9 Common Mistakes Most Women Make When Re-entering the Workforce (and How to Avoid Them)

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So, you’re trying to get back into the workforce after staying at home with your kids, or maybe after a divorce… but you probably have some concerns about the challenges involved. And that’s okay! 

My name is Diane Prince, and after owning a staffing agency for over 15 years, I’ve seen it all. The good news is that, even though landing a good job takes hard work and dedication, it’s actually quite simple and formulaic. And I’m here to make it easier for you. 

By avoiding these 9 common mistakes most women make when re-entering the workforce, it still won’t be easy, but you’ll be taken a lot more seriously in your journey. Whether you are struggling for cash, or you simply need to rediscover your self-esteem, you’ll have a better chance at getting your foot back in the door – and affording that spa pedicure that you so badly need!

1. Don’t over-explain the gap in your resume. 

This one is super annoying. Your future boss wants to know how you can fix their problems and what you’ll bring to the job. Sure, you can quickly explain that you stayed home with kids. That’s fine. But then move on to what you have to offer. Use the job description as a guide and have specific examples of how you’ll be amazing in the role.

For example, if the role involves planning events, tell about the time you had to attract volunteers to attend a meeting during a stormy winter day, so you put together a fun last-minute summer theme with drink umbrellas and all. Your future boss wants to see you as a fast-thinker and problem solver, and guess what? They’re not going to fact check your answer. 

So, go ahead and Google common problems and solutions that are relevant to your potential job. Yes, I said it, you can embellish! After all, you want to show how you can think on your feet!  

2. Don’t volunteer in the wrong places. 

I’m sorry, Mama, but you’re going to need to prioritize here. Where are you spending your time and with whom? If you’ve been staying at home, going back to work is going to require a major shift in your priorities. If you’re using your precious hours on a committee with stay-at-home parents who are also out of the workforce, you’ll need to decide what’s more important – making friends or getting a job. I’m not saying that friendships aren’t important – they are! But, just for right now, volunteer in places where future employers might be.

For example, local entrepreneur pitch competitions would be a fantastic starting place. There, you can meet out-of-the-box thinkers who would be more likely to hire an alternative job seeker. While startups don’t have a lot of money, you can get back into the work force by working at one. And you can gain a ton of useful skills.

Pitch competition attendees also include sponsors (bigger companies, law firms, marketing agencies) as well as equity and venture capital professionals. Find these at Meetup.com, then contact the organizer to find out what kind of help they need. Have personal business cards printed with your name, email, and phone number too. This way, you’re on-the-ready when you meet interesting people. And, yes, believe it or not, people do still exchange business cards!

3. Don’t forget to master basic tech skills.

If your interview is remote and on video, you need to practice long before call time. Don’t be fumbling to download Zoom at the last minute or looking to remember your Skype password. Make sure you know, in advance, which platform the interviewer is using – there are a lot – and practice with a friend. Have a reasonable email address that doesn’t include information about your spouse or your kids.

For example, jacksmom@gmail.com or malibuwife@yahoo.com are both going to make you seem as a wife or mom. Although that’s okay in your personal life, you might not be taken seriously as a professional individual. Actually, they’re kind of lame in your personal life too, so you may want to re-think if these email addresses resonate with you!

Also, make sure you understand which time zone the interviewer is referring to (Google Calendar will automatically convert to your own time zone). Empty your phone voicemail, so it’s not full as well. Basically, make sure that you appear to be functioning as a real-life person in the business world and not as a frazzled multi-tasking mom who hasn’t used a computer since floppy disks.  

4. Don’t talk about your kids. 

Please don’t mention ANYTHING about your kids, husband, wife, boyfriend, whatever — unless asked. Legally, an employer is not allowed to ask these types of questions, but assume that they will anyways. What should you do then? Answer questions briefly and change the subject back to assuring the interviewer of how you’ll be reliable, on time, and can handle the work in a professional manner.

Even if the employer is a woman who struggles to keep it together because she has her own brood, stay on topic for the job. This includes how you’ll be amazing at it. Your future employer is developing an image in their head of what it’s going to be like to work with you – set the tone.  After all, would you rather give them a mental picture of your running to the ER with your sick son or of your walking in the door bright and early, organized and ready to go?

5. Don’t have an incomplete LinkedIn profile. 

The truth is that you need a complete LinkedIn profile for several reasons. One being that people with complete LinkedIn profiles are 40% more likely to be contacted. Even though you need a resume, your potential employer will look at your LinkedIn page. They may even only look at your LinkedIn instead of your resumé! There are tons of YouTube videos and articles you can check out to set up a complete LinkedIn profile. Simply Google “how to complete LinkedIn profile” and the current year, so you get the most recently created instructions. 

6. Don’t minimize your accomplishments. 

One of my pet peeves is when women diminish their big accomplishments. I used to do this myself, and I would give credit to my former business partners, who were men. But once I started thinking, and acting, like a dude on this one, I’ve been able to wear my accomplishments with pride.

Think of some major bad ass things you’ve done. They can be from your former career. Or they can be from volunteering. They can also anything else that will give your future employer an image of you saving the day. You’ve probably heard this before, but don’t ever say, “I just…”

And don’t ever apologize for things that don’t require apologies! For example, instead of saying, “I’m sorry for not bringing my references with me,” instead say, “I can email them to you by end of day today. Does that work?” Do you see how power shifts in those two statements? 

7. Don’t act desperate. 

I get it… you might BE desperate. I’ve been there! It’s not easy to appear confident when your rent is due next week, but you just spent your last $20 on a bottle of rosé. I’ve had numerous people approach me throughout the years, begging for work. While sometimes, I do have a spot for them, usually I’m afraid that they’ll bail as soon as they earn enough money to pay their overdue bills. Or when something better comes along. It’s like dating: nobody wants to be with someone who is desperate.

Whatever your dire situation, keep that for your close friends, therapist, and your journal. But when you’re out networking or interviewing, have a good story about what you’re doing now (this is one of the reasons I love side-hustles) and do the old “fake it ‘til you make it.” You can get back to worrying later, when you’re at home.  

8. Don’t obsess over one opportunity. 

I see this time and time again. And I too have fallen prey to this irresponsible mistake, obsessing over one possibility. Thinking that you have the job before getting an offer can set you back several days if you’re not still “out there,” interviewing and meeting new people. Once you’ve gone through the interview process and sent a follow-up note within 24 hours, your work is done. So, you need to let it go!

Now,you can, and should, send a follow-up email the next week if you haven’t heard back yet. But, it’s only the right job if they want to hire you! So, no weighing pros and cons of the job, no planning your move across country, no promising the kids a vacation with your new salary. At least, not until you’ve gotten an offer and actually have started the job. Obsessing over one opportunity is a time waster that can derail your job-hunting rhythm. So, interview and move on to the next until you have an offer in-hand.  

9. Don’t job hunt if you’re not ready to return to work. 

If you haven’t been working for several years, you’re going to need to make some giant changes to re-enter the work force. For example, you need to consider childcare, pet care, when and how to fit in doctor appointments, working out, errands, grocery shopping, friends, time with spouse or kids, etc. etc. etc.

While a future employer legally cannot ask you about family responsibilities (they may ask anyway), they can ask if you have any obstacles that would prevent you from being at work during the required time. You’ll need to make a plan and make sacrifices, but they can be worth it to start this new chapter in your life.  


Do all of the above sound super overwhelming and annoying? If so, you might want to consider an alternative way to work. For me, I took a hybrid approach when I didn’t have the wherewithal to start a new business, but I knew I wouldn’t be a good fit for a 9-5 grind. 

First, when my company went out of business, I didn’t think that I was hirable because I’d only worked for myself for 20 years. I volunteered at a pitch competition and was paired to help an entrepreneur. Two months after the competition, I reached out to see if she needed any help. I was hired to create their business-to-business sales channel.

Since I was a contractor, I was free to pursue other opportunities that suited my own interests and my independent spirit. Since then, I’ve been working as a consultant, heading up sales in early-stage companies, while I have time and freedom to create the community around my blog.  

You can find information on my blog about side-hustles that can turn into real money-making businesses. For me, I don’t want to be held to a 9-5 (or more likely 8-6 or later) schedule, I want to go on vacation whenever I want, and I don’t want to set an alarm. 

Does that sound like you too? Then check out my recommendation page for a few ideas and join my private Facebook group to meet up with other women facing similar challenges.  

About the author
Hi, I’m Diane Prince. I’m a serial entrepreneur, speaker, and single mom to three powerful young women. By day you can find me helping early-stage companies build their revenue through sales. And by night and weekend, I’m working to teach women money making strategies that can pave their way to personal and financial freedom. My first entrepreneurial venture kicked off at age 27 when I founded a temp staffing agency with my then husband. We grew the business to $50 million in revenue before selling it to a publicly traded company. By age 33 I found myself in the midst of success most never imagine, living in Malibu, and enjoying a luxurious life. Soon after the sale of our company, however, my husband and I divorced. During that time, I took control of the second business we’d built together. I was able to generate another successful exit and felt confident I could do it a third time. I decided to take a new risk and found Winnie & Kat, a women’s clothing brand which, similar to Stella & Dot, gave women the chance to run their own businesses and generate flexible income. Despite my passion, the company ultimately failed and the risk I’d taken had left me filing for bankruptcy. My life had been turned upside down. Everything I’d once had was now gone - my husband, businesses, Malibu home, social circle, and lifestyle. I doubted that I could ever make money again and feared that I would be stuck in this new life like so many of the women I’d begun to meet whose stories were not so dissimilar from mine. I knew I wanted to be a better example for my daughters and show them that being a single mom did not mean that I had to be broke. So, I leaned into my natural resourcefulness and committed to finding ways not just to save, but to make really good money. I taught myself how to earn income from affiliate marketing and blogging and even became a top recruiter for a direct sales company. By challenging myself to think differently I discovered that there are endless opportunities to pave your own way, earn a great income, and live your best life. Today, I can proudly say that I’ve worked my way back, this time on my own, and live once again in Malibu. This personal experience has taught me that it’s not only possible to reinvent yourself but that “losing it all” can really be an exciting opportunity to create a new and exciting life. Many of the women who I’ve met on my journey have asked me to teach them what I’ve learned. Their requests and the stories shared by so many others have fueled my mission to change the narrative for single mothers. I hope to use my platform to help other women find their own ways to do bold things and live life to their fullest potential.

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