrepancies with one of the expenses – the weekly paychecks for my co-worker, the office manager. I discovered she had been writing extra paychecks for herself. When I reported it to my employer, she was fired and brought up on charges. And that’s how I got my first promotion.

In my next office job managing an alternative health care practice, which lasted well over a decade, I started out doing handwritten expenses and payroll for our three person team. By the time I left that position, I was overseeing electronic payroll for a staff of eight, patient and staff scheduling, medical billing, inventory as well as employee benefits, hiring & firing, plus all marketing and outreach including newsletters, health fairs and other promotional campaigns.

If you stay in a position long enough, presuming there is a need and you are willing to do what it takes, you can learn nearly any skill you need to learn. This is one good reason (besides financial stability) why people stay in jobs for long periods of time. If a position offers the opportunity to learn new skills, it keeps it challenging and interesting. But there are some things to remember when learning new skills on the job:

Ask Lots of Questions

It’s one thing to be confident. It’s another to act like you know what you’re doing when you don’t. There’s no shame in “not knowing.” In fact, how can you actually learn anything if you already “know” everything? I was lucky to work side by side with a great accountant who taught me a lot about small business management, budgeting and financial planning, as I prepared the books for him year after year. It felt good to be a perpetual student under his tutelage. The knowledge I gained in that position has benefitted me to this day.

Don’t Be Afraid to Make Mistakes

Making mistakes is one of the best ways to learn. It teaches you to think on your feet, to solve problems and to try new ideas. The most important thing about making mistakes is to LEARN from them. If you are growing your knowledge base and taking on new responsibilities, most employers will extend a certain amount of latitude as you exercise your learning curve. Where they may run out of patience, though, is if they see you making the same mistake over and over. Learn your lessons, and make adjustments. Making mistakes becomes a waste of time if you don’t grow from the experience.

The Extra Challenge for Freelancers

If you’re self-employed, learning new skills on the job is even more challenging. Without a direct supervisor or a manager, it’s really all on you to implement new knowledge and techniques into your regular routine. This is where a good circle of colleagues is essential. I find that having a strong community of industry professionals is the best way to stay on top of the latest productivity tools and other practical information. Educational and networking events like techsytalk LIVE are a great way to stay on top of the latest developments and share information with your peers. You may find that you have as much to teach as you do to learn. Staying in the flow of this kind of exchange will keep your business fresh and enlivened by strong relationships.


  1. Hi, Deborah! Not being afraid to make mistakes will make one more open to experiencing new things and learning more skills. Nice article–very well-written!

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