career pivot
Making a successful career pivot is about creating connections based on what you already know about yourself, where you are in your life, and where you want to be in your career.

Sound like a process?

It is.

But, it doesn't have to be a complicated one!

Many people find a sticky point before they are even able to start to take action on their new career journey.

So many of us hold ourselves back from the next steps to our career change because of our fears of failure, lack of confidence, and just waiting to have all the time in the world for things to change. 

But, things don't just change.

And, they won't change on their own.

Don't let you own self-sabotaging ways get in the way of making those career moves.

Jenny Blake, a career and business strategist, international speaker, and the author of the books, PIVOT: The Only Move That Matters is Your Next One and Life After College, shares strategies for those moving through their career change process and even those that are just beginning to evaluate where they are in their particular situation.

When you find yourself stuck, take a deep breath and follow the process below to regain your career pivot perspective.


#1: Focus on Yourself


The process of your career change is intense and can take you into a place of deep overwhelm, where you may even be so focused you begin down one path and develop tunnel-vision until you get to a result (even if it’s not truly the results you’ve mapped out for yourself).

You may become so invested in making the change that you lose sight of your overall career and life goals.

So, take a moment or two…or three… to step back regain your perspective on what matters to you. What you value and what you really want out of your next career.

Ask yourself the following questions:

  • Who am I? What do I like to do? What don’t I like to do?
  • What does success look like for you?
  • How much you want to be making?
  • What time do I want to wake up every day?
  • What types of people do I want to surround myself with?

Be as detailed as you can be when you create this Ideal Day Map.

The more detailed you can get with your ideal day, the better you can focus your energy to actualizing this vision.


#2: Scan for People, Skills, & Projects


Once you map out the vision of your ideal day, begin the scanning process.



Think of who you can connect with that is either in the same place as you – looking to make a change, someone that is already in the industry or organization that you would like to work, or someone that knows someone that can offer you advice, help, or provide you with an ‘in’ into the next stepping stone of your career.

You can also look into starting a ‘friendtor’ relationship with one of your like-minded friends for accountability and support during your career transition. ‘Friendtors’ have the capacity to be so valuable to your career journey. It’s another place where people put pressure to find a mentor, but staying accountable with your friends can go a long way.



Do you know how you want to grow?

If you are at a pivot point in your career, you have room to grow which is more than exciting.

If there is one thing about the majority of successful career changers, they have a huge capacity to learn. They enjoy growing by conquering their challenges.

So, ask yourself, where do you want to grow? What skills do you want to improve on?



After you scan your skills, think about and look for tiny micro-experiments to dip your toe into a potential career.

This could be anything from volunteering your knowledge and skills to test out a type of job or getting an internship to get a feel for what it would be like to work for a particular organization.

#3: Make Yourself Discoverable


Network. Network. Network.

The goal is to let people know that you’re looking for a new career and what type of job and industry you’re looking to work in. So, be intentional and put yourself out there.

Whether you send emails out to your friends, family, and colleagues, or start your own website to promote yourself, you need to take the initiative to demonstrate your skills in a public way.

If you don’t know what to say, we’ve provided sample emails below for you to use as a template to get your networking emails started.

Here is a sample of an email you can send if you are looking to switch up your career:

If you own your own business and are looking to expand outside of what you know, send an email similar to this one:


Follow this 3-step framework and stop holding yourself back from your next career opportunity.

Be more intentional with your career pivot and push past your sticky points to successfully move forward with your career transition.

Career change is difficult stuff. That is why we've created the Career Change Bootcamp program that was created to guide you to build a strong foundation that will go even more in depth to help you determine what it is you want out of your next career.

Read more about it here or visit our Career Coaching resource for a more personalized one-on-one career advisor.

Transcript from Episode
Scott Barlow: Welcome back to Happen to Your Career. I am so very ecstatic to be here with a special guest. Somebody who I have been bouncing around similar space and careers for a while. So many people have said we need to meet. Today is the day. We finally get to meet and have a conversation. Welcome to Happen to Your Career Jenny Blake. How are you?

Jenny Blake: Thank you Scott. It’s an honor to be here. I’m also so glad we finally get to connect.

Scott Barlow: Perfect. I couldn’t help myself, so I’ve got lots of questions. I’m fascinated by people’s stories and you have a unique one. I know we will dive into that but also we are going to talk about how people can successfully make a pivot and share your expertise. But before we start how do you describe what you do?

Jenny Blake: I primarily say I’m an author. I wrote a book called Pivot and I do coaching, speaking, and consulting related to that. I realize that what I really love are big ideas and simplifying complex topics like change and what is next. From those big ideas comes everything I do and what I do to earn a living. One of my favorites is keynote speaking. I love it more than the process of writing of book. Of course I like having written a book and letting that be the platform.

Scott Barlow: I’ve talked to so many authors and we have a lot of books we’ve shared with our audience but haven’t went the publishing route, but plan on it over the next year and a half. I’ve been asking authors and get the same response. They say I love having written a book. That apparently seems to be the common theme.

Jenny Blake: Although I’ve been writing my whole life I don’t identify as a writer. It doesn’t come easy to me. Even marketing Pivot. I loved being on a podcast but when it came to writing an article even for a prestigious site I would procrastinate and felt too spent from working on the book. My friend Dory Clark can turn out three to four articles a week no problem.

Scott Barlow: I’m more on your side of the fence than Dory’s. I have friends that think it’s no big deal. I’m super curious because you haven’t always been keynote speaking, marketing new programs, and helping people in a variety of ways, so where did it start for you?

Jenny Blake: Interestingly enough, when you say I haven’t always, even as a kid I made my brother play school. Whatever I was learning in school I would make worksheets for him instead of playing house or any imaginary game we would play school or business. He is two and half years younger. Even in those early days I liked learning and understanding something and teaching it. In the business I loved creating things. I started a family newspaper when I was ten and continued it all through high school. It was the Monthly Dig up. Even there I loved seeing what was out there, curating information, stories and technology trends. I charged money. I think subscriptions were five dollars to cover printing and postage. That was my early form of blogging before it was a thing.

Scott Barlow: Were people outside the family reading this too?

Jenny Blake: Extended family and friends. Cousins, uncles, godparents, parent’s friends. It was about fifty people for the subscriber reach when it was done. It was really fun.

Scott Barlow: What happened from there post high school? Where did that lead you?

Jenny Blake: I thought I was going to be a journalist. In high school I was the California Journalist of the Year. Top four finalists in the country. And my first pivot in life was being rejected from every journalism program that I applied to. I didn’t know it was a pivot at the time but I thought what on earth? I had been planning to do this. I was the editor and chief of my high school newspaper. What do you mean I just got rejected from Columbia, Tufts, and Northwestern. I ended up getting into UCLA which I was excited about even though I planned to go to school on the east coast. I wrote for the Daily Bruin for a year then I realized maybe I could broaden my horizons beyond journalism. Deadlines were stressful, everyone on the staff had failing grades and were exhausted and burnt out. It wasn’t nourishing. I had to say no to that. It was hard because it was closely tied to my identity. I started studying political science which got me my first job at a startup with my professor while I was still a student. Everything happened from there. Blogging and writing the books brings back my skills in a different way.

Scott Barlow: I notice recurring themes and patterns. You went to the startup and it got you that job but there were other things you could do. Why did you take that?

Jenny Blake: The opportunity came to me my junior year. I wasn’t looking for fulltime jobs yet. I had interned at Rock the Vote which I enjoyed tremendously. I hadn’t been looking and this fell out of the sky and was in my home town. I decided it was now or never. I took a leave of absence from school. Why not be the first employee? I can stay at my mom’s while I get it figured out. I moved home. My friends were like what are you thinking? You have sixty years to work so why cut your college experience short. I learned so much. I later went back and graduated with my class because I was ahead in school. The startup was so fun. I was employee one and helped and watched it grow to thirty people. I got to wear five hats – marketing director, webmaster, office manager. That set the foundation for why I started Life After College, the website and book. I wanted to help other twenty somethings that were as lost as I was. I entered the working world before any of my friends and didn’t know what it was about, what to wear, or how to pick a health care plan. There was so much that confused me.

Scott Barlow: All the decisions that go along with “life after college”.

Jenny Blake: My first tagline was “no one said it was easy.” I realized it might be pessimistic so I changed it to “wake up, live big, love the journey.”

Scott Barlow: I was going to ask what ones didn’t work out prior to “life after college”. Where does Google fit into all of this?

Jenny Blake: After two years at the startup I felt like I was hitting a plateau and I was too young to know how to talk about that to the founder. My first and last career conversation was me giving my two weeks’ notice. I regret that. To this day my work is dedicated to helping people have career conversations. I had been managing our Google AdWords accounts at the startup which pivoted to being an AdWords Product trainer at Google. I trained over 1,000 people my first year there. It had my long-term goal in mind of being an author and speaker someday. I used to get bright red when speaking in front of a group but I knew this job would help set me up for what I wanted to do later.

Scott Barlow: How did you identify that was what you wanted to do later on?

Jenny Blake: It wasn’t a question. It was more about when could I be an author. I thought maybe in my 50s. What does a twenty something have to say about anything? The Life After College idea felt within my grasp. I was assembling tips, quotes, and suggestions getting all the wisdom out there and breaking it down. I saw myself as a curator not an expert at the age of 25. I always, even as a kid, loved creating things. I don’t know who I first saw to be a keynote speaker. It wasn’t Tony Robbins but I was reading a lot of self-development stuff. Even Dan Pink was one of the first I saw and the authors that came to Google. But it was before I went to Google that I had the urge. I can’t say, I’ve just been very clear. Especially since I left Google six years ago I haven’t looked back. I had a hunch I would want this full time. There hasn’t been a second that I regretted it, even though l loved my time.

Scott Barlow: That is so interesting in a variety of ways. I heard that you clearly identified some pieces even early on on what you wanted to do and it became more a case of how to make it a real possibility. Stair step type of events happened. One thing led to another and all of a sudden, I’m making the assumption you aren’t 50…

Jenny Blake: True, I’m 33.

Scott Barlow: You thought some of it would happen at 50 but clearly it didn’t.

Jenny Blake: I think we are waiting for permission for someone to say you are qualified now. Even when I set up the “Life After College” website in 2005 and started blogging in 2007. I remember the fear of who am I to put my ideas out there and raise my hand with something to say. But who are we waiting for and why? Of course getting an advance degree or more experience is a good thing, things like coach training school, but at the same time how can you start where you are and silence the voices saying you aren’t good enough, not ready, you’re too young or old. We are all going to hear them when we are doing something significant but the key is to keep going.

Scott Barlow: Let’s talk about that then. One of the questions we get emailed constantly has to do with this. It’s that I think I want to do this thing, like writing, or move into environmental, or I know I want to but I don’t consider it a real possibility. What I’ve taken from like a thousand of those emails is we are waiting for permission or don’t see how it could be possible.

Jenny Blake: It’s hard to see. I say we live in a nonlinear universe. Anything can happen at any time. Anytime you say only if then, or only when this happens I can do xyz. I always stop and question it. It can be true but most of the time there are ways around it or ways to start a smaller version of it. Anytime we put a limitation like I don’t think that is possible.

I’m living with and dating a painter. He is a fulltime painter. Most people say you can’t earn a living that way. And it is true there are a lot of starving artists out there, but why does it have to be you? If you put intention behind it and strategy. I believe everyone has a different soul blueprint and path, just because you want it doesn’t mean you will be Jeff Koons and make a zillion dollars either. But why listen just because society or some outdated concept says you can’t do it?

Scott Barlow: I almost feel like, and I have no idea where this is going to take us, but I feel like when you get to that situation you described and you are saying if I only had….the four year degree, the time, etc. Having that be a trigger point for you to stop and say there is another way to do this, I love that concept. From there, if that is something you want I feel like it’s an obligation to yourself to explore that in one way shape or form. Otherwise that borderlines into knowing you are setting yourself up for regrets. I can’t for myself fathom going down a road where you are setting yourself up for regrets.

Jenny Blake: Right. I talk in my book about how growth individuals, people listening to a show like yours. We don’t have FOMO we have FONT – fear of not trying. The biggest regret would be not trying. That is selling ourselves short before we have a chance. I don’t know about you but I would rather try and fail and keep going knowing I tried. Failure stings and isn’t fun especially if money is associated and you lose it, but so what. At least you know you tried. Not taking any steps toward your calling can become soul crushing.

Scott Barlow: Let’s talk about what people can do about that. In your book you describe some actual strategies to move through this process but also for people starting in that place where they already have an inclination or clue or something to hold onto and are evaluating it from an if I only had this then I could do that situation. What can they do to go from that space to be able to begin making it happen?

Jenny Blake: This is where I got stuck. I left Google. I was a year and a half in my own business. I had become known as the girl who left Google and the girl who left college. Everything I talked about was leaving things which wasn’t inspiring. I began wondering who am I, what’s next, how can I have an impact, and what can I build a meaningful body of work around? I really struggled. What kept me struggling, which made my bank account balance dwindle to zero, was focusing so much on what I didn’t know, what I didn’t have and what I didn’t want. It wasn’t until I had to solve the question or go get another job or leave New York that I realized it.

An analogy of a basketball player came to me – when the player stops dribbling they plant one foot, which is their source of strength, stability and foundation, they can scan for passing options with their pivot foot. For someone who is scanning and getting discouraged on what they can’t do and what isn’t going to work, I encourage you to go back to the plant foot and see what is already working. What am I already great at, in what small tiny way am I already doing this. What does success look like? If I were to attempt this where do I want to end up in a year? It can be really inspiring and motivating to push through some of the fear.

From that place look for related things. Don’t stretch too far. As much as I used to adopt the model “take great leaps,” now I am more pragmatic, especially when I’m the one paying the bill. It’s about connecting based on what you already know and where you are. What are small experiments you can run? Tiny ones, take the pressure off to get the answer. If you want to write a book, write for fifteen minutes a day or a week. There is no reason to wait until you have all the time in the world and financial resources. I think a lot of people think if I didn’t have this stupid day job then I could do a trillion things. The constraints a day job puts, while footing the bill, and while incubating the side project is quite valuable. Those creative constraints on time are helpful. The times I’ve went to a week-long romantic sounding retreat in the woods to write I don’t even flick open the computer. I’m paralyzed by the abundance of time. I stopped holding myself back waiting to have all the time in the world for things.

Scott Barlow: That is so interesting. First of all, did you play basketball?

Jenny Blake: Only in seventh grade. I moved on to softball and volleyball.

Scott Barlow: That still counts. Second I love that analogy because I believe it helps break it down. What I particularly like is that so many of us get stuck in the scanning phase and a lot of people listening are there. What I would love to do in this case is push you, Jenny, on a couple areas. For someone in that scanning phase what are two or three strategies they can use right now to be able to move into the next phase and get out of the scanning?

Jenny Blake: Again, just to be in scanning, doesn’t mean you spent enough time looking at what already is working and what success looks like a year from now. Counter-intuitively, the number one thing you can do if you are stuck in analysis paralysis is refocus on yourself and who you are. What does success look like a year from now? Really paint that picture. I have on my website an ideal day map that I think is a fun way to dig into this. Be so detailed with what time you wake up, who you are surrounded by, what type of work, how much you are earning, what impact you want to make, how are you growing?

Scanning is about people skills and projects. People – who is already doing what you want to do? Who can you connect with? Who are friends you can set up friend-tor relationships with for accountability and support. Friend-tors have been so valuable to me. It’s another place where people put pressure to find a mentor but accountability with your friends can go a long way.

Skills – where do you want to grow? If you are at a pivot point you have room to grow which is exciting. We all live for learning and growing and feeling challenged. Next is projects and making yourself discoverable. If you are scanning and super clear at least generally on where you want to end up. It may be the case that no one knows that you are looking.

I have on my website a network email mad lib where you fill in the blanks. I created it because I had so many clients that would get to a point in their search and it was time to email their network and tell their friends and family that they are at a pivot point. It says here is a little of what I’m up to, this is what I’m looking to do, these are my strengths, this is the type of organization I’m looking for. Or if you are working for yourself these are the types of clients I’m looking for, here’s what I do and here is what we can do together. That helps make you discoverable. Think about Bluetooth devices. It’s so important to be discoverable so people know you are looking and what for. Even things like blogging and public original thinking like posting content and demonstrating expertise in a public way so people come to you.

Scott Barlow: That is awesome. The perfect day exercise. What are some things on your perfect day?

Jenny Blake: I call it ideal day because I’m weird on the word perfect. In a way every day is perfect because we are breathing. I like the idea of ideal average day because my ideal day might be vacationing in Tahiti with a Pina Colada. My ideal average day for me, includes, like today, wake up, sleep in, no alarm, roll out of bed, meditate, have tea and read. I give myself permission to read as long as I want. I answer emails about an hour before my calls start. I love feeding my brain something interesting in the morning and getting inspired by ideas. This morning I was reading a book about how to look at art. It doesn’t always have to do with careers or business. Some sort of strategic work and projects building something. Connecting with friends later in the day and exercise. If I can fit all of that in and eat healthy that is a win.

Scott Barlow: I have a copy of my perfect day on a bulletin board behind the screen I’m looking at.

Jenny Blake: What’s on yours?

Scott Barlow: A couple things. One I have a fascination with getting to the point where I am working out four hours a day. I’m not there yet.

Jenny Blake: Fascinating, what would you do in that workout?

Scott Barlow: It wouldn’t be one workout. I’ve started doing parkour and strength training and paddle boarding every morning. This morning I woke up at 4:45 and at 5 a.m. went stand-up paddle boarding and watched the sun come up. We live by the lake so it’s easy to do. A few things like that are pieces of how I spend my day and interestingly enough your piece on fascination with big ideas we have in common. That is how I enjoy spending a portion of my day in one way or another.

Jenny Blake: That is so cool. I realized output is not as important to me. Part of the reason I hit my last pivot year/crisis/breakdown was I had a book, a blog, and courses but there was no big idea I believed in. I realized how important it was that big and original as possible ideas are vital and the oxygen for my career.

Scott Barlow: It’s so interesting because I swung both sides. When I was working, the equivalent of you at Google and building on the side I was doing the same type of thing. I was reading and listening to podcasts for the inputs and then I swung the opposite way when I took my business full time. I didn’t feel like I had time to read a book and I cut out podcasts because I no longer had a commute. I realized I was missing that and it was stunting a few different things, our business growth, and me in terms of what I wanted. I was missing those pieces I loved about being exposed to big ideas and acting on big ideas.

Jenny Blake: It’s interesting how just because you quit a job you think you can’t become your own worse boss. Not matter your work structure it’s easy to say I don’t have time to exercise, meditate or read books and those are the things that are so energizing and recharging and fuel everything else.

Scott Barlow: I feel like we could talk hours about this. I’m curious of a couple other things. Did you come up with friend-tor?

Jenny Blake: I did and as many things in my books I’d google concepts, because I’d be like I came up with this great idea, and then I’d see someone else had used it before. I pretty much feel that it was a simultaneous innovation situation. It’s crazy to write a book with access to so much information because every time I thought I was coming up with something unique or original from my brain I googled it and it was already out there. It was discouraging. It was different than the first time around where I didn’t feel like an article came out every day that said the same thing as my book. What am I doing here!?

Scott Barlow: I know that feeling where you think it’s great and ten minutes later you realize seven other people have used it.

Jenny Blake: There is so much information and that is why personal story is so important. Derek Sivers said “information is not the problem otherwise we’d all have six pack abs and a million dollars in the bank.” It’s not information alone and I had to remind myself that it’s sharing struggles and challenges and stories and how your brain uniquely solves problems that moves things forward.

Scott Barlow: On the friend-tor, what does someone look for in a friend-tor? How do I know they will be a good friend-tor for me? I’m going to say friend-tor as many times as I can.

Jenny Blake: Look for someone you are both genuinely excited to get together with. When you get together you can barely stop talking. You have a mutual love for resources and brainstorming. You don’t have to have the same goals but be excited about supporting each other and holding each other accountable and having weekly or biweekly calls. Someone you resonate with. Yes they are a friend but they have great ideas, give great advice, and can connect you. You can benefit each other in many ways other than just being someone to kick back and relax with.

Scott Barlow: I love this. I didn’t have a name for this until this moment but it’s been a huge benefit to me in my life and business. Thanks Jenny now I have a title for it.

Jenny Blake: I’m so glad. It’s such an untapped resource and it’s free as opposed to signing up for masterminds or coaching. We both run coaching business and I’m all for it but why not have both?

Scott Barlow: It can be such a compliment to any work you are doing with a coach or other ways.

Jenny Blake: You can share what you are learning, which is fun. My coach had the best piece of advice. In one of your mastermind groups we’d ask what did you learn in the last two weeks. It’s a great shortcut to knowledge.

Scott Barlow: Absolutely agree. This is super cool and has been a fascinating conversation. I very much appreciate you making the time and taking the time. We’ve been coordinating this for like five or six months now.

Jenny Blake: I know. I took a big post launch after the book came out. I needed a break. I thought I’d need two weeks and it turned into three or four months. But I’m back now and I’m glad we could do this.

Scott Barlow: Absolutely thanks for making the time. For people that want more Jenny Blake, where they can they go?

Jenny Blake: The best place is There are a ton of free templates and resources for what we talked about. If there are side hustlers or solopreneurs I have a private community called Momentum and I do Q&A calls twice a month. There is a great Facebook group and we do workshops every month. It’s a lot of fun and a great way to keep in touch.

Scott Barlow: Very cool. I’d head over there and check it out. I’ve had your stuff shared with me from so many HTYCers out there. It’s been shoved in my face but I started looking at it and have been really impressed. I would encourage you to go and check out anything put out by Jenny. Where can people get the book?

Jenny Blake: Anywhere books are sold and it’s on Amazon as well. There are a couple Pivot books so just search for my name.

Scott Barlow: Awesome. Thanks again. Really appreciate it.

Jenny Blake: Thank you so much Scott and everyone listening.