187: How to Maximize Your Support System During Your Career Change with Rebecca Maddox


With every big life change, we encounter challenges.

Sometimes, we’re prepared for them — as High-Performers, we like to make sure we have the majority of our bases covered before we dive head-first into the deep-end of our career change. 

But, sometimes we find challenges where we least expect them.

When we look at career change, we know that taking on this big life change requires a great amount of time, energy, maybe a bit of financial planning, and a solid support system to lean on when the career change process becomes overwhelming.

One of the least-talked about topics of career change is your current and ongoing support system.

Everyone needs a support system as they approach any big life changes.

We have people that care about us and they want to be there to support us in times of need — whether it is to vent about our career change obstacles, seek advice on what to do, or to be the distraction we need from all the mental strength we’ve been exhausting to make our change happen.  

As much as our core supporters want to be there for us as we make this career change, many of them aren’t really sure how to approach the issue.

This is where the challenge comes in (where you’d least expect it!).

Unfortunately, the reason many people stay in the same place in their career is often because of the lack of support they get from their core group of friends and family.

But, knowing  to have an honest and open conversation with the people closest to you about your career change (if you want their support) is key.

Being able to navigate those relationships in order to remain authentic to yourself and your career goals is just as important as the work you put into your actual career change process.

Let’s dig deeper into your support system and learn ways to better manage those relationships as you go through your career change.


The reactions of the people closest to you as you explain your career change decision isn’t something a lot of High-Performers calculate beforehand.

The wild card is always going to be other people’s feelings when it comes to your big career change. Why?

People are risk-averse

Everyone deals with change differently.

The majority of people see career change (especially if you don’t have a job lined-up in the immediate future) as risky.

Your career change makes you vulnerable. Ultimately leaving your supporters feeling vulnerable as well, as they care what happens to you as you make this life change.

  • Nobody needs to tell you that changing careers is nerve-racking.

After the initial shock and surprise people may feel as you inform them of your career change decision, people will become nervous for you.

They may then project that nervousness onto you, which is the last thing you want them to do.

  • Some people will look through their lens of perspective and unintentionally react in a way that this career change would effect them personally.

It is almost a natural reaction to immediately think about how your decision would change their lives – oftentimes, this isn’t a positive reaction.

  • People may react with anger and frustration.

They’ll comment with:

“You’re making a mistake.”

“Is all this trouble really worth it?”

Again, this leads back to people taking your decision personally and thinking in terms of how your decision will change their lives.


Your loved ones want what’s best for you, but also may just be thrown off by this new change and can’t wrap their heads around it.

It may even be because when they think of you, they think of you in a certain way, and this change is completely out of the oridinary.

The emotional impact of others not understanding your career change can throw off your mindset and ultimately put the breaks on your career change.

Don’t let that stop you.

Knowing how your career change can effect your support system can help you be proactive in your communications with them.


If you need support to help you achieve your goals, move forward, or deal with anything challenging that comes your way, you need to:





Family and Friends

The family and friends that you keep the closest only want to see you succeed, so having the conversations about your new career intentions should be open and honest.

Be clear about what it is you need from them in support — advice, comfort during the hard times, respecting your plans to save more money, trust in your skills, etc.

If you’re struggling with some people that are having a hard time processing your career change, here is a sample script you can use to start that conversation:


Whether it is your former professor, boss, or other professional in your network, a mentor is a great form of support during your career change process.

Maybe they’ve experienced this type of change before, or maybe they know someone that can share their story.

Your mentor is there to help guide you through your career and provide suggestions on next steps as they may know your skills, experience, and where you excel.

Approach them with the same straightforward conversation on how they can best support you.


Just like your mentor, your colleagues can help you expand your network.

They also know your work ethic and can understand what it will take to break through to something new.

Career Coaches

An outside perspective might be necessary to further your progress to your career change.

You may reach a point in your career change where you begin to feel stuck.

You can lose your focus, motivation, or let your mindset get the best of you.

A career coach is a great way to incorporate someone that is impartial to your work history.

A coach is someone that doesn’t carry any predispositions of you as a family member, friend, coworker, or employee.

Having a career coach by your side as you continue down your career change path will help support you with structured guidance on that dreded question of “What next?”

High Performers know that surrounding themselves with the people that encourage and support them and their goals is necessary to make things happen according to their values.

You don’t have to stop your career change when one of your core supporters reacts to change negatively. With a career coach and a community of like-minded career-changers, you can get the support you need.

Once you are able to step away from your current situation to regain perspective on what you need to do to continue with your career transition, you will be able to find the resources you need to reach your career goals.

If you’re struggling to find the way to your new career, Career Change Bootcamp can help steer you in the right direction, too.

Check it out.


Scott Barlow: Welcome back to the Happen to Your Career podcast. I am incredibly, ridiculously excited today because we have an extra special guest. It’s not our normal guest. Its someone who has allowed us to tag along for the ride as she has made a huge career change. I’m very excited but even more so I don’t know all the details and I want to learn, so welcome Rebecca. How are you?

Rebecca Maddox: Hi. Doing well Scott. How are you?

Scott Barlow: Oh my goodness. I am so good and excited. Before we hit record and started the conversation we were chatting about what you do now and what happened for the change which is super cool. Congratulations again.

Rebecca Maddox: Thank you very much.

Scott Barlow: How do you describe what you are going to get to do. You haven’t started yet. You are in Sacramento studying for the California bar right?

Rebecca Maddox: Yes. That is right.

Scott Barlow: What do you do with that soon?

Rebecca Maddox: After I take the bar in August I’m looking forward to joining a firm in Fresno, California where I will be doing litigation and using the tools I learned in law school and putting them to good use.

Scott Barlow: Very cool. Prior to moving to Sacramento you were in the D.C. area. But not always there right? Let’s jump way back and talk about where this started. What prompted you to go to law school?

Rebecca Maddox: Diving back deep into the cobwebs. I decided to go to law school my junior year of college. No one else in my family had gone before. Before, I thought I wanted to go to med school, but then I took calculus and chemistry my freshman year and there is nothing like that to make you reconsider your life priorities. I don’t know if this is right for me.

Scott Barlow: That cracks me up. Why do you say that for people who may have not been through that?

Rebecca Maddox: I came in as a math and science person but after taking chemistry and calculus, which are pressure cooker classes, that weed out the “weaklings.” The people who are waffling. They are trying to bring out the dedicated people. I remember getting a grade on a test that was about a 50 average with no curve. This is insane. The average is failing. I don’t know what I’m doing. I reconsidered everything.

I took environmental science courses and policies, women gender classes, feminist jurisprudence. That opened my eyes - what if the law is something I want to do? I told my parents and they said “really?” I took the LSAT. I did an internship with a community group where an attorney represented the group in front of the zoning commission. I thought this was incredible. I went to law school because I found it fascinating you could use advocacy and arguments to achieve something for someone. At the end of the day I wanted to help people. That moved me to law school.

I went to law school at the University of Maryland. After I went to school I realized I had never been involved in politics. I realized I had experience with environmental organization in undergrad but I had never looked at politics but it felt like another factor. I’m in Maryland and D.C. isn’t far away. I have no kids or house what if it’s something worth trying.

Scott Barlow: I love that you asked if it was something worth trying.

Rebecca Maddox: I decided to start talking to a few people. Where do you start and go? What does this mean? I ended up connecting with an office in D.C. and worked there because it was 2013 and the recession was hard for lawyers. Because all of that people say I’m scrappy. You go see what is out there and see what you can get. That is how it lead from law to politics. Then I did that for a couple years.

Scott Barlow: Before you did that you talked to a few different people before connecting to that organization. Who did you seek out to ask about politics?

Rebecca Maddox: That is a great question. Coming from my family, extended and immediate, is filled with teachers and doctors. No one knew much about connecting with politics. I remember a friend at school was more involved in politics. There was an intern coordinator for political internships and my friend told me to talk to her. I found most of my internships and experiences through teachers saying you should be connecting. They acted as mentors. Getting into politics is a tough game. Everyone is coming in trying to prove themselves. It is a lot of networking. Meeting people for coffee and finding connections with their states and offices. It helps strip the green. It strips the greenness off.

Scott Barlow: Off of you quickly. No longer green. That is interesting. I think a lot of people don’t realize how much relationship building and networking is involved in politics. That is ultimately the way things get done or not in that world. As I know more people involved in politics I naively didn't realize that. Which is the same in every other area of life but it didn’t click for me.

Rebecca Maddox: It is an amazingly small world. There is a catch 22 if you want to work for congress. First, you need experience in politics, but then you say I need a job to get experience. That is where the politics comes in. Here is a connection and you realize the political world is relatively small. Everyone knows other people. There are even publications tracking who moves where and when. Everyone is very aware of what is happening.

Scott Barlow: I know that, because you and I had a conversation seven or eight months ago, the first time we met. You were less excited about being in D.C. and involved in the political arena. Is that fair?

Rebecca Maddox: Yes. During my time there it was exciting and interesting dealing with big issues and changes. You work with motivated and intelligent people. Some very diplomatic and great people but at the same time working at 50,000 feet hovering above ground, you start wondering about your impact and connecting with people and is it the best use of my skills. I remember people saying you have the dream. It raises a red flag when they say that and you see the truth but something feels off for what I’m looking for.

I think in that moment I started looking for a career coach because when you are in a position you have worked hard to get and put in a lot of time and you think this feels right I’m getting experience, a good reputation, it’s hard to talk to other people and know who to talk to about wondering if there is something else. Even saying to your family hey I’m not sure this is my forever fit or best fit for my goals. Everyone has their own bias. If your family supported you to get here they want to see you happy but don’t understand your thinking about leaving.

Scott Barlow: It’s the dream.

Rebecca Maddox: Granted there were great opportunities but thinking for me, my skills, and what's next, what are my options? Having an outside perspective and someone who can call you out and be accountable that is what I was looking for.

Scott Barlow: I’m curious, diving back for a half second. It sounds like you were having fun with some of it and there we are different levels of excitement at the time. What really started you down the path realizing it had changed or you wanted something different?

Rebecca Maddox: I started feeling disconnected. We would start working on an issue and something else would become more important. There were loose ends jumping around. What am I accomplishing here? I started feeling the disconnect. There is this fairness impact and the depth of the issue. When you are working on a higher level on issues you are trying to not dive too deep into the weeds but you also have to create something. I become a very versatile generalist. Looking at issues across the spectrum but diving into, running an inch deep a mile wide. Some people thrive on that and enjoy staying in the substance but more on the political forces. I found it all exciting but I’d love to dive deep and be more of an expert. Sink my teeth into it.

I started reconsidering my impact and ultimately how did I want my ideal office to look and how do I get my rewards out of work. Is it policy or one on one relationships with clients.? I think it’s the clients. I started piece by piece picking things off. When you are in the environment, when it isn’t working you know it’s something but don’t know what. It can be hard to hear your voice. On top of this my heart for my job was wandering and my heart was somewhere else. My significant other was out on the campaign trail and I thought how are we going to get in the same place. There was that coming into play. I’m trying to hold it all together but something is going to give eventually. What makes the most sense?

Scott Barlow: That is interesting on a variety of levels. You started realizing being an overall generalist and not getting to go deep was missing. You had needs and wants and life changes. How are we going to stop doing this long distance relationship? You were pulling in different areas. Its super cool you recognized the need for change. A lot of people will keep going. I see them all the time. Rather than act on the need or want the keep going. Kudos to you.

Rebecca Maddox: Thanks. When you're in the zone or doing this, especially if you have a lot of time and energy invested. It’s not all black and white, or a voice from God. The lucky people see a burning bush, but for me it’s the little itch and you say maybe, maybe, am I crazy? Everything else is going on let’s keep going. Maybe it's just me. I did that for awhile. I thought I need to make sure. I’m not handling this correctly. I need to go running and get my energy up. I need to follow up on mistakes, be accountable. You try to fix the other things.

There was a moment, for other listeners, a moment you realize something is off like you snap at someone and you didn’t realize you didn’t mean to and it goes beyond where you should it’s not where I should be something is wrong, listen to that. For me, it was a long time before I made my move out of D.C. My moment was when I went to the dentist office. They x-rayed my molars and the nerves looked like scrambled eggs. I’m not out of my 20s. I was clenching my teeth so hard at night from stress and was messing up my nerve endings. If I kept going like that I would need root canals for all four teeth by the time I was 30. It made me sit down and say something is wrong. Something is really wrong. I tried to keep swimming and going, keep focus, everyone has issues. But eventually something starts to give and something is off. I think the hard part for me was negotiating with my family and friends. Not just in the workplace because I’m trying to be a professional. Tyring to dedicate myself. But with family and friends telling them your idea and appreciating their support, that I think it’s worth a shot.

Scott Barlow: How did you handle those conversations? That is a real thing for nearly everyone even if you have a really supportive family. That is still a big gap. They want to know why. How did you approach those conversations?

Rebecca Maddox: The hard part when thinking of making a change is either - I’ve had several reactions, people are usually nervous and want to be helpful, loved ones in particular, but they don't know how to approach the issue. I’ve had ranges. Some people say go do what you love. That is broad.

Scott Barlow: Just do it.

Rebecca Maddox: Or I once had someone ask me what is the one thing you need in life. I had to look back and say I don ‘t know food clothing shelter. Where are we going with this?

Scott Barlow: Water obviously.

Rebecca Maddox: Yeah. In approaching that I had to realize that while I was feeling vulnerable in my search and thinking broadly others were also feeling off kilter because they want good things for you but think of you in a certain way. Having honest and open conversation is important. Some people truly didn't understand and were angry; which I’ve run into a few.

Scott Barlow: Really. We’ve seen a lot of that happen. It seems like there are a variety of reasons. It is something that most people don’t expect when going through this. It’s good you bring it up.

Rebecca Maddox: it's something that came up for me because it threw me off kilter in my job search. The emotional impact of others not understanding or being frustrated. There is validity there. I think my moment of wisdom was when someone very close to me said I think you are making a mistake why are you moving cross country. They may be mad at certain things if you are making yourself or others vulnerable financially. That’s something to put on the backburner. But I had enough in savings. I had saved up for this. The other thing is the logical support wanting support where I was. I had to say you are my friend or loved one, I love you dearly and your support means so much to me. I need to give this a try. If it doesn't work out I will be okay. I just need you to trust in me in my skills that it will be okay. If something else comes up we will troubleshoot from there. Here is my plan and where I’m going. I’d appreciate your support. That is how I went about it. Whether it is the best move or not it worked for me.

Scott Barlow: What you verbalized is a great script that we’ve found has generally worked. When you explain why you need to make the change and ask for support and even explaining that it will be okay for these reasons it helps people move from point A to Z. Many times it seems like that when you are making a big life change the people are looking at it through their lens of understanding and whether it would be good for them. Not intentionally. They have your best interests in mind but they are looking at it through what would be good for them accidently. That’s how our minds work. Of course those big changes wouldn’t be good for you Rebecca because it’s not good for me. Have you found that?

Rebecca Maddox: Yes and I’ve found it's not as much as I want it to be a clear cut straightforward moment. You imagine me in this way because of this one thing for you. There is never just one thing it’s an emotional process they have to go through. It’s difficult to explain to a bunch of people and exhausting talking about it with each person. At a certain point you have to know who your main support is. Talk to those people first and know to a certain degree it will percolate through. Over time it gets better. People ease off. Especially if it works out.

For me after I left, people have noticed little things. I’m laughing more. My hair is blonder because I’m outside more. Little things. People say maybe it’s not so bad. The idea of dropping things and moving to a different opportunity is risky and many people are risk averse and nervous. They wouldn’t do it. There are many hurdles of how people make their own decisions. Maybe they just wanted you there, they bragged about your career, they thought it was what you wanted, they don’t know you anymore. That is the untold story with the career change. How your support system works.

I would recommend, a piece of advice given to me, know who is supporting you. Surround yourself with them and check in. You need their support to accomplish your dream or move forward or do challenging things like losing five pounds or moving cross country. Check in with those people to know you are supported.

Scott Barlow: That is amazing advice and it's hot of the press because you have just been through all of this. Even I forget, I’m surrounded by it all the time, and have found these same things myself. Making multiple career changes myself I didn’t anticipate the emotional toll with the conversations and taking and explaining the actions and trying to get support. You never imagined it goes along with it. So many people stay in the same place because of this.

Rebecca Maddox: It is hard and risky. What is on the other end of the yellow brick road?

Scott Barlow: What if the wizard is mean?

Rebecca Maddox: You never know and take the leap of faith. Will the road lead to the canyon will the bridge fall beneath you? Will people be there to support you? You don’t know but hope so. For me I made the decision for where I was, when my job ended I didn’t have anything else lined up and that made other people nervous too. I was making this cross country move which is hard enough, but getting the time and space too is a luxury, not everyone gets that.

Scott Barlow: In order to be able to do it in a healthy way there are prerequisites. I’ve done the same thing with the same reactions. Really, you just aren’t working?

Rebecca Maddox: At that point of time having that cushion, financially, was my first line of defense to say we are fine. We will work it out. I’m working diligently on it. Everything is paid and good. During that time, because people are nervous and project it on you, in addition to your own insecurities about whether you can do it or not. The negative voices come. What was helpful for me during the coaching experience and along the way is learning it is important to give yourself some grace. I would recommend Elizabeth Gilbert’s Big Magic. Listening to her was helpful. This idea that you have a creative muscle and you need room to breath. During the process I felt pressure to find the job. I found pressure to find something justified as the bigger better thing. There is the idea of where is the job, the one. Are you moving up in the world?

Scott Barlow: Well you just told all these people you are making a big change. Own up.

Rebecca Maddox: Now you have to. People are depending on you. How is the job search going? O my gosh, stop!

I believe in cross pollinating ideas. When Elizabeth Gilbert was talking about artists who put so much pressure on themselves to create their whole career off their art that it kills their creative muscle. I felt the same way about finding a job. This is about finding what is my best fit for my skills, the next best step in my career to be successful. The average person might put in 100% and get 100% back, I might put in 100% and get 150% - 200% back because I’m doing what I’m supposed to. That is what I’m looking for. The advice to ease off, thinking if I have to have a bridge job for a moment, I can do that. It’s most important I find the next best step for me. Coming into a new place, there is a lot of networking, meeting with people understanding how they look at your resume and how to break through. That takes time. I’d recommend Elizabeth Gilbert.

Scott Barlow: I’ve had several people recommend that book. I’m curious as you went through this process and as you called it finding the next best step for you, how did you end up working with Lisa and what are the one or two biggest things you took away from those interactions?

About your next best thing.

Rebecca Maddox: Working with Lisa, she’s great and I loved working with her.

Scott Barlow: We are talking about Lisa Lewis and you can hear her story on episode 147.

Rebecca Maddox: She was great. I decided to start working with her because as I was diving into the bootcamp on Happen To Your Career I was trying to think broadly. Should I be a lawyer? I took the What Color is Your Parachute approach. I started to dig deep and laying a foundation. I started working with Lisa when I saw I was pulling some things out, strengths and interests, but it was murky and I didn’t know how to move forward. Not knowing where you want to go, some people see the burning bush and others don’t. I did not. How do I move forward and develop? I was hoping to get that burning bush moment but didn’t. That was when I felt stuck.

I called Happen to Your Career and decided to reach out to a coach that is impartial with no vested interested like my family. Not like people in my network that may see me in a particular way. Some people are so outside of the job search game that they have general advice but not what you need. It was helpful working with her because she helped me think about structuring how to talk to people about what I’m looking for and moving forward. There were moments when I would avoid an issue in my search and she would call me out and ask what I thought I was protecting by avoiding it. You aren’t avoiding it because you are lazy, my phrasing. What are you trying to protect yourself from that you feel vulnerable about? It was a great point and I had a breakthrough journaling about it.

She helped through the interview process, not just pragmatically like the baseline things, but the question of my inherent bias trying to find a job in D.C. As a lawyer in 2013 when there were tons of lawyers. You felt disposable. At that point having to scrape by for a job, I had an inherent tendency to try to form myself into the person I thought they were looking for in the interviews rather than presenting here is where I am and what I’m looking for. I’d love to work with you in the future if this works. I had a bias to get the job and do whatever it takes. In reality just getting the job can lead to a mismatch and miscommunication and assumptions. The employer doesn’t do what you want. There is desperation. It came through even though I had money to cover my bills. That was my inclination. Working with Lisa was helpful to strip down the extraneous and being more authentic. Without precluding the opportunity but being honest about where I’m coming from. It changed the interview process for me.

Scott Barlow: That is a massive mindset switch.

Rebecca Maddox: Huge. It felt bizarre at first. I felt naked in the room. I think Lisa called it radical authenticity and it feels really bizarre. There was one interview that I thought once I say this stuff this thing is done. I’m interested in the job but I don’t know how long given what the position is because I would outgrow it quickly. They had the same concern. But this would be my foot in the door because there are few opportunities. Talking to Lisa about it, I practiced, then went into the interview. I had practiced a line. And once I gave it, I would be interested in growing from this to other opportunities in the office, can you tell me what you are looking for. It centers your position of power. When I walked out of the office I knew I wouldn’t get a call back but I felt okay with it, which I wouldn’t have before. Before if I hadn’t tried to meet what they were looking for to get the job I would have let myself down for not keeping my options open. But I was being honest. They deserve to find someone who is the best fit and I deserve a job that works for me. I felt more comfortable. I was a shift in narrative that paid off.

Scott Barlow: It is so interesting but sadly not intuitive for people. You said it felt awkward to be radically authentic and vulnerable. It’s not the norm and scary. I’d say 100% of the time it creates a better result. It is super scary in some cases. I don’t think I believed that until one interview that I went into. I thought I was interviewing for one position and they started talking to me about another. I said I’m sorry but I’m here because I’m interested in this. He said we don’t hire people for HR manager unless they have experience or been in a role for many years. I said I’m sorry but that is what I’m interested in. He said why are you here then. We had a conversation from that.

It was scary and I remember thinking should I just get my foot in the door. They ended up offering me the position I wanted at a $20,000 increase more than I would have gotten. I’ve seen that hundreds of times. That same thing you are describing. It’s hard. Here is my question. Looking back at all of this at this point, you got the opportunity to work with Lisa, not everyone gets to. What advice would you give people as they are thinking about making a change? Maybe they are back in a place feeling that itch. They snap at somebody and realize that work is impacting their life in ways they didn’t anticipate. What advice for those at the beginning?

Rebecca Maddox: If you are at the beginning you owe it to yourself to give it some time. Try something. Look at your options. Go talk to somebody, talk to friends. Do you know someone who does this, I think it's interesting. Meet for a coffee, a five or fifteen minute conversation, saying hi I think what you do is amazing I’m trying to figure out what it means to do your job. It's worth it. It is no pressure. That is how most people find jobs.

If you are in that moment thinking you are so entrenched where you are and moving to a different opportunity is a joke, maybe you are right. There is a good chance you are wrong unless you are in an extremely niche field because skills are transferable. If it’s something hitting you hard and impacting those around you. When it goes beyond just you, it is worth trying the boot camp. Do a strengths finder analysis. Get a different perspective. Take a breather. If there are people in your life that say you get your job and stick to it. That is what you do. That is not the world we live in. It's a game of chutes and ladders rather than plant your roots and see how far they go. If people are telling you you have the dream but something doesn’t feel right, that is fine. Trust that. If people are angry they will come around. Especially if you know it’s going to make you and everyone happy, do the right thing.

Scott Barlow: That is amazing advice hot off the press. I have found zero things worth doing in life, that are big changes, are going to be incredibly easy. Very few are going to fit that. Very close to zero. Anytime you make big changes someone will disagree.

Rebecca Maddox: Definitely.

Scott Barlow: Thank you so very much for making the time and taking the time. This has been super fun for me because we got to talk way back when you were thinking of making the change and now getting to talk. Lisa has kept me up-to-date in the middle but I didn’t get the juicy details. This is super fun to find out this after the fact. Congratulations again.

Rebecca Maddox: Thank you very much.

Ready for Career Happiness?

What Career Fits You?

Finally figure out what you should be doing for work

Join our 8-day “Mini-Course” to figure it out. It’s free!