How Women Can Make BIG Career Changes: 5 Must Do’s from a Pro


I have changed careers several times in my life, from teaching, to non-profit, to high-growth technology, and now to banking. Throughout all of my transitions, I searched online for advice on how women can successfully make career transitions, but found only information lacking a step by step process.

There are ample posts targeted for millennial women on how to get an entry level position, but not a lot of the content focuses on how women can transition careers when they are no longer entry level, but not yet in an executive corner office.


For women who are turning thirty-five, most of life’s deepest questions have been answered. By that point, you may have found your Mr. or Mrs. Right and have walked down the aisle or committed to a long-term partnership. You probably have or are thinking about having kids versus deciding on raising a rambunctious puppy.

If you are a woman making a career transition in your mid-twenties, the decision is likely a solo decision. At age thirty-five, it is a whole different ball game. At this stage of your life and career, you most likely will want to include your partner’s thoughts when making any career decisions which is both scary and exciting.

Making a career transition for any woman will take work. Looking back on my career journey here are some tips that changed the trajectory of my career path.

Know What You Want

The road to a kick ass career is paved with soul-searching, tears, breathing exercises and power poses
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All the experts will tell you to seek clarity, but what exactly does clarity really mean? 

Clarity starts with self-assessment.

Personally, finding the type of work I’m most passionate about and defining my optimal work habits, brought me ton of clarity. Be crystal clear on what your strengths and weaknesses are. In order to do this, approach your career as if you are a detective. Here are my suggestions:

  • Scan over all your prior performance reviews

  • Seek out former bosses and coworkers for insights

  • Scan and study the main projects you managed that succeeded and those that didn’t

Ladies – it’s time to take control over you career trajectory.  Start from a place of clarity. Gathering intel is your first step.

Explore Interesting Job Titles

Once you have intel on your strengths you can research job titles and compare against different sites like Glassdoor, LinkedIn and Indeed. Find the job title that sounds like it matches your interests. Review the description to see if you would like to do the type of work the job requires.

NOTE: Do not read the job description and automatically think I don’t have these qualifications. You’ll never create your ideal career if you disqualify yourself right off the bat. Men never disqualify themselves from roles that might be out of their reach.


Kayne Says No

To repeat, review the job description to see if you would like the work that it entails.

Incidentally, this process helped me discover that Organizational Development (OD) was the right role for me.  Prior to researching that job title, I did not know that OD existed as I was coming from a small company.

Once you have a few interesting job titles, put them into an excel spreadsheet or jot them down. Half of the effort with any career transition is getting organized with the information you are gathering.

Investigate Unique Companies

Next you will want to research companies that sound interesting. Stumped on where to begin?

Take time to think about what is most important to you; reflect on your deepest core values. Try to match your core interests to companies that align with what you value most.

If you are like me and one of your deepest core values is education, find organizations that are striving to fight illiteracy.  Alternatively, go and find the companies that are trying to solve interesting problems and go from there.

 If you are still stumped, look at where your friends work.  Do any of those companies sound interesting? If so, jot down what you like about the particular company in order to create your ideal company profile. Your goal is to create a profile of the types of companies (large, small, startup) and the types of industries (tech, banking, government) that interest you the most. From there you can start to narrow in on the ideal company


Research the Company Culture

If you find a job title that sounds like a good fit at a company that is doing interesting work and aligns with what you value, your next career transition move is to research the company culture. This is the most difficult part of any career change.

Researching culture is very difficult because it is intangible. Your best bet is to talk to as many people who are either doing the work that you want to do at that company OR reach out to former employees to ask about culture. You will never know what’s it’s really like to work at a company unless you reach out and humbly ask. Women need to help each other in this regard. If you receive a note respond with honest feedback. You do not need everyone to respond; you just need a few people to give you a sense of the climate.

Start Talking and Make Human Contact!

Talk to real people who have the job you want

Any woman who has switched careers has done so with the help of networking. Networking will ensure your career transition happens my personal experience making connections, getting to know people and asking the right questions has made the biggest impact on my career. 

Networking can mean different things to different people. For extroverted women, going to big networking events, chatting with a ton of new people is thrilling. For the introverted ladies, (myself included) big events can be frightening and intimidating. Luckily networking does not have to mean big crowds. You can start by asking friends out; then you to talk about your career transition.  These low stakes coffee meetings with girlfriends gives you an opportunity to start sharing your story in a safe environment. Most importantly you have to get in the habit of reaching out and asking – women must make the ask. Increase your confidence by asking friends out then you can branch out to reaching out to strangers. 

There is a special place in hell for women who don’t help other women
— - Madeline Albright

Keep in mind that not everyone you ask is going to say yes, in fact, you will get ignored by many people - get comfortable with feelings of rejection. Show the person you are asking why they are important to you (even if they are strangers). Humbly make the ask and be prepared for rejection.

Rejection is easier to take when you do not have all of your networking eggs in one basket. Make yourself a schedule. If you want to have 1-2 coffee meetings per week, you’ll need to reach out to 10-15 people at least! Why so many? Some people will be on vacation, some people will not be able to meet for a few weeks, some people will ignore you. The more people you reach out to the more chances you have to make the 1-2 coffee commitment.

Write emails to total strangers. In my own experience I landed my last two roles NOT through people I know,  but because I sent emails to total strangers. In my subsequent posts I'll show you how to craft emails that get read!

LinkedIn is helpful but only to a degree. You can easily waste and entire day searching at job titles and job descriptions only to find that you didn’t do anything productive. You need to utilize LinkedIN as a research tool but after that you need to spend the majority of your time, researching people to out to and sending the email.

90% of your time should be connecting in some way (phone, coffee, breakfast, Skype) and 10% can be spent on LinkedIn looking for roles.

How to Allocate Time .png

90% of your time should be connecting in some way (phone, coffee, breakfast, Skype).

If you want to make that major career breakthrough you will have to leave your laptop and meet people in real life. More than likely your next role will come from connecting with someone you don’t yet know. Initiate human contact.

If career transitions were easy, more women would be doing. The right role at the right company with the right culture at the right salary is out there for you, but you have to do some work to get there. These tips should help you on your journey to your next career transition.

If this resonated with you leave a comment below!



Interviewing Preparation Requires Critical Thinking: 5 books to read before any job interview

I have a few different Goodreads shelves and one is titled “Thinking” where I collect the best books on all things – critical thinking, learning, and decision making.


One of the biggest competitive advantages you can leverage in your career or business is the ability to think critically and make better, faster decisions. If there is one thing I want to focus my time and energy on and go ‘all in on’ it’s making better decisions.

If you can get even 2% better at decision making you will drastically increase your results. I try to focus my energy on hacking learning to find the strategies and techniques that work for me.

When faced with a job interview you will also need to be able to think critically in the moment to show a prospective boss how you would approach a problem. If you want to get better at interviewing, then you’ll want to focus your time at getting better at thinking critically.

The 5 best books on critical thinking to prepare you for a job interview:

1)      “How To Read A Book” by Mortimer Adler & Charles Van Doren


Adler & Van Doren penned the classic text on how to read a book. Touted as “the best and most successful guide to reading comprehension for the general reader” - this one is a keeper. The most important part of the book is the detailed approach to reading different types of material which requires different reading techniques like skimming, inspectional reading and extraction. The book reinforces the notion that you can’t approach reading in the same way with every book because one size doesn’t fit all when it comes to learning. The same is true for interviewing, you must make sure you are customizing your language and how you approach an interview based on the unique needs of the company you are interviewing with.

2)      “The Art of Thinking Clearly” by Rolf Dobelli


“Art of Thinking Clearly” is a quintessential read for anyone with important decisions to make which means it’s applicable to everyone on planet earth. I loved the section where Dobelli explores the question “Have you ever invested time in something that, with hindsight, just wasn’t worth it?” We all have wasted time on Instagram and Facebook, but what about the weeks, months, and years wasted in a job that wasn’t right for us or at a company that didn’t align with our values. Dobelli’s techniques will help you pull yourself out of the rat race. For a companion book on this topic, check out Essentialism.

3)      “Mindshift” by Barbara Oakley


Oakley’s book does a deep dive into how you can change your approach to learning and bring about surprising results in academics and in your career. She delves into the neuroscience of how the brain changes when you learn different skills. If you want to go deeper into the neuroscience, Cal Newport’s Deep Work is a great comparison book to show you what happens to your synapses when they are fired. The last few chapters focuses specifically on MOOC’s – how to study and learn for a completely digital courses. I have yet to see any other author getting this detailed on how to approach learning in the digital age. It’s no wonder Oakley’s MOOC Learning How To Learn is one of the most popular MOOC’s of all time – that’s a lot of MOOC’s for one sentence.

4) “Learn Better” by Ulrich Boser


Boser had me at his job title which is “education researcher” what’s cooler than that? The geek (and former teacher) in me is profoundly jealous he gets to put that on his resume. Learn Better spends more time than the rest of the books showing us that how we learn is just as important as what we learn. When interviewing for your next dream job, you must first spend a lot of time learning about the company to make sure it’s a good fit for what you are looking for. Boser guides you through ways to learn better and you can apply them to interviewing.

1)      “Thinking in Bets” by Annie Duke


Interviewing for a job is all about making decisions when you don’t have all the facts and when there is a lot of uncertainty. You don’t know if you’ll like your boss or coworkers and you don’t understand what the company culture looks like. Duke provides the reader with tools that you can use to approach decision making in a way that allows you to be less reactive and ultimately have more success over the long run. We can all stand to be less reactive in accepting job offers at companies that don’t align with our core values.

Have you read any of these picks? Let me know by leaving a comment below.


DisruptHR Video Tear Down

What’s more uncomfortable than getting up on stage and presenting to 300 strangers… watching the replay! I’ve held off on writing this post because I hate seeing myself on film, absolutely hate it.  I don’t like hearing my voice on film or through headphones because I sound alien. I also don’t want to watch the video because I can’t remember if I messed up or embarrassed myself so why go there, right?

Wrong. Top performers in any industry routinely practice their craft and create feedback loops to continuously improve performance (for more on this check out Deep Work or Peak, or anything written by Ramit Sethi). If you want to improve performance, you must find ways to review your performance in real time, which reminds me of a time when I was little…

I remember sitting on the floor in my living watching video footage of my mom’s students reciting speeches in front of a camera. Mom was a Communications Professor at a local community college and one of the assignments she gave her students was to prepare a speech on camera so that she can provide feedback. I remember popping in the VHS while mom sat there with notebook in hand to jot down her thoughts. She’d critique what she thought her students did well and what they could have done better, and I’d stay for the popcorn. Did I forget to mention that I was around six or second years old when we started this tradition.

Mom was also in charge of preparing the valedictorian speaker for each graduation season so each summer a graduating senior would arrive at our door scared as a mouse in desperate need of mom’s help. Mom set up a makeshift podium on our kitchen table and they’d practice while I listened from the other room trying to anticipate the things I thought my mom would comment on. Oh the memories! I learned a lot from being a spectator and now I know what to look for when reviewing my own film footage.

My DisruptHR video is up and I’ve had some distance from the event, now is the perfect time to watch and do my own teardown of what went well and what makes me cringe. What’s a tear down without a little help from mom, I’ll share her tear-down thoughts as well.

As they say in football, “let’s go to the videotape!”

The Goods:

Overall, my enunciation was good, I brought a lot of high energy to my speech and I think that came through. I look as if I’m having a casual conversation with a friend and I look and feel authentic

  • I don’t look nervous and I didn’t feel nervous when I was up there so I’m smiling as I write this because all the preparation (20 + hours, more on that here and here ) paid off!
  • My timing is spot on, I don’t feel like I’m rushing through slides
  • 1:15 – I quickly glanced down at the teleprompter and noticed that the slide is missing a key image that should be there, the image sets up the rest of the speech so I’m a little jarred. I briefly make a comment “Hmm, something is missing there” and make a joke of it rather than stopping my entire grove and got a laugh from the audience which was a big plus. However, I pointed directly at the teleprompter – I doubt the audience would have known had I not pointed it out. Note to self – don’t point at the teleprompter.
  • 3:15 – I use the phrase “take an inventory or an audit” which I adlibbed as a way to tie my content back to an early speaker – this got a laugh and made me feel like I thought quickly on my feet and way “in the moment.”

The Cringe Worthy:

  • Mom and I both agree that I look like I am playing a tennis match moving back and forth on the stage, pointing and shooting.
  • I look awkward pacing back and forth and it looks unnatural. Even during my practice sessions, I really had difficulty with the physicality of giving a speech. I need to work even more on this for next time
  • Mama Dukes did not like my outfit!!! She felt that I had too many shades of blue, she may have a point. Looking back my outfit choice may not have been the best, but I purposely picked an outfit that I felt both strong and confident in so at least it got the job done.
  • My title and the topic of my speech didn’t align - for next time I’d like to write a snazzier title that better aligns to my content

So, there you have it, re-watching the five-minute presentation wasn’t easy, but I learned key takeaways and useful insights to implement for my next presentation. On a plus note, on whim I applied for and sent in my video to a call for speakers for the City of Detroit. They loved my vulnerability in my video and have added me to their speaker line up, we are trying to set up speaking engagement for late September.

Preparing for DisruptHR - Part 2

Now that my Presentation deck is complete (read more here) I’ve spent the past three weeks practicing and my practice has morphed over time. To give you a sense of what I mean. My approach below in somewhat chronological order:

3 Weeks Out - 

Learn Your Word Count

When sketching my content, I had a sense of what I wanted to say for a few key slides, but for others I had to start from scratch. The first thing I did was to figure out my word count which for a 5-minute speech is somewhere between 625-725 words depending on how fast you speak, I’m on the slow slide. Then I took Seth Godin’s advice, if you must prepare a 5-minute speech opt for a four-minute speech instead because less is always more. My total word count is below 600 words.

Seth Godin.PNG

Similar to my advice in Part 1, I found that writing out my words in a Word Doc rather than the notes section in PowerPoint really helped me to shape the structure of the talk.  Each mini paragraph represents a slide and about 15 seconds of speaking. 

I probably edited my script easily 20-25 times, so I worked a little bit on it each day for about a week. Once I had most of the script written out I started to practice reading off my script and timing myself on my cellphone. I did this alone as I’m not yet ready to unveil.


2 Weeks Out - 

Stop editing!

The perfectionist in me could continue to edit the script, but I had to step away from my laptop to give myself enough time to start practicing in full. I spent a few days practicing the entire speech in full by reading off the script. I probably did a total of 30 run-throughs. I practiced with the slides advancing every 15 seconds and timing on my cellphone so I could get a feel for when to pause and when I had too many words per slide. Still alone, still not ready to unveil and getting more and more nervous about the fact that sooner or later I’m going to have to practice this in front of people.



1 Week Out - 

Gain an Audience

It’s time to take the training wheels off and actually practice in front of someone so in this case it is best to practice in front of someone you trust, I opted for my spouse and 5lb Yorkshire Terrier Lenny {INSERT PIC OF LENNY). At this point, I’m still reading off my script, but I’ve practiced enough where I have memorized some of the slides on my own. I’m noticing that I’ve practiced full through so many times that the first 5 slides are much easier for me then the back half. I now need to focus more from the middle of the speech to the end.


4 Days Out (At Least)

Blind Practice

This is the most difficult part of practice. The first time I practiced without the slides or my script in front of me I completely choked – it did not matter that I had practiced for weeks at this point, I literally could not remember anything; I completely froze. Good thing I still have a few days before the big event. I put the heels that I plan on wearing on and put my script away. My spouse could view my slides, but I couldn’t so I literally went at the blind, as the slides advanced I would get a quick queue. This is the best way to practice. I often forgot what slide comes next and had to make stuff up. At times, I literally let 15 seconds slip by until the next slide appeared so I could regain my composure. Having my dog Lenny there was also helpful she started playing with a chew toy that made a lot of noise, but I had to just keep moving. The room will have 300 people with a ton of noise so I need to be ready.

I’ll post Part 3 as a follow that will detail how it went in the hopes that I didn’t bumble anything.

Preparing for DisruptHR [Part 1]

I’ve spent the last two months thinking about my upcoming presentation for Disrupt HR Chicago where I and 10 other speakers will have a chance to speak on a disruptive HR related topic. Speakers have  a total of 5 minutes on to speak on a topic with a total of  20 slides, slides advance every 15 seconds automatically. This is a rapid-fire type talk with an audience of about 300 people. My final slides were due yesterday and there were many steps along the way to get to completion.

I started with a general sketch of what I want to talk about. I also know how I’d like the audience to feel when I’m finished, and I know the important takeaways, the a-ha moments.  In thinking about my approach to my talk I’ve noticed a few ideas that have helped me start to craft my presentation:

Sketch ideas on paper first

Revolutionary idea here folks. I made the mistake of starting to design my talk in PowerPoint first and found that having to design a presentation from a blank slide is scary. I never realized how much starting with a logo helps to get the creative juices flowing so without them I felt lost. The idea to start by writing out our ideas on paper first echo’s what Garr Reynolds from Presentation Zen writes about. I received similar advice from DisruptHR Chicago Co-Founder Nicole Dessain. Nicole added that when sketching out your ideas on paper add a short theme to each slide and draw an image that could fit for what you want to convey. Below are my 20 slides with theme on each slide – this is where I started. I chose to sketch using a Sharpie Marker to focus on ideas rather than getting all the words down. As Gary Vaynerchucnk would say… “Now is not the time to get fancy”.




Mash Two Ideas Together

Each speaker is fortunate enough to have a call with an expert in storytelling  and I was lucky enough to connect with Beth Nyland from StoryStudio Chicago. When I talked to Beth I had a dilemma, I wanted to talk about three topics and wasn’t sure how I could fit all three into 5 minutes without sounding disjointed. She asked questions that made me rethink my approach. Beth asked “Have you thought about mashing two of the three ideas together?”. I obviously hadn’t thought of that and once she said it my entire presentation started to click. She showed me ways I could take two of the three topics and mash them together in a way where I would be able to connect all three. The mashing technique allows me to have a coherent talk and showed me a different way to convey my ideas.

Thoughtfulness Takes Time

Five minutes is not that long to convey a message that has meaning and will make an impact on the audience. 15 seconds per slide is barely anytime so every single word needs to really count when you only have about 600 words to use.  I’m glad I’ve given myself the two months to let my thoughts and ideas marinate and wander. Some ideas have lasted while others no longer make sense for what I want to talk about. The “think time” has been invaluable to craft and shape my message.

I’ll post Part 2 as a follow that will detail how I practice my speech.