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From 20 Years of Misfit Jobs to Creative Entrepreneur: Amy's Career Change Story · Happen To Your Career - Meaningful Work, Career Change, Career Design, & Job Search

• 0:00
  Amy Haggerty 00:01:
• 0:01
  For quite a few years, I had this craving to get out there and do something on my own, but didn't quite have a lot of the details or thought maybe I was mistaking that for having more freedom.
• 0:02
  Scott Anthony Barlow 00:15:
• 0:03
  Something that's become a very popular is opening your own business. You see it everywhere. However, it turns out it's not actually for everyone. It's something a lot of people throw into the mix of considerations when they're unhappy with their jobs. But often, it turns out that these people are confusing things like wanting more autonomy or flexibility.
• 0:04
  And think that the only way to get to that level of autonomy and flexibility is to become their own boss. Without going into too much detail here, let me just say that it's not always the best way to gain autonomy, flexibility, or freedom for the majority of people.
• 0:05
  That said, there are certain people and certain situations where starting your own company is absolutely the right next step for your career. But how do you know? How do you know if starting your own business is right for you?
• 0:06
  Amy Haggerty 01:07:
• 0:07
  I got increasingly frustrated in each role in the bureaucracy or politics, or the things that I felt that were in my way of just being able to create what I wanted to create and make those decisions.
• 0:08
  Scott Anthony Barlow 01:31:
• 0:09
  That's Amy Haggerty. Over the past almost 20 years, Amy has had many career pivots from higher education to mental health, to child development, and many other areas and industries.
• 0:10
  And although she felt like she was being very intentional with these pivots, she continued to feel unfulfilled in every single role she had. She always felt like something was missing, and had a craving to own her own business, but could never picture what that would actually look like.
• 0:11
  This episode is pretty cool. You get to hear how Amy came to the realization that opening her own thing, as a creative entrepreneur, was exactly the right move for her career. And how she found a community of entrepreneurs to support and encourage her to go out on her own. Here's Amy discussing her indecision when it came to choosing a college major.
• 0:12
  Amy Haggerty 02:12:
• 0:13
  At the time that I went to college, I was looking at a few different majors and was really not wanting to jump into anything right away when I took my generals for a few years.
• 0:14
  And a lot of times students don't realize, as I quickly realized, that there's not a lot of majors that are built for that to leisurely take generals and then enter into a major. If I wanted to complete my major on time, I had to pick something. I decided on psychology as a lot of students in college who are interested in self exploration often gravitate towards, that was me.
• 0:15
  And I felt that it was a good fit. I was interested in people. I was interested in how people work and understanding all of that. And I also knew that it was a little open ended as well, which was comforting to me because I wasn't feeling 100% sure what I wanted to do.
• 0:16
  Scott Anthony Barlow 3:16:
• 0:17
  That's interesting. I don't think I've ever heard anybody make that comment. I've had, I would say, many thousands of conversations asking people about how they ended up where they have ended up. Because, I don't know, I love hearing about it. And I don't think I've ever heard anyone use the word choice, "it was a little bit open ended." So tell me more. Why was that important at that time?
• 0:18
  Amy Haggerty 03:41:
• 0:19
  I really didn't want to be locked into anything because I hadn't found anything that I was really excited about.
• 0:20
  And I also knew that I was going to have to go to grad school. There wasn't anything out there with a fort that I wanted to do that was in that field. So I started exploring grad school options. I had thought about becoming a mental health therapist, but I felt really young at the time, really inexperienced, and intimidated by that idea.
• 0:21
  And so I was looking, again, something more general or comfortable perhaps. And so I found a counseling related field that I felt was a good fit for me at the time, and that was an area similar to school counseling, but more so of a college counseling field, where I would help other students with their career exploration process, which is ironic.
• 0:22
  Scott Anthony Barlow 04:40:
• 0:23
  Yes, for sure. So what happened from there?
• 0:24
  Amy Haggerty 04:44:
• 0:25
  So that was the beginning of my career in higher education. I ended up in a position as an academic advisor working with students who are undecided in their majors. I really enjoyed talking with students about their potential career paths, exploring majors.
• 0:26
  The downside of that was, at the time, the rest of my team wasn't very interested as I was in trying to add more intentionality to our processes. A lot of advising and counseling was really off the cuff, I think, for a lot of the other advisors. And I really wanted to find out what works, what's the research saying, what's most helpful.
• 0:27
  And so that really meant that there wasn't much room for my ideas, it felt like. And so I started looking for another position, and my next position was the complete opposite. So it was all research-based, data-driven, and it was all creating new programs. And it was very much so creation and my ideas, and that part was exciting for me.
• 0:28
  Scott Anthony Barlow 05:59:
• 0:29
  Interesting. Okay, so help me understand then, where you started to recognize that maybe this wasn't a good long-term solution for you.
• 0:30
  Amy Haggerty 06:12:
• 0:31
  I was always looking.
• 0:32
  Scott Anthony Barlow 06:14:
• 0:33
  Really?
• 0:34
  Amy Haggerty 06:15:
• 0:35
  I was always looking for jobs. I was always looking for more education, more training, more programs. I think five days after I completed my master's degree, I was in a meeting with somebody asking about how to get my real estate license.
• 0:36
  Like, I was chronically unfulfilled from the beginning. I always felt like, I think deep down, I thought that I had settled. I think I had always felt that way.
• 0:37
  Scott Anthony Barlow 06:50:
• 0:38
  Chronically unfulfilled. Tell me a bit about what that looks like, aside from completing one set of training and then immediately going towards another. But what do you mean when you said that?
• 0:39
  Amy Haggerty 07:03:
• 0:40
  Every role was unfulfilling for almost between 15 and 20 years. I've had a lot of positions. I feel like I truly believe that I have made a lot of career pivots, and have done so in a thoughtful, intentional manner.
• 0:41
  And based on what I wanted more of and what I wanted less of, and at the same time, it just wasn't working.
• 0:42
  Scott Anthony Barlow 07:38:
• 0:43
  Okay, I'd love to talk about that then. When you say, "I thought that I had made an intentional career transition from understanding what you wanted more of and what you wanted less of."
• 0:44
  Now that you have more perspective than what you may have had at each of those times, what do you feel like was missing or not working then? Even though you were actively trying to do something more intentional?
• 0:45
  Amy Haggerty 08:06:
• 0:46
  I don't think I had the awareness. I think I was focused on the tasks and the projects and what I did in the day-to-day. And so I would reflect on the positions I was in, thinking of what gives me energy, what do I never want to do again.
• 0:47
  And I would start crafting something like I hope I can find a job posting, of course, like that. And I would find things that met the requirements of what I thought I was looking for.
• 0:48
  But beyond the tasks, I wasn't looking at some of the bigger picture items. I wasn't seeing that there were other themes, aside from the day-to-day, that were just not aligned with what I wanted my life to look like, and not having other people that I knew in roles, I think, similar to where I wanted to end up.
• 0:49
  It was hard to see that because you know what you know, and the careers that you know are what you see other people doing, and I wasn't seeing anybody doing what I eventually ended up realizing was the better fit for me.
• 0:50
  Scott Anthony Barlow 09:33:
• 0:51
  Interesting. So it sounds like then what you're saying is during many of those pivots or changes, you were very focused on the tasks or the pieces of the work itself.
• 0:52
  And I would argue, while that is important, it sounds like you came to the realization that that's not the only set of things that matter as it relates to fulfillment. And it sounds like you started focusing more broadly, at some point. What caused you to recognize that you needed to broaden your focus there?
• 0:53
  Amy Haggerty 10:07:
• 0:54
  Yes, I do think the other pieces that started to creep in were the fact that I would be in roles, and I wanted more and more power, and more and more control, and more and more autonomy.
• 0:55
  And I got increasingly frustrated in each role in the bureaucracy or politics, or the things that I felt that were in my way of just being able to create what I wanted to create and make those decisions. And I don't know if I really realized that until I started working with a coach, other than, I've read a lot of books.
• 0:56
  I've been in this field, in some ways, assisting other people looking at their careers. And it wasn't until, I think, that I started working with a coach and trying to look at a little bit more about the vision that I have for my life. I do think that the vision started becoming clearer, back to what you're saying.
• 0:57
  I think I was just looking at tasks. And then I think, as my life, my family, as I became a mother, those kinds of things happen, the life piece started to become a little more clear. But I do think I had wanted those things prior to that as well. But they were just a lot louder when I had a family and started wanting more flexibility and more freedom.
• 0:58
  Scott Anthony Barlow 11:39:
• 0:59
  So tell me then. It sounded like that you have had, I'm going to call it an inkling, or I think maybe someplace in my notes, you would call that a craving, that you were interested in your own business.
• 1:00
  Was there a particular point in time where you did finally declare, like, "Yes, this is the route that I'm going." Or did that happen so gradually that you can't pinpoint a time?
• 1:01
  Amy Haggerty 12:11:
• 1:02
  I did have a time. And I wrote it down, and I stuck it up on my board, I had this realization that I want to be a creative entrepreneur. I want to be an entrepreneur. I want to be a business owner.
• 1:03
  That was clear for a long time, but what was so unclear. But thinking of the realization when I was working with HTYC, and going back to those tasks, where the helpful part of looking at day-to-day responsibilities was, I enjoyed creating. And I enjoyed creating, whether it was writing, or something with graphics, or communication, or marketing.
• 1:04
  And I just knew those two things I wanted to create, and I wanted to do my own thing, and those two things finally came together for me.
• 1:05
  Scott Anthony Barlow 13:06:
• 1:06
  Well, I love that. And here's what I'm hearing out of that is that you were one of the things from making a variety of different changes allowed you to start to notice what are the themes between some of those changes, too, or some of the themes between the frustrations.
• 1:07
  Because it's one thing to sit down and take the, what I would say is pretty common advice these days, where it's like, make your list of all the things that you don't want, make your list of all the things that you do want.
• 1:08
  And that's become more prevalent. Also, it is maybe even more powerful, and it sounds like it certainly was for you, to where you could start to notice the trends between changes. And it sounds like one of the things that you were observing is that there's this want to be in control of what it is that you are creating.
• 1:09
  Amy Haggerty 13:56:
• 1:10
  Absolutely.
• 1:11
  Scott Anthony Barlow 13:58:
• 1:12
  Okay, so here's my question about that. I think that's super cool. I don't think, to be really clear, I don't think that having your own business is for everyone.
• 1:13
  I think that these days, especially, it's become very popular and trendy to do so. But I think that what often happens is a case of confusing the amount of autonomy that I want for what actually comes along with business ownership.
• 1:14
  That said, and I'm saying that for every everyone listening, I think that from everything I know about your situation, it lines up really, really well. And so my actual question for you is, when you think about that now, what are the pieces where you recognize do line up so well with owning your own business?
• 1:15
  Amy Haggerty 14:50:
• 1:16
  Yeah, so much of what you said was a lot of my fears. I think for quite a few years I had this craving to get out there and do something on my own, but didn't quite have a lot of the details or thought maybe I was mistaking that for having more freedom.
• 1:17
  And I got into roles too, that we had so... like, my last role had so much freedom, I only had to check in with my supervisor once a month with a little email. And I was like, "that's not..."
• 1:18
  So I don't think this is about the freedom because I have all the autonomy and freedom in the world, and it's the work itself. I think some of the ways that I felt that really lined up was, I've really always wanted a lot of variety.
• 1:19
  For one, I love researching, I love learning new things, I love problem-solving, I love streamlining, I love improving processes. I think a lot of my roles, looking back and seeing any themes in there too, or additional themes where my interest in customer service or client experience is something that really rose to the top.
• 1:20
  Everything I had done had been somewhere near there, where it was about the client having a really good experience. And I think that's something that also was something that I was interested in. And also, whether this is relevant or not, my husband and I also have talked a lot about having our own business.
• 1:21
  And so I think that we complement each other. And it's something that we've been wanting to build together as well.
• 1:22
  Scott Anthony Barlow 16:44:
• 1:23
  So here's a couple of things that I heard you say. Number one, the learning, the streamlining of the problem solving, the client experience, and I will tell everybody right now, if you don't care about clients or customers or anything like that, it is going to be really incredibly difficult to run a business.
• 1:24
  And I think we've all heard the story of somebody who's really wonderful at their craft, and then they go into business, and then they just absolutely despise it because it comes along with customers. So we've all heard that story.
• 1:25
  But it sounds like those were little pieces that you were recognizing and causing you to realize more and more that, "hey, this could actually be a thing." I mean, even beyond some of the doubts that you had. So what allowed you to move past those doubts and move into creative entrepreneurship?
• 1:26
  Amy Haggerty 17:40:
• 1:27
  I think the energy and curiosity that I really was able to access when I got excited about this was more than anything I've ever experienced up to this point. It just felt ever since I've made this decision, and had the realization, it just feels like the doors keep opening for me.
• 1:28
  I wonder about something. I wonder about a resource where I get stuck. And the next day, I stumbled across something about that very thing that I'm concerned about. I think some different mindsets too around, working on things piece by piece and taking it one step at a time, and try not to get consumed and overwhelmed because this is a huge life-career shift.
• 1:29
  And I think some days the business piece of it feels like it's a lot of research. It's a lot of learning. And so I think, just realizing that, I gotta keep going. And the alternative is to do what I was doing, and I don't want to do that anymore. I want to build something and focusing also on doing something I'm proud of.
• 1:30
  I think for the first time. Truly proud of more than I've experienced in my career. Keeps me going and knowing that I think risk and failure is inevitable, and accepting that, I think as like I know that's coming, I don't know where everything's going to take us or take me, but I know that I would rather just figure it out and take it as it comes.
• 1:31
  Scott Anthony Barlow 19:29:
• 1:32
  Let's talk about a couple of those mindsets. And how you integrate with those. I think that's almost the, maybe not the hardest thing to do, but up there for sure, is to take a mindset, and then actually apply it day to day.
• 1:33
  And I mean, they never worked perfectly. Well, I don't know, if you've figured out how to make them work perfectly, please do share, because it's usually a process from what I've found personally.
• 1:34
  That said, let's take a couple of those and break down for what you found worked for you. So you talked about taking one thing at a time or moving piece by piece, I think you had said. And so, what did that look like for you? Give me an example. Or a story of where you started to adapt that mindset and where you found that valuable?
• 1:35
  Amy Haggerty 20:21:
• 1:36
  Well, first of all, I feel like I found a community of other creative entrepreneurs. And that has been so exciting and really key to finally seeing my people and getting involved in that community, and resources as well.
• 1:37
  One of the resources I found helpful was another creative entrepreneur putting out a one thing a day tracker, Bonnie, Christine. And that was really helpful to realize, just to break things apart into– I just got to do one thing a day.
• 1:38
  And today, it might be this kind of research or this kind of training, or it might be purchasing a domain site, but I'm just going to keep moving. The risk part, what does that look like, or the failure part, I have a lot of post-its and reminders everywhere. I have them at my desk.
• 1:39
  I take time, at the beginning of the week, I keep track of some of the biggest, I think some of the mindsets I need to know be reminded of the most, I remind myself of those in reading those, I stay connected, I think, to the community. I think the community or other entrepreneurs that I want to learn from, and I think that momentum keeps me going.
• 1:40
  I think the fears kind of creep in, and then hearing other people's stories are really just like Happen to Your Career, hearing other people's stories, I think, are really motivating to me. And I think those personal stories are great reminders.
• 1:41
  Scott Anthony Barlow 22:12:
• 1:42
  How did you find that group or that community of creative entrepreneurs? You've mentioned them a couple of times. And clearly, having no access to those people, for lack of a better phrase, has been pivotal for you in a variety of different ways. How did you go about finding your people?
• 1:43
  Amy Haggerty 22:33:
• 1:44
  When it occurred to me that this is the path I wanted to follow, I had this flashback of meeting somebody within the last year, and I thought this is what she's doing. And I didn't put the two and two together.
• 1:45
  And I reached out to her right away and wanted to hear about her experience, and to connect with her, and added her to my list of outreach people for HTYC. And she was so great to talk to, so insightful, and referred me to a community that she was a part of.
• 1:46
  And so she referred me to training in a community, and just getting connected with her and someone who is already doing it. It's just so simple. But it was just really helpful in getting that much closer.
• 1:47
  Scott Anthony Barlow 23:32:
• 1:48
  When you reached out to her originally, do you remember what you did or what you said in that case?
• 1:49
  Amy Haggerty 23:40:
• 1:50
  I told her that I admired her work and what she was doing, and that I had been wanting to reach out to her, and I found this story where she was featured in a magazine, a local magazine.
• 1:51
  And so again, it was really timely because I was really nervous about reaching out at first, and when I saw that story, it really prompted me to, because I saw a lot of my experience in her story.
• 1:52
  And so I reached out to her on Instagram and asked if we could connect, and she replied when she was available and she was just really great and giving so many details of resources and encouragement, offering words of encouragement and sharing her own mindsets of how she got to where she did.
• 1:53
  Scott Anthony Barlow 24:39:
• 1:54
  That's fantastic. And it sounds like the way that you did it made it easy for her to also have a vested interest and say ‘yes’ to. So kudos to you for that. And at the same time, how do you think about reach out now?
• 1:55
  Because it sounds like when you were, let's go way back to you know, prior to doing that, it sounds like you were pretty nervous about it. Is that still a thing where you would be as nervous now, and you just would work through it? Or do you have a different view on that?
• 1:56
  Amy Haggerty 25:15:
• 1:57
  I think I'm a lot less nervous. I think, knowing how much I've learned on the reach outs, having done that on both sides, I've had so much success in being able to say that you're excited about what somebody does, and want to learn more, and realizing how many people really enjoy sharing their story as well, and helping others.
• 1:58
  And then on the flip side of that, knowing that there's some within 10 seconds of the conversation, I'm like, this isn't for me, and this is just so helpful. And so I would not hesitate as much as I had before. It was really helpful in being able to get over that. Because those kinds of connections, I think, are key.
• 1:59
  Scott Anthony Barlow 26:07:
• 2:00
  What do you feel like when... I think the thing that so many people wonder, and also simultaneously is one of the big, not the only big thing, but the big thing that holds people back from pursuing their own thing, pursuing a business venture, is finances, money.
• 2:01
  And it shows up in so many different ways, ranging from, you know, I think that I need $4.2 million in order to do this thing that may, or may not actually need $4.2 million, all the way to lack of understanding, to, you name it, like there's a million different ways this shows up.
• 2:02
  So my question here is, how have you thought about this? How have you worked through it for yourself? And then ultimately, how have you made this part work, the financial side work for you, in order to give yourself time, space to get this up and running?
• 2:03
  Amy Haggerty 27:08:
• 2:04
  Yes, I feel very fortunate in that area. I think one of the things that was key for me is I'm not working at the moment, because this is something that I want to focus on. I do have the luxury that my spouse has something that can support us for the time being, but it's just enough right now.
• 2:05
  And so we have had to make some decisions about just financially of what we're willing to sacrifice right now. We also have had to change our mindset around spending and investing in things when we don't know the outcome, which is an entirely new area for me. I've always worked with things like degrees that you do this, and then you get this job, and the salaries in this range.
• 2:06
  And this is really a lot of unknown. So I'm glad I have the support of when I'm feeling to like, why am I doing this? Or is this going to happen for us? And having that support and encouragement is important.
• 2:07
  And like I said, we've been using savings that we had put away for other things, and it's scary at the same time. For me, I think I got to a point in my career where it's more scary to just keep living how we were living. I hope that makes any sense.
• 2:08
  Scott Anthony Barlow 28:42:
• 2:09
  I definitely resonate with that. I would say that that is, at that point where I got too, as well. So yes, it certainly makes sense. What have some of those conversations looked like?
• 2:10
  And I'll just be really candid, like Alyssa and I have had many conversations, wonderful conversations, where, you know, we feel like we're in it together. And it's a shared dream and things like that.
• 2:11
  And also, when we've done it wrong, or we've done it not the best way, we'll say that's led to much more heated discussions and things over the last, I don't know, 20 years, I guess in collective, a couple of businesses.
• 2:12
  So I think that having that support, like you're talking about, falls into that category, is sort of another thing where it's easy to talk about and just say, “Yeah, having the support is good. “
• 2:13
  But getting to the point where you're mutually supportive of each other sometimes takes more day-to-day work. So what did that look like for you? What did some of the conversations look like around that?
• 2:14
  Amy Haggerty 29:38:
• 2:15
  I mean, we've been married a long time. I feel like we've supporting one another in our careers has been always a priority. We've supported each other when I think we've had a back and forth of that. And so maybe part of it is, it was my turn.
• 2:16
  Scott Anthony Barlow 29:56:
• 2:17
  It's your turn, Amy.
• 2:18
  Amy Haggerty 29:59:
• 2:19
  Yes. We talk regularly about goals and about plans and timelines. And I think a lot of those other conversations. I mean, we involve each other. I think that's the other piece. We involve each other in the details of what we're working on. And I think expose each other to our interests, and what we want to do.
• 2:20
  I just think the encouragement part, I mean, my husband will be like, "You're doing this." Like, you got this. And I think just being back and forth, when things happen, when one person's feeling, maybe discouraged, or some of those fears are coming up, the other person always comes out on the other side.
• 2:21
  And I think part of that is being married for a long time. And having experience with that kind of a dance in our relationship, I think, was important.
• 2:22
  Scott Anthony Barlow 30:56:
• 2:23
  What was the most surprising part of this type of change for you?
• 2:24
  Amy Haggerty 31:01:
• 2:25
  I think letting go of you have this identity of who you were, that's tied to your career. And I think it was really hard to walk away from, and that could have been the other piece that kept me for so long not moving in this direction.
• 2:26
  I just realized I didn't care about my past anymore, and I cared way more about my future. And so I deleted my LinkedIn account, because I was like, it doesn't matter. It doesn't matter what's out there about what I used to do.
• 2:27
  And it almost bothered me it was out there because it didn't fit who I felt like I was or where I was going. Versus other platforms that I feel like the other creative entrepreneurs were on and connecting with each other in different ways. So, just getting out of that corporate mindset that I was in and finding other ways to connect with people.
• 2:28
  Scott Anthony Barlow 31:58:
• 2:29
  I love the... What's the word I'm looking for, I was gonna say finality, but that wasn't quite right.
• 2:30
  Amy Haggerty 32:04:
• 2:31
  Very symbolic.
• 2:32
  Scott Anthony Barlow 32:05:
• 2:33
  Yes.
• 2:34
  Amy Haggerty 32:06:
• 2:35
  It felt like I think, to say there's no going back.
• 2:36
  Scott Anthony Barlow 32:10:
• 2:37
  Yeah. That's fantastic. The reason I say that is because it takes a measure of courage to do something like that. In many ways, fighting against human nature. I mean, you enjoy psychology.
• 2:38
  So, at the risk of telling you something you already know, there is so much of our behavior that goes toward avoiding loss. And whether it's, I was talking to my son, we're driving by all these storage units, because we have so many storage units in Moses Lake, and we were talking about, like, how that is an industry just founded on the human behavior of not wanting to deal with or not wanting to, basically avoiding loss, right.
• 2:39
  And people pay many dollars a month to put all their stuff in there, that sometimes they'll never see for the entire rest of their life. And they'll pay like 75 bucks a month or 150 bucks a month over and over and over and over again, in order to avoid dealing with that.
• 2:40
  So, deleting your LinkedIn account, like, there's a lot of courage that goes into that. What made you decide to do that ultimately? Like, do you remember what was the final straw?
• 2:41
  Amy Haggerty 33:19:
• 2:42
  I mean, I had thought of that a few years ago when I was contemplating a career change. It just didn't feel like it was me. I think the thing that ultimately was, like I said, realizing that I didn't, it doesn't matter what I used to do.
• 2:43
  And I know that there's so much more on that platform than that. But for me, it felt like that's what it was. And it was like, it was just out there of this career path that was never really fulfilling for me.
• 2:44
  Scott Anthony Barlow 33:54:
• 2:45
  What advice would you give to someone else who is thinking about they're in the thinking stages of wanting to do their own thing? Either from a support and relationship standpoint or from any other aspect? What advice would you give?
• 2:46
  Amy Haggerty 34:10:
• 2:47
  I think someone wanting to do their own thing from the supporting standpoint is, I want to say, giving someone else in that relationship what you want to be given and how you would want someone to be with you in that supportive role.
• 2:48
  And I feel like someone said to me, like if there's a dream in your heart, then it was meant for you. And that's really stuck with me. And that, why would I keep coming back to this if it wasn't something that I didn't want, because it kept showing up. And as much as I tried to push it down because it was new and unfamiliar, it just was something that kept coming back.
• 2:49
  Scott Anthony Barlow 34:56:
• 2:50
  Hey, if you're ready to be clear on what you want and find what fits you, I would say just email me — pause this right now — scott@happentoyourcareer.com. Put “Conversation” in the subject line. I'll connect you with somebody on my team, the right person on my team, who can help you discover your ideal career profile. Again, it's scott@happentoyourcareer.com.