Hi Kally,

I hope you’re enjoying motherhood!

I have a career question for you. I’ve been working remotely in inside sales, which we know is a just a step away from telemarketing, and it’s become a soul-killing job. I can’t take the hang-ups anymore, so I’m looking to go back into the workforce full time.

Here’s the dilemma: I’m going to have to reinvent myself. 

First, some background: I’ve felt trapped in this job for some time because of the convenience and the money. There’s no room for promotions or raises, and because of the position, I’ve been sort of pigeon-holed into one tiny market. I’ve fallen behind in basic computer skills (Excel, QuickBooks, etc) though I know I can brush up on those. 

So here’s my question: Should I tell possible employers at interviews (or even in the cover letter), that I’m looking to change careers or reinvent myself? Does that show a willingness to learn or does it show that I’m starting over?

I’d appreciate any advice you have to give.

Thanks again and best wishes!

Best Regards,
Vivianne L


Hi Vivianne,

Thank you for writing to me!

Yes, cold calling and getting rejections can be soul killing. I started as a telemarketer early in my career and I totally hate it. So I know where you are coming from. 

I know you only asked a direct question, expecting a direct answer (which I will give it to you in a while so please bear with a lengthy email advice) however, I like to throw some of my thoughts in your direction. 

First of all, you are right in saying that you can upgrade your computer skills and perhaps some other skills to repackage yourself to be more attractive in the employment market. So you are definitely in the right mindset here. 

Secondly, I like to ask if you have explored other work from home opportunities out there. If you enjoy freelancing from home, you don’t have to give it up. You can pick up other types of freelancing projects and slowly move away from the inside sale job that you are currently in. You can be a writer (your blog posts are really good) or an editor. You can work on projects to train other telemarketers. You can work on standard operating procedures on telemarketing, inside sales or customer service, coming up with the dos and don’ts as well as telephony scripts for clients. There are plenty of other freelancing jobs out there that will gain from your experience in inside sales. That way you don’t have to drive. 

That being said, I like to highlight my third point. Yes, you might not see the prospect of being a freelancer because there are no promotions, pay raise, huddling of colleagues or even a pat on the back by your manager. I have mentioned in some of my freelancing articles that freelancing and entrepreneurship is a lonely road. However, you can create opportunities for yourself. Instead of working like an employee for your company, turn it around and offer to work as a contractor for them. Offer to hire and train other freelancing telemarketers. Your boss hires you and pays you directly, you manage and pay your employees who do the cold calling for them. In other words, you are no longer just a freelancer, you transit being an entrepreneur. 

My fourth point, which is to give you the direct answer to your question: Should I tell possible employers at interviews (or even in the cover letter), that I’m looking to change careers or reinvent myself? Does that show a willingness to learn or does it show that I’m starting over? 

I am an opportunist. So to reinvent yourself totally is not impossible but it takes time. Like I have highlighted in my second point, you can use your experience as an inside sales representative and propel yourself into related but different positions like a trainer, a Quality Assurance Analyst (where you QA through call records) or even a manager managing a new inside sales team. 

You’ll learn new things and have new challenges yet still be comfortable because it is in the field you are used to. This will be a quicker path to a wonderful new career because of your base experience and your willingness to take up new challenges. That is the best solution in your situation where you don’t have to put yourself through from scratch. 

This way you don’t have the dilemma of telling your future employers that you are reinventing yourself instead you are improving yourself. It is like adding new components to your base machine so that you will be a much more powerful robot. So instead of Lisa the Cold Calling Machine, Lisa became the Inside Sales Expert / Trainer / Recruiter / QA / Manager. 

Even if you feel a compelling need to let your future employers know you are reinventing yourself, don’t list it in your resume or cover letter. The hiring or interviewing manager does not qualify your resume, only the HR does that. If you want, you can tell them during the face to face interview. By revealing that you are reinventing yourself, you are opening a can of questions that you cannot address enough on paper, best to address those questions in presence. 

Finally, thank you for your unwavering support in MiddleMe. 

I do hope that I have addressed your question and maybe throw some light towards your way. If you need more guidance, please feel free to ask for it! 

Please do take care and best of luck in pursuing your dream job.


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13 replies on “A Word Of Advice: Reinventing Yourself

  1. I read your post. Are you a mother? I worked 18 years as a Retail Associate/Cashier. So I feel for you. I’m currently unemployed and casually looking. Good Luck. You look young from your picture.

    Liked by 1 person

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