190: Why You Should Trust Your Gut Intuition When It Comes to Your Career with Jason Bollman

Wherever you are in your life, do you ever find yourself asking:

Why does this not feel right?

At times we may even think:

“What am I doing?
This should be everything that I want. It should be hitting all the right things and for some reason, it just doesn’t feel right.”

Whether it is about your current financial situation, your relationship, or your job, sometimes we have these feelings that we just can’t shake.

Those feelings we don’t know how to describe exactly.

It’s that feeling at the pit of your stomach that puts a little doubt in your mind when you set out to do something you weren’t really too sure about to begin with.

And sometimes, it’s that utter and complete feeling of self-assurance that comes out of nowhere when you’re about to make one of the biggest decisions of your life — like marriage, buying a new house, or your career change.

Those feelings? That’s your gut intuition trying to tell you something. Trusting your gut intuition is important!

The definition of intuition is the ability to understand something immediately, without the need for conscious reasoning.

It’s safe to say that the decisions we make in life are usually made with our head or our heart.

But, a lot of the time with specific big life decisions, our heads will use all the logic it can to persuade us to stay in the safe zone when it comes to finalizing those big career decisions.

Many people find themselves torn when it comes to their career change.

They know and feel deep down inside that something isn’t right and they struggle with taking a chance to actually make a change in their career.

Why do we fight what we know to be true in our core?

We see how others reach their goals and we think we must follow in their footsteps to reach the same success.

But, the truth is: we don’t.

Success is defined by our own definitions and the way we reach our career milestones and life goals is up to us.


One way to breakthrough the traditional path of success that we’ve built up in our heads to be the only path of success is to listen to that little voice in the back of our head telling us where we need to be to successfully reach our own career goals (whatever they may look like).

Here’s how we can learn to listen to our gut intuition and trust ourselves enough to reach our career success.

There were other instances in my personal life where following my gut, instead of my head really paid off.

Jason Bollman

Career change requires a lot of your time, energy, and effort.

It doesn’t do you any good if you are in a constant battle between deciding to listen to your head or your heart.

Getting in the habit of creating your own space to reflect on your life and career goals and how you reach them is something you should make a top priority.

Make time to go for a run, read a book, network, or just find some time you can set aside for yourself to sit, relax, think, and reflect.

Creating a space without an agenda or to-do list to just be present to listen to your gut intuition about your career choices is the first step to find the answers you’re looking for.

I journaled — tried to figure out what is wrong.

This looks right on paper, but it just doesn’t feel right when I wake up in the morning.

Jason Bollman

What is something you can do that will move you one step closer to where you want to be?

When you find that one thing you can do to bring you closer to your career goals, you can begin to put that commitment into action.

Don’t be afraid to put yourself out there.

If you decide that you want to dip your toe into a new field by volunteering for an organization to either get a feel for their organization’s culture or if it is a position that you are thinking of switching to, make it happen.

Dedicate a set amount of time to your commitment and get a feel for what your life would look like if you made the career switch.

Trusting the work that you did by listening to your heart deserves a good try.

So, listen to your gut and take action.

Trusting your gut intuition will give you the opportunity to intentionally put yourself in a situation that you can enjoy.

By listening to your instincts, you give yourself a chance to grow your career.

If you’re not quite ready to hand over all of your logic to the decisions made by your heart, we’ve got the resources to help you keep moving forward with your career change.

Check out our career coaching.  We have world-class career coaches that will ask you challenging questions, keep you accountable, encourage you to take a step back and reevaluate, and offer you a different perspective.

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

Scott Barlow: Welcome back to Happen to Your Career. I am incredibly, ridiculously, ecstatic to be here with our guest today because he has done some amazing things with his life and journey and career very recently. What is even more fun is our team has been able to participate. He has allowed us to share in it. He has a great story. Welcome to Happen to Your Career Jason, how are you?

Jason Bollman: Doing great Scott. Glad to be here.

Scott Barlow: We are going to get to your story and changes and progression but before we do that help people understand what you get to do now.

Jason Bollman: I have just started a new role where I oversee the offerings our company puts together in how we sell our products to our clients and how the team delivers that. As part of the offerings I’m putting together there is a big focus on training. I have a couple training developers under me putting together e-learning, training guides, and training our consultants. I run that portion of the business.

Scott Barlow: That is super cool. I have had hands in all that before. It can be a lot of fun.

Jason Bollman: I’m very excited about it.

Scott Barlow: You haven’t always been doing that. This is a recent change. I’ve talked to Lisa and she’s shared some of your story. You worked with Lisa Lewis. For those of you who don’t know her you can hear her story on episode 147. Way before that you have had quite the career. Where does this start for you way back? What did the beginnings of your career look like?

Jason Bollman: I went to school for civil engineering. A little ways from working with a software company that I’m at today. During college I did a co-op program where I worked a semester then went to school for a semester. There were a lot of engineering points I liked but it didn’t get all of me. I would get involved in campus ministry and a fraternity on campus. I was being really active on campus. I realized engineering wasn’t all of me. I did volunteering after graduating and settled on a teaching program in Omaha, Nebraska. I taught for two years while working on a master’s degree. I taught middle school math. I enjoyed it but realized that teaching wasn’t for me either.

Scott Barlow: I didn’t realize you had a detour in Omaha. I’ve spent some time there. I almost moved there. There is a lot of cool things I didn’t know until I visited.

Jason Bollman: My wife and I really enjoyed our time there and considered settling in permanently but it was a little bit further from family than we’d like. We moved a little closer to home. Omaha was a great experience.

Scott Barlow: Very cool. You went there and you were teaching and determined that maybe this isn’t the right thing for me. What happened from there?

Jason Bollman: Fortunately coming from a teaching position I had a summer buffer to figure out what was next. I did some reflection to determine what would be a good fit for my engineering and teaching background and found technical consulting getting into a software space working with clients and it is technical. It had everything I wanted. Once I got into the company I started at a help desk. Not many people were willing to put me in a consulting role with my background. I started at a help desk, learned the software and showed my abilities and was able to move to consulting. Eventually I managed I team of consultants.

Scott Barlow: Back up for a second. I think you just glossed over a bunch of stuff that took place for those to happen. You didn’t walk in and start at the help desk then boom let’s get this guy to manage a team. I’m guessing that wasn’t the case. I’m curious what happened in between there that took you from one spot to another?

Jason Bollman: Absolutely. In coming into the help desk position I knew I didn’t want to be a support analyst for a career. I wanted a more client facing role. It played out, because I was eager to learn. I was on the software that focused on multi-family division and was figuring out how the reports worked and financial worked. Let me look at the development piece. It was a constant hunger going above and beyond what was expected. It helped me give a resume to the consulting team that showed I wasn’t just doing the status quo. It helped make the transition.

Scott Barlow: Interesting. I’m curious going from teaching into making that initial move, was that a difficult decision for you or was it obvious? I’m partially curious because we are in the middle of the summer and we get so many teachers that find the podcast because they are in summer and have time to reflect. We also find that a lot of teachers don’t make the move even though they feel like they should. What was that like for you and why did you decide to do it?

Jason Bollman: During the teaching program I was part of it become apparent I love kids. I think I did well as a teacher but it become apparent I didn’t have what it takes to do it full time. I struggled with the parents. I was looking to get more into the complexity of problem solving and troubleshooting. The lesson plans were consistent each year. It hit on a number of key pieces that were helpful but not the whole package. There was a lot of frustration and I was struggling to make things happen and get the analytical pieces of me that I had in engineering. I lost that in education.

Scott Barlow: That makes sense to me. Lisa has shared bits of you story. You strike me as the type of guy that can sink your teeth into difficult or complex problems.

Jason Bollman: Absolutely I love the details. Let me dive in and see things from top to bottom.

Scott Barlow: That makes sense. You aren’t getting all of that in the teaching role and you make the move to the help desk and are taking some great steps that cause you to move through the ranks pretty quickly. What happened from there?

Jason Bollman: Working as a consultant I was doing a lot of projects on my own. Running my portion of the business without a lot of checking in. I was mentoring the younger consultants and taking the portions of the software I knew so they could do the portions of the training I was doing. There was an opportunity when a manger left the company. I had expressed a desire to take on more and had proven I was doing all right in my current role. They gave me a shot managing a group of consultants.

Scott Barlow: Very cool. They brought you on board and you are managing a team of consultants which sounds awesome and from the outside looks like a great job. So what happened for you to say it isn’t right anymore?

Jason Bollman: You have it right there. It looked from the outside the ideal position. Working with clients, doing deep diving things, being a leader which has always interested me, managing a team. It seemed it would all be good. I was on the road traveling to visit a client and wondered what I was doing. It should be all that I want hitting all the right things but it doesn’t feel right. I struggled with that for a while before asking for help and pursuing a career coach. I talked to family and friends, prayed, journaled trying to figure out what was wrong. It looks right on paper but doesn’t feel right when I wake up in the morning.

Scott Barlow: What do you feel like after going through all that and you know deep down something isn’t right. What did you determine wasn’t right or was misaligned?

Jason Bollman: Great question. In part, it didn’t come out until later, but realizing there is an entrepreneurial bug in me and desire to run my own business someday. Lisa helped me uncover that. It was part of why I was struggling to pinpoint. My dad was successful working in business as an employee moving to an executive level. I thought that was the way to go. He enjoyed it. Not until after working with Lisa did I realize I have a desire to branch out and do my own thing someday. The environment, the leadership team I was part of wasn’t as fruitful as I’d hoped. I enjoyed who I managed but my upline was not one that I gelled with as much as I’d like. I didn’t feel I was on part of a team. It was a desire to branch out on my own and not being in the right environment.

Scott Barlow: Interesting. That makes a ton of sense. The bosses and leaders you are working with, whether you feel supported in whatever it looks like, if it’s not lining up, it’s one of the biggest things that have a huge impact on your level of happiness, based on research. First of all kudos for doing something about it. What was the period of time where you said I’m doing journaling and talking and I need to do something to change this? What happened?

Jason Bollman: Great question. In part it was one of my close friends. He hired a business coach. He is in the process of launching his own professional speaking, career coaching type of company and hired a coach. And talked about how beneficial it was and having an accountability partner to keep you moving in the right direction. It was partly that and my wife and closer friends getting sick of me asking the same questions. I need some professional help instead of just complaining and brainstorming with my wife.

Scott Barlow: Part of it was you seeing other people and your wife giving you the boot to stop complaining.

Jason Bollman: Absolutely, I love you but we have to stop talking about this.

Scott Barlow: Totally understand that. Been there. Alyssa will tell you.

Scott Barlow: That is interesting because I didn’t know that part of the story. It makes complete sense. As you started embarking on this journey what did you go through to get to the point. You’ve made this shift in roles. I would say it’s not the easiest thing to do. There are two things going on if I understand. You’ve made a shift to a role that is much better in alignment for now but also you still have this desire to do something on your own on the side. Am I seeing that right?

Jason Bollman: Absolutely. This is a great role currently. It is allowing me to develop skills to branch out on my own. I know this is a shorter term game knowing I’ll move on to something on my own. It’s a good gig along the way.

Scott Barlow: To be honest that is why I’m interested in talking to you. That is real world for how some of these things happen. I think many of us want to know how to get to the point where we have four million dollars and spend our days doing whatever we want. I think most people don’t realize the things that happen in between there. That is an opportunity to still enjoy yourself or intentionally put yourself in a situation where you continue to grow. I respect what you are doing and how you are thinking about it because few people do that. Help me understand what led up to this? You and Lisa had been working on this for a while. What happened? What was hard and what was easier?

Jason Bollman: It was a rollercoaster working with Lisa. It ebbed and flowed. She identified pretty early about the entrepreneurial bug. I dismissed it. It’s not for me but for others. We discussed the roles I had. We talked about moving from project management to managing product. Building the software instead of just implementing it. Went down that route, did research, applied for jobs, networked, and talked to a bunch of people. At one point my homework was to connect with a certain number of people in product management. I talked to a couple people and realized it still wasn’t right. It feels like my current job. Still not what I’m looking for. We had to back pedal and try the focusing questions again. What do you want? What do you want your life to look like in 20 - 30 years? In 30 years I’d love to have the four million dollars and work when I want and do what I want. How do I start taking steps to that? We went down the route looking for a different type of job, company, and environment. And having to backpedal when it didn’t feel right.

Scott Barlow: What was that like being in that? The steps forward, testing if it’s right, and then as you called it, backpedaling, and coming back. What was the most difficult part of that?

Jason Bollman: The hardest part for me was to sit with the topics and get deep into why I wanted to make the change. Lisa was good about asking the questions with our coaching calls. I’d have three questions I could put together easily but she’d ask for four and it was hard and five which was really hard and then six or seven. The six or seven clarifying questions really got past the surface level to decide why I wanted to pursue certain things and why I wanted my own business in the future. It’s uncomfortable to get down to those questions in your life.

Scott Barlow: It’s interesting and I love how you are putting it. It helps people understand how this really works. I think we all know logically there will be steps forward and back as you are tackling this. It’s hard while you are in it. It’s how it actually works. You go out and you have this hypothesis about yourself and you test it. You talk to people and in your case you realized it isn’t the thing at all and you come back. It feels like a step backwards but it isn’t because it allows you to move forward in a different area or get closer to the answer. So many people get derailed because it feels they are going backwards. What caused you to keep going and not being discouraged? Or did Lisa have to drag you?

Jason Bollman: There is a little kick in the butt from her. She helped me realize that following my gut or intuition has really helped me out. That intuition that brought me to coaching. There were other instances in my personal life like relationships with my wife where following my gut instead of my head paid off. Being an engineer by default I’m analytical and don’t like to follow my gut. It was a kick in the pants and also her helping me understand what my gut is saying. Put your head out of it for a minute and let’s sit with it.

Scott Barlow: Super interesting. That is actually to be honest, the reason we didn’t move to Omaha, Nebraska. We had an opportunity to move there with the company I was with. My wife and I had been talking about this and actively planning to move there because that was where they were located. We visited and loved it but then we were talking in the kitchen one day and realized we were ignoring that gut feeling. At the same time we a realized our plan was to move to Omaha to get experience so we could move back to Moses Lake, Washington. We looked at each other and said why are we doing this? We were doing the same thing you were describing. We were “logic”-ing the crap out of it with our head and ignoring our heart. It’s interesting you bring it up. For people just starting to pay attention what advice would you give them to push off some of that stuff? Our head overtakes and we ignore the gut feeling. How have you done it?

Jason Bollman: You have to create space in your life to sit with it. It started with me journaling for the first 15 minutes of my morning. No agenda, just whatever was on my mind. Getting in the habit of being reflective, sitting and asking what I’m feeling. No lists or questions. Just where am I? One thing I did while working with Lisa was using some of my paid time off. One day a week for two and a half months, 8 - 10 days where I took a day off, switched it up, and created space to go for a run, read, and do some networking, to have time to sit and think and reflect. That was most helpful. Creating a space with no agenda or to do list. Just sitting and listening to your gut.

Scott Barlow: That is invaluable advice. It is also something some people may have heard before. Creating space. What prompted you to actually do it and take action? I think so many of us think about it, planning on using the time for other things. How did you prioritize it high enough in your life? It’s clearly paid off but I don’t think when we are on the other end it’s very easy to see the pay off. If I do this it will lead to insights and millions of cash. Whatever comes with it? What did you do?

Jason Bollman: The morning journaling. I read the Miracle Morning and hearing his story, taking care of his lifesaver, visualizations, and affirmations. Hearing all those things made it seem I could get up 15 -20 minutes earlier and do those things. Why not. That was the first seed to start me. Moving to taking the time off, which is big step. I had put together a list of what I needed to make a change. Lisa is helping me see I can branch out in my own thing. Where do I want to go with this? With my analytical mind I made a list of all the things I could do. I could do a side business and jump out a plane with the parachute on the way down. I could take a part-time job to have some income. I could move to a different company with a different role. Ultimately taking some time off to have space was the best option.

Scott Barlow: Two things I take away. One it’s the smaller changes earlier on that enable you to move down the path to get to the bigger changes. Journaling allowed you to see the benefits of the time and space and reflecting. Being able to put multiple options in front of yourself to decide and what is the best fit. It allowed you to look at it holistically rather than be in perpetual what ifs. I could quit my job but then I’m scared for different reasons. Looking at it with different options allows you to evaluate differently. Ultimately get to a better position. Is that what you experienced?

Jason Bollman: Absolutely. You touched on starting small. I can get up earlier and journal. Five minutes becomes fifteen and it becomes finding a career coach which leads to writing everything down. I have a bad habit hearing people say you have to create space and take all this time off and jumping right to this. But what’s something you can start just five minutes a day and go from there. It builds on itself.

Scott Barlow: I love that. For someone on the other side of this just starting to have the same feelings you did that something is wrong, not totally sure what it is yet but they are no longer ignoring the gut feeling. What would you advise them to do having just done it in the last 6 months?

Jason Bollman: Yes I’ve been working with Lisa in January so, six months.

Scott Barlow: Super cool. What advice would you have?

Jason Bollman: Great question. If you can just take some time. Take time this weekend to sit and reflect and ask why doesn’t it feel right? What am I committed to doing about it? For me it was journaling. It helped get things moving. Maybe for someone else, it could be I don’t feel great physically and need to start exercising. It looks different for every person. I’d challenge you to find some time, whether its fifteen minutes or a half hour to sit and think about if I could just change one place where would I start.

Scott Barlow: I love that. If I could just change one place where would I start? It happens that way for every person. It happened that way for me and Alyssa. Eight to ten years ago we were in a ton of debt and it was a huge issue. We fought all the time and bad stuff happened. For us it was just the tiny start to pay it off slowly which led to all kinds of other crazy life changes. It starts with one thing. Journaling, asking a question, whatever it might be. Super sage advice. I very much appreciate you taking the time and coming on the show. Before we leave I have one or two more questions. I appreciate this it’s been awesome.

As you thought about this and making the change what parts of it were unexpected for you? Especially more recently the last three months or so. What weren’t you thinking about or what things were unexpected?

Jason Bollman: Ultimately the role I am in now is a little of my own creation. There had been someone managing the offerings. There were individuals that worked on training development but not one single team working in the same way as I’m trying to get us to work. Creating a position out of nowhere. I was surprised how easy it was after I suggested it that they said yes. I thought I’d have to do an elaborate presentation. It was as simple as saying there is synergy here and my skill set and I’d like to talk more about it and they said let’s make it happen.

Scott Barlow: Super cool. I’m curious what do you think was in place at that point already so that it was well received and allowed creating something new? A new position. Not every situation will flow like that. Seeing this multiple times behind the scenes, I suspect that you probably already created the time and place. What do you think they were?

Jason Bollman: I had started being transparent with my leadership team that I was working with a career coach realizing this wasn’t the right fit. I wasn’t sure where I wanted to go but was pursuing other opportunities. I would keep the team informed of what was going on, while I am here I am fully committed. Being open and honest and coming from a place of value that I want the team to be successful but I won’t be my best version if I stay in this role. Laying ground work, following my gut, having scary conversations. I felt it was right and it made the sell at the end much easier because I had been open and honest coming from a place of value.

Scott Barlow: I didn’t realize that was part of it. I’ve done a lot of that same thing. Probably as people hear you talk about it and how you shared it openly it probably scares the crap out of most of them. And it scared you and me but when you do things other people wouldn’t do and put yourself out there you earn the opportunity to develop trust others wouldn’t have and at the same time getting results that other people wouldn’t get which is crazy. What then took place in between there? Was it just you decided I see this opportunity I’m going to talk to them about it or was there more?

Jason Bollman: It fell into place. I had seen the opportunity and the portions I enjoyed and not having a fully formed thought. A different part of the organization was going through a re-organization, realigning to build the company for growth. We had acquisitions. I was in my manager’s office when he told me about it and a light bulb went off. Everything I’ve been thinking of this would be a perfect time to pitch it. I’ve been thinking about this and I htink it fits well with the re-organization that’s happening. He said it sounds great let’s talk to the vice president and get his insight. He was more excited than my boss. It had been marinating and I’d been thinking about it. It just came up. I’d been practicing following my gut so I put it out there.

Scott Barlow: Now I bet you are glad you did.

Jason Bollman: Absolutely.

Scott Barlow: That is amazing. Congratulations again by the way. I had only been able to tell you that over e-mail. I want to tell you face to face, or as close as we can, everyone else will hear it on audio. That is absolutely amazing. Jason thanks again for taking the time and making the time. This has been awesome.

Jason Bollman: Absolutely. This has been great Scott. I appreciate it.

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