Escaping the 9 to 5 with Jenifer Hill
Jenifer is a trained mental health therapist with extensive knowledge of human behavior. She is a I.C.F. Professional Certified Coach (P.C.C.), Board Certified Executive Career & Leadership Coach (B.C.C.), Certified Healthcare Coach, Professional Clinical Counselor (PCC-S), Meditation and Mindfulness Teacher, Leadership Development Consultant and Facilitator. Jenifer yields a global perspective, up to date knowledge, fact-based resources, candid feedback, and a deep understanding of her clients. She is dedicated to empowering leaders and individuals with self-awareness, emotional intelligence, mindfulness, well-being, and innovative thinking so they can accurately identify their purpose and execute a clear personal and professional vision.
*Resources mentioned during the episode*
The Outsiders Business Incubator: A year-long business incubator for experienced corporate professionals who want to translate their skills and passions into a profitable and enjoyable business.
Okay. Hello everybody. Welcome back to this month’s Escaping the 9 to 5 interview. I’m here with Jennifer Hill. Jen and I came across each other, I want to say on Clubhouse-
Anna: … which is funny because I have to admit, I haven’t really been active on Clubhouse recently, I don’t know about you. But nonetheless, I love these random connections we make and I’m really happy that we had that wonderful conversation at the time and that we’re now staying connected. And now that I can bring your story of transitioning out of your career and into something new and impactful. So Jen, why don’t you tell us, what were you doing before and what are you doing today?
Jen: Well, thanks so much first for inviting me. I appreciate it. Happy to connect with you as well. I was looking forward to it. So what I was doing before, I’m a mental health clinician by training. So I worked in everything from a psychiatric floor with inpatient clients, to private practise, working in the community. Really any and everything that you could think of when it comes to being a therapist and working with clinicians and supporting patients, one-on-one or in group settings. And I got burnt out very quickly. The average burnout rate for a therapist is six years. And I was around that. A little bit longer. Whenever I actually got recruited to leadership development, working for a large talent management consulting firm. And I ran hard and ran fast from the one area of mental health as being an active therapist and having a full caseload and jumped right into this aspect of management consulting and was travelling about 97% of the time.
So I got my six weeks of allotted. Thank you, European vacation time versus the U.S vacation time, which is usually one or two weeks. And I worked there for about four and a half years and was working all of the time until I made the big transition away from the, I call it, the nine to nine because it was definitely not nine to five. The nine to nine. To working for myself and really living my ideals in being able to do the work that I want to do, while also getting to put in the personal work and the personal fun that we’re all meant to have. So, I know it seems to be maybe idealist for some, but for those of us who are on this conversation and listening to this obviously there’s opportunity to escape that nine to five.
Anna: Absolutely. I was going to say, a management consultancy, not exactly an easy thing to move into. Not exactly the best choice if you’re already burnt out, I feel. But that’s really interesting that you said the six year average burnout. So just out of curiosity, what is happening there? Is that something that’s just accepted and people do leave and move on to something else? Do they suffer and come back? Is there something being put in place to manage that?
Jen: Great question. So, all of the above. When I was active with a caseload, as a clinician, people just talked about burnout like it was “I’m tired”. It was very common that we would have that conversation. It was almost the expectation. Like “When I was burned out, I need a break and I need a rest.” But you just kept on going and in that field of medicine, and I see this even now with the support that I give to physicians, it was as if I just didn’t really know anything else, right? That’s all that I knew. It was just normal to feel burned out. And so you say this aspect of management consulting and like, “Oh, that’s an interesting approach to take.” But for me, it was an escape. It was such a whole different world, right?
It was a different idea, a different way of living and it was a different way of doing things. Of course, I was ready and willing to jump because when you’re in that field of medicine, it’s so hard to transition out because you don’t know anything else. So, in retrospect, it’s like, “Wow, that was a really interesting jump to make.” But it actually catapulted me into recognising that there’s so much more out there and there are so many different ways to do things. And it really catapulted me to my ideal state in terms of being able to be independent, to be free, to have choice and agency over my life. And so it was an interesting transition time. [inaudible 00:04:27] a lot more work that came with it, but it really expanded who I was as an individual and really forced me to focus on those almost foundational things, right?
What are my values? And what do I want out of life? What are my non-negotiables? I just never considered that. I was all consumed with what I thought was supposed to be an adult career or lifestyle. And I see many people are still like that and I get it, right? It’s hard to consider something else when that’s all that you know because you live it day in and day out. So to consider what is next or what is bigger, it’s exhausting.
Anna: I don’t think we do, as you say, consider our values. What are the non-negotiables, it’s just not something we… As you say, we just follow the adult path of what we’re supposed to do. And it’s almost the emperor’s new clothes. If you don’t look and think, “Hang on a second, why does nobody realise this is a bit odd?”
Anna: But management consulting, of course, an amazing set of skills for you to have. And I imagine, as you said, really set you up for then running your own business. And I imagine less emotional engagement versus therapy. You give so much of yourself and obviously very difficult things you’re dealing with. So I guess I can see in that respect, that it’s almost relaxing for you after those years.
Anna: But I guess moving into the more recent change then, to actually going out independently and answering all those questions about your values, what was it that led to that trigger to move away from the complete corporate career and actually go out on your own?
Jen: Yeah. So it really came to a head when I considered thinking about the ultimate future, right? What was going to be next for my life outside of work? I was really working at the top of my licence, if you will. People often say that as well as, it was really successful. In my role, I was running executive coaching for the Americas at a very young age and I enjoyed my work. But I was getting to the point where it was just becoming the same thing over and over and over again. And for some people that’s fine, right? They are absolutely fine with that. But for me, I feel like my personality as well as just the spirit inside of me, the longing inside of me was unsettled. And I often liken it to the way that elephants are trained. So bear with me for a moment. Have you ever seen an elephant trained before?
Anna: Not in detail, I must admit. You’ll have to enlighten me.
Jen: Most people haven’t. So actually I taught in Uganda and I was teaching motivational interviewing and I watched them. They were working with this new elephant. And so I talked to the man afterwards and he had said, “Jen, we tried to train the elephant by just yelling at him, telling him this is what you need to do and whipping that elephant into submission.” And some elephants, completely submissive. They will do it and they follow. No problem, right? And some of them don’t even require much yelling or much forms of submission. But others, they have an active spirit, is the way he said it. And so that what they’ll do is they’ll put two other elephants that are trained beside them and that elephant in the middle follows and starts to adjust. And it starts to conform. And when I was working for that firm, I started to feel as if I was conforming.
And the kicker was though, I was still that active spirit, right? There was still that unsettled aspect inside of me that I could look to my left and look to my right and say, “I understand why we’re doing this. It makes sense. But it doesn’t make sense for me.” And so that disconnect started to happen. And I realised that I wasn’t even really tied onto those other two elephants, right? The elephant that says you must work nine to five, the elephant of society that says this is what’s normal, right? You go to work every day and you drop your kids off and you come back and pick them up. And it just didn’t settle with me. I never really allowed those ropes to be tied to me. And so what happened is I realised, it’s no judgement those two elephants.
It’s not that they’re doing anything wrong. But that wasn’t for me, right? I knew that I needed something different. And so for me, that looked like really starting to create my reality and focusing on the things that I’m passionate about, the things that matter to me, the things that I’m good at and really starting to dive in and say, “No, this is a non-negotiable for me. I want to be, at that time, I want to be with my now five-year-old. I want to be with him more than I’m not with him. I don’t want to drop him off somewhere.” Not because that’s a bad decision, but because it didn’t settle right with me. I don’t want to be travelling all the time, again, no judgement . But for me, that didn’t fit right at that time, that season in my life, that spirit inside of me, it just wouldn’t shut up.
It just kept on roaring and trumpeting to continue with the elephant example. And so for me, that took a lot of introspection, looking at my personality type, looking at my fear and any grown person, looking at my ego structure to say, “What is needed for me to feel secure and for me to have the things that I know are never going to go away?” Unless I actually just take them head on and say, “This is what it is.” And so for me, that looked like working independently. It looked like being an entrepreneur. It looked like creating my own schedule. It looked like really hustling at the very beginning and trying to figure out what the heck I’m supposed to be doing and what I actually want to be doing.
And slowly but surely the things come together. I’ve learned that if I’m true to myself, if I’m true to what is actually inside of me, instead of always looking at the elephants and the left and my right, that it tends to work out.
Anna: Gosh, that metaphor is so interesting because, as you said, we’re not tied to them. But at the same time, if we’re looking left, “Oh, they’re doing the same as me. Okay. Well that must be what we’re supposed to do.” And you don’t really think anything of it. Do you? And then you’re just trundling along, marching along, whatever the Disney song is for the elephants marching. But I think that’s an interesting one, isn’t it? That we’re not in any way forced. We have the option. But we can’t see anything else. We are not aware that there is an alternative, I suppose.
So what were some of the fears that held you back? Or were there any doubts? What were the challenges as you navigated that transition into following something that felt right but of course, there’s always things that hold us back, right?
Jen: Of course, so many things, right? I mean, imposter syndrome, of course, right? Like who am I to come into this field? I mean, I worked specifically with healthcare leaders and physicians, and even at a broader sense in leadership. It was like, “Who am I to come in and tell individuals who have been leading teams for, in some cases, longer than I had been alive at that point.” Right? I’m like “What to do as a leader?” So, of course those thoughts sneak in. And then just overall judgement , first off, of other people, right? And I really don’t think that they had that negative intention, but it’s very easy to judge other people that aren’t following the elephant. So it was like, “What do you mean you’re not going to show up and be in that office and just… You take your kids to daycare. What are you talking about?”. Right?
“You have the nanny come, what do you mean?”. Just that constant questioning was really hard to sit with, right? And being confident because if we’re all honest, nobody knows really what the heck we’re doing. Nobody knows. Even if you’re employed by someone or you’re self-employed or somewhere in between, nobody knows. Every day we’re trying to just figure out this life. But when you realise that, that is the truth. It’s freeing and really overwhelming at the same time. And it’s for people who need that stability like myself, my ego structure, my Enneagram is an eight. And so wanting to have that stability and that security was probably one of the largest challenges that I faced at the very beginning and continue to face that because I like to figure out what is next and I like to strategize.
But when you’re on your own, it’s like you’re strategizing with yourself. You’re figuring it all out. You are the security for yourself. And that can be very overwhelming and quite frankly, scary. And at times, you just want to say, “Oh, that’d be so much easier if I just called so-and-so and I could just show up and get the paycheck.” But that wouldn’t be true to who I was. And so it takes a lot of courage and it takes a lot of authenticity and honesty to be self-employed and to do it right. Not just to go for the money aspect. I mean, that’s fine for those who are seeking that piece. But for me, it’s finding that freedom. But it’s a constant challenge of the freedom from my mind, one elephant and the freedom from society and cultural expectations.
So that was a lot there, Anna, sorry. [crosstalk 00:13:45].
Anna: Yeah, there’s certainly things I want to pick up on. But I mean, I’m sure people can go back and listen again. But yeah, the freedom of course is such a key message that people come with again and again. Other people’s fears, they’re projecting, of course, their own insecurities. I always say that scary and exciting do come together. It is such an empowering, but also frightening thing to know, “Hang on, there’s no one I can just copy now.” I mean, the same is true really in a corporate career, but it’s just that we have that ladder and it’s like, “After this, I should hopefully get that promotion or I do this”. And you have mentors. So both positive and negative, you’ve got the security and the guidance and in a way we were rebelling against that. But at the same time suddenly, if no one’s telling you what to do, it’s just you, as you say. You’re strategizing with yourself, there’s no one to tell you what to do, what not to do.
So it’s incredibly freeing. But the other side of that is that you’re completely overwhelmed because there’s so many options. So I think structure, you mentioned is such a key thing. And of course, having the right mentors and coaches around you, having the community, having a supportive family, whatever that looks like. So definitely in the imposter syndrome, of course, “Who am I to believe that I can do all these things” and so on. So, where did you find the support, personally, to be able to overcome so many of these difficulties to get to where you are today?
Jen: I started looking at the coaches and the consultants that were doing similar work, right? So in the same idea of they were independent, right? They might’ve been working for some firms and gigs here or there. But really they were running their own ship and just asked for their wisdom. I didn’t ask for anything outside of just “Share your story with me.” And I found very quickly that there are so many people who are willing to impart their wisdom, right? They’re willing to share. I mean, I’ll never forget I met with a female business owner that… She was highly successful in this field and she gave me very practical advice about how to create a coaching network and how to have clients. And she said, “You need to identify your revenue stream” and specifically she gave me, she said for her, it was, she was connected to five consulting firms.
And that gave her about 70% of her income because looking at five firms, at least one is likely to have work out of the five. And so it’s something so simple, right? And so it’s like, “Okay, I can strategize for that. I can build relationships with five firms that I believe in their values and I appreciate their work. I can do that. Okay.” And so it was a very clear piece of advice. But it was just from her experience, right? It didn’t require anything of her time really. But just sharing and so looking at individuals that I saw that it was evident that they are living our values. It was evident that they were striving for who they are and not just for the next thing. And so that was really helpful for me.
Just connecting with people. A lot of people through LinkedIn are just willing to share. They’re willing to connect, they’re willing to have 20 minutes, 15 minutes, 30 minutes, whatever, to just share their story.
And so for me, it was that awareness piece of, with my personality, my ego structure, I still need some form of connection. I still need some form of stability as evident by concrete example of, I need five firms connecting with people. Even if it was virtually pre COVID, that still is a lot of the way that I connect with people and really starting to identify what is my current need and my current needs. And really strategizing around those things. And for everyone, it’s going to be different, right? For some people, they want to have a clear flow to their business. If that’s the case, create the flow.
I learned very early on, just listen to what is inside of you, what you need. And again, don’t look to the other two elephants because some people will say, “Oh, you need to have three business coaches.”
Yeah. Coaching is great. Obviously I’m a coach.
Jen: But I might not need coaches, three coaches, right? I might just need one. Or I might only need one for six months. So being very keen into continuing to listen what you need. But also having those people around you is really important. So whether it’s a coach or just somebody who is willing to share 15, 30 minutes, to impart their wisdom or somebody who is willing to go along the ride with you, right? Collaborating with other people who do similar things just to commiserate and support and celebrate, right? Those are the three words that I’ll often use, let’s commiserate, let’s support and let’s celebrate because those are the things that often we miss, I feel like, as entrepreneurs. We don’t get that opportunity to do those three things that we would get in a traditional setting.
Anna: That’s true. Yeah. I always think of cheerleaders and accountability partners and mentors and coaches. And as you said, it’s the different types of support that you need. It’s a good point that the elephants still exist when we’re working for ourselves. Because again, especially with social media you’re seeing “Oh, but that coach is suddenly talking about doing it this way. And this other person has that many followers.” It’s that comparison syndrome, comparanoia, whatever. And suddenly, once again, you’re looking for that stability, I guess, and security.
I think, as you said, and that’s what I’m all about, is you need to design and build your business around your style, your preferences, your definition of success. And unfortunately that means they won’t be a carbon copy anywhere. But that’s also what’s unique and exciting and creative and so on.
So yeah, I mean so many interesting pieces of that. And I love what you said as well. I mean, a lot of us are very hesitant to network and it feels a bit uncomfortable to reach out to people on LinkedIn. And we’re not very public [inaudible 00:19:16]. But asking people to share their story over a coffee, albeit virtual, perhaps. Everyone, almost everybody, is willing to share, very much willing to impart their wisdom and so on. So it’s not even… It’s not actually that difficult, I think people will find that if they start having conversations, I hear that again and again.
Jen: Yeah. One concrete example to tie all this in, that I use for myself and I use with clients is called a personal board of directors. So everybody knows about what a board is, right? But a personal board, even as an entrepreneur, they don’t have to be formal in that way. But thinking about what are your current, not just goals, but what are your current ideas? Right? What’s ruminating in your mind? What’s setting in your heart? And who around you could potentially support, challenge, advocate for that idea?
And so for me, I often will say this to clients, and this is again, true to my own life, is that my personal board is seasonal, right? And it might be literal or figuratively. But it’s seasonal in the way that I have a rotational board, right? So it’s not all the same people. There might be some people that hang on for a little bit longer. But I remember when I first started targeting this idea, once I realised I’ve coached a lot of physicians and that I should really get some specific training on that.
And so I started to look at physician coaches and really just networking with them and connecting. And so one of those physician coaches, she was willing to meet with me three times in one year. And the three times it was one hour each time. And I have very specific questions that I wanted to ask her. And she was willing to share her responses and ideas. And she was a part of my personal board for that year.
And then I have some people that I was working on some personal goals. I often laugh, I’ll say, for the longest time I was married to my work and my husband just happened to be there. And I can laugh about it now but I remember really being intentional with putting someone on my personal board who… It’s not that I want it to be this woman because she was a stay-at-home mom of four. Never could I do that. That’s way more of a strength and a grace than what I have. But she was very intentional with her relationship with her husband. And so I met with her and I just wanted to hear her story and any ideas that she had to start to transition so that my values were matching, my actions were matching what I wanted my values to be.
And so that personal board can be somebody that does the same thing as you. It can be something that is completely different. But connecting those people back to what it is that you’re trying to accomplish, what it is that you’re trying to learn or experience. Whatever that looks like for you. I found it extremely helpful to have that personal board and to stick with it, right? Just be so dedicated to a personal board. Otherwise it’s easy to just get into that hustle mindset. Like “I need to do, do do.” Without really experiencing and connecting to other people.
Anna: Got it. I’m so glad you raised that again because I remember how powerful it was, you said last time and shame on me. I’ve done nothing about it. But I just loved it when you said it last time. I’m going to make a note now to think about it. I think it’s such a unique idea and yet so powerful and so obvious in a way because the company has a board and having that, it’s obviously not formal. It can look in different ways and so on. And as you said, it’s seasonal, it can change and so on. But I mean, even just thinking of the types of coaches you work with, let’s say, if you’re just looking at coaches. But I go through phases, I’ve had a few now, they’re very business focused, which is great. And that’s what you need. If you’re focusing on income, you want to grow and so on.
But then I feel like I’m missing the broader life side of things. And then other times you might be working through more personal things. I have a fitness coach now. It’s even those areas. It’s quite interesting to look at. And I love that example you’ve given, not so much a role model, I guess, but someone you can look to, to bring wholeness and other sides to your personality and your life that maybe doesn’t come so naturally to you. So that’s such a unique and such a powerful idea. Thank you so much for reminding me.
Anna: And I hope that’s a new idea that the audience can take on board as well. And what’s the best part then? I know you’ve already shared a little glimpse of the positive experience you’re having now. But what do you love about your work and lifestyle these days?
Jen: You know, so many things that I am just so grateful for. I’m so grateful that even just this morning, before we were on this call, that I got to play with my boys outside and run around and catch butterflies. And I wasn’t worried about anybody waiting or anything sitting there because I’ve been very intentional to be with them and then to be with my business and being able to have that adjustment. And I don’t call it balanced. I call it fluidity, right? Work-life fluidity. So having that fluid lifestyle with structure, because my personality needs that but having that fluidity to be able to say, “I’m really going to lean into this right now.”
And I guess I would just call it being present. Now that I’m saying it. Being able to have that freedom to be present and to recognise this is what I want to do right now. This is what I need to do right now. Instead of the elephants saying, “This is what’s next.” Right? So I really have recognised the elephants and being independent and having been self-employed I know the elephants are there. And so for that, I’m so grateful. That level of self-awareness to understand the things that are pushing me, the things that are pulling me. But really being able to have that intentional decision about what I’m going to choose to be present with and the power associated with the choice that we all have, every single day.
Anna: And if someone really resonates with this message, “Oh my goodness, yes, I’m surrounded by those elephants. I feel like I’ve fallen into step with these.” What advice would you give them to free themselves or begin to raise their awareness and take this new awareness to actually make a change and maybe bring out that more active spirit in them?
Jen: So first recognise that, more than likely, you’re probably not tied to the elephants. It’s just a thought. It’s just an idea. I say all the time and emotion, a thought after 90 seconds, we have a choice. We have a choice. So either you hold onto it and keep it a part of your reality, even though you’re not tied. Or you can choose to let it go. And then really starting to carve out that time to be present, to listen what’s inside. Whether you’re a head hard or a gut person, doesn’t matter. Listen. What is coming out? What is the craziest thing that is sitting inside of you? And it’s okay. It’s just an idea. It doesn’t mean you have to do all the things. But recognising that, indeed, you do have that choice. And so a little choice, one degree shift, changes that massive ship. So even if you make that one degree shift, every single day of shifting towards more of that extreme idea, it can happen. And slowly, those elephants will shift away and the rains will fall and you can do it. There’s many of us that have done it, as extreme as it is, build that personal board. And there’s plenty of people around you that want to support you and give you that freedom to be who you are.
Anna: I love that. Thank you so much, Jen. It was such a pleasure to talk to you finally, I was so happy to be able to share your story. And again, the idea of the personal board and the elephant training metaphor, I think has a really powerful visual representation of what a lot of us experience. Where can people find out more about you and connect with you?
Jen: So happy to connect to whatever really social media platform you love. I’m really active on LinkedIn. My name’s Jennifer Hill or JHcoachingconsulting.com, is my website. Happy to have a free connection call with you if you’re interested in coaching or just want to chat more. I’m always open to connect or send me a direct message. Coach Jen Hill on Instagram. And I’m on Twitter as well. And yes I am on Clubhouse. Occasionally. It just depends.
Anna: I’m still there, I have my profile, just I’m not doing the weekly session I was doing before.
Anna: And I think, yeah, for now, I’ve de-prioritised it in my strategy with the limited time I have with my little ones as well. But again, I’m grateful for the connections that it allowed me to make, at least at the time, whatever happens in the future. But I’ll be sure to link to your website and to all those social links as well. So thank you again, Jennifer Hill, for sharing your insights. Thank you for sharing your story.
Jen: Thank you.
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