Take a Break to Move Forward with Roshida Dowe – High Powered Lawyer Turned Career Break Coach

Roshida Dowe had climbed the ladder, she “made it” in the eyes of pretty much everyone, from a financial perspective, and yet it wasn’t what she wanted. So she took a year off and hasn’t looked back. Now she helps other people do the same, stepping into a break as a way of moving forward, […]

Roshida Dowe had climbed the ladder, she “made it” in the eyes of pretty much everyone, from a financial perspective, and yet it wasn’t what she wanted. So she took a year off and hasn’t looked back. Now she helps other people do the same, stepping into a break as a way of moving forward, it’s inspiring and worth a listen!

Roshida’s Website: https://www.shidasontheloose.com/

Episode Transcript

Josh Haynam:
Hi everyone. This week, we are here with Roshida Dowe. She is a career break coach who hit a point in her corporate job, her corporate life, where she realized that she needed a break and financially that was possible. So she set off to find some answers for herself and is now making a career out of helping other people who are in that same place, do the same thing. So thanks for coming on, Roshida.

Roshida Dowe:
Thanks for having me, Josh.

Josh Haynam:
So I want to start actually closer to the beginning because I think from my perspective being where I am now, this can feel a little inaccessible. Okay, somebody who reached a point in their career where they can take a break, that’s not me. So let’s start further back. How did you get to that place in the first place, in terms of your career, reaching this point where you could actually take a break?

Roshida Dowe:
So I am a lawyer. I practiced corporate law for a long time, for 14 years. That’s not right, 12 years before I… I don’t want to say I washed out, because that sounds like I couldn’t hack it, but I, spiritually I’ll say, washed out and said, I don’t want to do this anymore. But I want to go back on something you said, you said it feels inaccessible. And one of the things that I was surprised at when I started looking at this as an idea for myself in my own life, was how accessible it really is. And that the idea of inaccessibility is something that is often placed in our minds by fear and often placed in our minds by the conditioning we get in a society that expects you to work until your body’s just a shell and you can’t do all the fun things you want to do anymore.

Roshida Dowe:
So, when I set up for my career break, I knew I wanted to travel for a year. I was working at a company that went out of business. And so I had been paid a significant enough severance that I wasn’t worried about money. And I knew I could go at least a year without worrying about money and about without budgeting. Now I’m a bit of a frugal traveler. So I… it’s not five star hotels every night, but I also didn’t stay in hostels. I was just… finding the thing that felt good for me in whatever town I’m in, regardless of the budget, was my travel style. But along the way, I’ve met a lot of other people who’ve done this too. One of my now close friends did this starting in, I think 2016. And she traveled for an entire year for $14,000.

Roshida Dowe:
So that’s one of the things I point to when we talk about who can do it. Yes, the idea of leaving your job behind is hard. The idea of traveling the world, of no longer having the safety net of all of the things you built into your daily life, leaving that is hard. But if you don’t love it, if every day you’re not lighting up about the life you go get to live, then isn’t that life a little hard too? So to me, it was just a trade off of, yes, I can continue to work here. I’m in the Bay area. I love it here. I could get another job working for another company or I could see what life has to offer.

Roshida Dowe:
And for me, I’ve been thinking about taking a career break, I think since the first time I realized people did it. And I remember seeing a young woman from the UK who would work for six months at a coffee shop and then travel for six months. And I was like, wait a minute. I’m a responsible lawyer, fiscally responsible. I can’t just take off for six months at a time. And with the idea that I wouldn’t be able to afford it, so how can she. And then I realized that was all bullshit.

Roshida Dowe:
First of all, I shouldn’t worry about how she’s doing what she’s doing. And second of all, I can afford it. And a lot more people can afford it than actually think they can. Your career break doesn’t have to be a year long. It could be six months. It could be six months in one country. Six months in Chiang Mai Thailand isn’t going to cost you that much. But if that six months away from what has been a very stressful life, if that’s six months away from a job that has you hating to wake up every day, isn’t that six months you deserve? If you could make it happen anyway, if there’s any way at all that you can get it together and exit the thing you don’t like and give yourself a chance to start over. Don’t you deserve that break? Whether you come back in a year or in a year you decide you want to do something else. I love to tell people that they deserve that break, to decide what they want next.

Josh Haynam:
Hmm. Yeah. I mean that is quite convincing and it makes a lot of sense. For you personally, in your story, in your journey, how did you get to the realization that that’s what you wanted? How did you finally, the business went out of business that you were working for, but apart from that, how did you decide for yourself that that’s what you wanted to do?

Roshida Dowe:
I started applying for jobs and I did not want any of the jobs I was applying for. And I was applying for jobs just to have a job. Because that’s what you do. You lose a job or you quit a job or something happens, you go get another job. That is what is ingrained in us as Americans. You had a job, you don’t have a job anymore. So you go get another job. And anything else is like, “Whoa, what are you doing?” And I had been seeing a therapist at the time because of my coworkers. And I was talking to her about the fact that I didn’t want to get another job, then I had told her, I think I mentioned to her, but I’d rather just travel the world. And she was like, “So why don’t you?”

Roshida Dowe:
And I think that was the day I went home and I looked at my savings and even without the severance pay, I was like, “Oh yeah, why don’t I?” I’ve been saving money for a long time. Why wouldn’t I do that? And then I went back to her a couple of weeks later and it was like, “No, I think I’m just going to get a job. And I’m going to save for…” because between the time we were having this conversation and my job actually ending was like a month period. So I was making this decision and then having to push the button in a month. So I was like, “Yeah, no, I don’t want to, I’m just going to work for a year, get a job. Something I don’t love, going to work there for a year and I’ll save money and I’ll make plans and then I’ll go.” And she laughed in my face.

Roshida Dowe:
She was like, “If you don’t go now, you’re never going to go.” I didn’t really fully get it at the time but there was nothing standing in my way besides fear. And I was still putting up roadblocks. I was still telling myself now isn’t the time. Okay, let me explain to you why it was the exact perfect time. So my job ended on April 27, 2018. My lease was up for renewal on May 8th, and May 1st I was taking a trip to China that I had already been planned before the whole company going out of business thing.

Roshida Dowe:
And so I was going to be in the Bay area with a lease I either had to renew or move out of the place, and they were raising the rent of course, because why wouldn’t they? And it was like, do I want to commit to a $2,700 a month, one bedroom apartment when I don’t have a steady paycheck coming in, or could I take that money per month and see more of the world?

Roshida Dowe:
And then if I’m not… if I’m going to move because I no longer want to stay committed to this expensive apartment, which I could afford, it was great when I had a job. But if I want to move, because I hate moving, why not just put my stuff in storage and then go explore the world. So it really was a point in my life where I had to make a big change and my options were to… I love to travel, so my options were to follow the dream I’d had for a while, of seeing as much of the world as I can, or to do the status quo thing. Do the thing that my family would understand. All my friends would understand, which is get another apartment, get another job and go back to work.

Roshida Dowe:
And that was the moment where… that’s what it came down to. It came down to not just the job going away, but it came down to the decision of, I’m going to have to make a change in my living situation. I’m going to have to make a change in my job situation. I can either follow my dream or I can come up with excuses not to. And my therapist was like, stop coming up with excuses. So that’s really how I got there.

Josh Haynam:
Yeah. That gives a broader picture of it. Because I think the nebulous, or just cloudy part for a lot of people is like, “Well yeah, but what did it look like practically?” And I think that gives a much better picture of what the actual practical situation was. So thanks for letting us in on that. So what happened when you went on this year? Did it actually, what changed, what shifted in you and what made you realize that you wanted to spend significant time, because it’s been over two years now that you’ve been a career break coach. What made you decide that this is so important that I want to help other people make this jump?

Roshida Dowe:
It’s two things. First is, I don’t ever want to have to clock into somebody else’s job if I don’t have to. Like Josh, if you hear that Roshida Dowe has a job, it’s either something that I have created that I love so much, and I’m super excited about it, or it’s desperation. Honestly, that’s where I am right now. And I hope I don’t, and this is not going to be the same for everybody, but because of my year experience, for me, I know I don’t… the part of my job I didn’t enjoy was the part that involved other human beings. And I’m a people person. I love people. But I had a lot of bad bosses. I had a lot of bad clients. I’m not interested in doing that for money anymore. I don’t… I’d rather spend my days doing things that satisfy me. So the idea that… how do I put this? I think I’ve lost your question, Josh. We may need to…

Josh Haynam:
So yeah, that paints the picture of why it’s so important for you. What made you realize that this is what you wanted to make a career out of moving forward or not even a career per se, but just a livelihood?

Roshida Dowe:
Okay. On my career break, I kept getting comments and notes from other women who would say things like, I wish I could do this too. But then I also found other women who had done it. And so a lot of what I do and a lot of what made me realize this was a possibility is that connecting that, what is it that makes you think you cannot do it? Woman who’s contacting me saying she, that she wishes she could. And maybe this woman’s story, this woman who’s done it will help you. If my story won’t, if I don’t resonate with you, maybe this other person will.

Roshida Dowe:
And then a lot of it is sort of helping people along the way with the more technical aspects of choosing where to go and how to do certain things. I never thought it would be a career, but it’s the thing people always ask me about, like, “How did you do that? I’d love to do it. How did you do that? I’d love to do it.” Eventually it just turned into coaching. If that thing that you get asked about is probably, it’s a good place to start when you’re looking to make some money or looking to do something. So yeah, the picking my brain turned into a more formal coaching session.

Josh Haynam:
Yeah. That’s a very good place to start. Someone is proactively asking you, then there’s got to be other people that also have the same questions. So you have these questions coming in. How did you then take that and start charging people?

Roshida Dowe:
So I did pre coaching for a while, maybe six months or so. And then eventually I realized that it wasn’t sustainable in the sense that I have a website to pay for. And the reason people can schedule pre coaching with me is because I have a scheduling program. So somebody’s got to pay for it, and it can’t always be me paying for the resources to help other people. So it took me a while and I’m glad it did because it really gave me a lot of experience in what these women were looking for. And so it’s made me a better coach, but yeah, and I don’t know how I would have felt charging for it right away, but doing it for free for about six months gave me a better idea of what people are looking for. It actually helped me create courses.

Roshida Dowe:
So I have a couple of courses to help people walk down this path. And most of that is based on questions I get in coaching and also my own experience. I like to teach a lot from the mistakes I made because I made a bunch. I made a bunch of mistakes. And so it was great to be able to sit back now and say, “Okay, I hear you. I see what you want to do. Let’s walk through your plan or what your plan looks like and don’t do X because I did, and it was silly kind of thing.

Josh Haynam:
Hmm. Yeah. That’s a very good place to get the answers to the questions is your own mistakes. A question that I find fascinating, who was the first person that you charged for coaching and how did you feel on that call?

Roshida Dowe:
I listened to an episode of your podcast last night right before bed. And you asked someone that, and I [inaudible 00:17:04] thought, I hope he doesn’t ask me because I have no idea who it is. But here we go. Honestly, I don’t know who the first person is because it went so seamlessly from unpaid to paid. I didn’t do any advertising. I had a weekly newsletter and I consistently mentioned the coaching and all I did was take off the word free. And in the back end there was a number. And so, I don’t know who the first person was, but it didn’t phase them that it was a paid session. So, yay.

Josh Haynam:
Yeah. And it sounds like because you had those six months of run-up and you knew… I’m guessing that you knew this was valuable, people were probably telling you this is really helpful to me, that probably made it feel a lot less difficult to put a price tag on it.

Roshida Dowe:
My clients get results. I have no doubt that it is valuable. Where, as a business owner, where I have doubts is will I have enough clients for this to be a longterm proposition? Because it’s often not the kind of thing you think about unless someone guides you to the idea. But every… I can’t think of a single woman I’ve spoken to who didn’t get her desired end result. Sometimes it’s like, “I talked to you and I quit my job within the next two weeks.” Last week it was, “I quit my job within two days talking to you.” Which, my goal isn’t to make people quit their jobs. I love it, but it’s not my goal.

Roshida Dowe:
But if that’s my client’s goal to get out of a toxic work environment and then figure out what comes next, I fully support them in that. And I’ll give them the tools to help them with that. So, yeah. When my client says, “I talked to you and then two days later I quit my job that she wasn’t planning on quitting at all, I get kind of excited about that. Like, “Okay, we’re making progress, we’re making progress.” And so yeah, this might not find… I don’t know what to expect from this financially. It’s never been something that has paid a lot. It is truly a passion project now. I like money.

Josh Haynam:
Yeah. And let’s talk about…

Roshida Dowe:
I like money.

Josh Haynam:
Yeah, so let’s talk about that.

Roshida Dowe:
I would like more money and that’s part of the reason that there are courses and there are other things, other products, but I like results as well. So.

Josh Haynam:
Yeah. So let’s talk about that because there’s a lot of people in this position where they don’t need to work for a while, but for you personally, how long are you willing to go before you want this new career as a coach to be providing in a way that allows you to live a certain lifestyle? How long are you willing to let it play out before you decide okay, “Now I really need this to actually let me live the way that I want to live.”

Roshida Dowe:
I’ve never thought about that before. In my mind, this might be really romantic and maybe it’s naive, I mentioned to you before that I consider myself retired. I don’t know that there’s an amount of time that I’m putting on career break coaching. I think I’m going to coach people about this formally or informally for the rest of my life. Am I going to make a living from it soon? I hope so, like a real living from it, I hope so. Do I know for sure? No. Am I willing to do it in some capacity without it being financially fruitful? Yes. So even if that’s… I’ve shut down the business, I’m no longer blogging and creating products, but a friend of a friend knows me so they can call me and talk to me about what they want their career break to look like, that might be what’s happening in seven years.

Roshida Dowe:
I don’t, that truly is something that changed my life. I think that’s what it is at its core. This opportunity and this experience changed my life and I’ve seen it be life changing for other people. And I want to help everyone I can experience this. And I’m not the greatest salesperson, and so I’m not always pitching my products the way I should or the way they could be, but if I’m reaching people and they are seeing results, that’s enough for me.

Josh Haynam:
Hmm. Well, I can tell you from my perspective, my coach, who I’ve been working with for six years now has the same approach where his life was changed by what he’s learned and now he really just wants to share it with other people. And from my perspective, and seeing tens of thousands of coaches now come through [inaudible 00:23:04], that really is the glue that holds it all together when things don’t go so well, or maybe it’s not replacing the salary and you have to do some other work for a while. But I think that as long as you actually care, it really can’t go wrong. So that’s pretty amazing.

Roshida Dowe:
Thank you. Yeah. I love seeing people light up when they talk about what their career breaks look like or could look like. It’s amazing to have people, because as a society, we are told to work, work, work, work, maybe take a vacation if you can get it approved and then work some more. At my last job I had unlimited vacations and I never took more of a two week vacation and my manager still happened to bitch at me about my vacation. And I’m like, “Is there work hat’s not done.? No.” Like, “Is there something that I was responsible for, but didn’t get done. No. But you just don’t like the looks of me being on vacation. Even though one of the perks of working here is unlimited vacation. There are so many ways that jobs… that a bad job can make you unhappy. Even if it has that great paycheck or some other perk, a bad job can truly make you really unhappy. And so I’m not signing up for any more bad jobs and I encourage people to opt out of bad jobs.

Josh Haynam:
Yep.

Roshida Dowe:
And I was talking to someone on a career break about returning and I love her quotes. And what she said to me was, I asked her if she was worried about getting another job. And she said, “No, I had a job I hated. I know that when I come back, I could find another job I’ll hate.” Like, “If I don’t love my job now, why am I worried about what’s going to be on the backend for me when I come back, I’d rather leave and experience life and then get another job I hate.

Josh Haynam:
Yep. Yeah. Well, this has been absolutely awesome. I feel like I’ve gotten to go on your journey with you. So thank you for just being open and sharing with us. I think one of the things that’s super interesting with podcasts like this is for anyone listening to be able to jump onto your journey where it is now and follow along. So if somebody wanted to do that, what’s the best place to see into your world and where things go from here?

Roshida Dowe:
My website is shidasontheloose.com and that is S-H-I-D-A-S-O-N-T-H-E-L-O-O-S-E.com. If I butchered that Josh, you’ve got to take that…

Josh Haynam:
I think that was right. I was following.

Roshida Dowe:
I was like salting my eyes and trying to picture out all the letters. Yeah, that’s a really good place to start and see what I do, what I offer, what my experiences have been. I love meeting new people. So come say, hi, leave a message. Make sure it’s a nice message. We only do nice messages. Thank you. Yeah, that’s it.

Josh Haynam:
Awesome. Well thank you for coming on. Really appreciate it. And just thank you for being open about your story.

Roshida Dowe:
Thank you, Josh. Thanks for having me.

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Josh Haynam

Josh Haynam is the co-founder of Interact, a place for creating beautiful and engaging quizzes that generate email leads. Outside of Interact Josh is an outdoor enthusiast, is very into health/fitness, and enjoys spending time with his community in San Francisco.

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