“I could feel myself starting to check out.”
What work were you doing previously?
I was working in finance, specifically investment banking.
It was a typical rat-race role, with crazy hours.
What are you doing now?
I run my own business, called The Soloist: it's all about solo travel.
I offer one-on-one travel planning services for people. Perhaps they're interested in the idea of solo travel, but are a little scared or want someone to walk them through the process, or maybe they have no time to plan trips – I help plan trips for them.
I host small-group retreats for solo travellers or friends, who can come together, meet other people and do some fun activities.
Then I also have a blog which offers resources around solo travel and travel in general.
How did you feel in your work before you decided to make the change?
I went through different phases.
There were many years when I really enjoyed it. I felt challenged by it. I was surrounded by a lot of smart people, and I felt like the work I was doing was important.
Then I started getting older, and very senior in my career. I realised, "Wow, this is my forever".
It felt like a decision point was coming: either I needed to put all my energy into becoming an M.D., which was pretty much the most senior level, or, if I didn’t want to do that, then why was I putting all my energy into the job? It needed to be worth it. And I'd started feeling that perhaps it wasn't.
I also started feeling burnt out. I'd been in the industry many years, and I could feel myself starting to check out.
Why did you change?
That last year, the headspace I was in changed.
I looked at all my bosses, and thought about whether I wanted my life to be like theirs.
I wasn't feeling motivated, or like the work I was doing was really aligned with what I wanted to be doing. I wanted to be helping people more, but what I was actually helping was corporate greed.
When was the moment you decided to make the change?
I knew for sure that I was unhappy for at least the first six months of my final year there.
But I also felt trapped, and I didn't understand how I could truly get out of it.
Then I had this moment of realisation while on a retreat I went on.
I was surrounded by other women who'd started their own businesses – I met a woman who'd started her own nutrition coaching company, and another couple of women who'd started a dance studio. It was just eye-opening. I thought, "Wow, how cool is that? They just followed their passion, and clearly they’re making it work".
I'd known people who'd started their own businesses before, but for me that was the moment when I saw people doing other things who looked way happier than I felt. I knew I was miserable with my work, and while I didn’t know exactly what I wanted to do, I decided "I’m not doing this job anymore".
I realised I’d been working all this time, saving up all this money (which is the benefit of that career), but what was I saving for? While I’d felt like I’d been living in a prison, I'd actually had the keys the whole time – I could just quit.
So when I got back from the retreat, I started to put the process in motion – I would break my lease, quit my job after receiving my end-of-year bonus, and I would travel. After all, why not?
At that point I was still so wrapped up in the finance world that I thought maybe I'd go back to banking after some time off. Maybe I was just burnt out, needing to reignite that passion I'd had for it years ago. I knew that I needed a break to see it more clearly, and to see if I missed it or not.
I quickly realised after quitting that I was definitely not going back!
How did you choose your new career?
While in my old job, it was hard to even think about other ideas.
I was in this bubble, where everyone around me was in finance. It felt like my only exit opportunities were another bank, private equity, or some sort of credit or hedge fund. I couldn't even see the wider world.
And I didn't have the time. Most of my time was spent on my job. Any outside windows of time I had, I just needed to have fun, decompress. I needed to truly break away from it all to have that time and space to get clarity.
After I quit, I did a lot of soul-searching, which I think was necessary for me. It took time. What did I enjoy? What gave me purpose? I knew that it wasn’t the corporate structure anymore. I knew that I wanted to be helping people. I’d always enjoyed volunteering and helping my friends with different things. So I knew I wanted to do something connected to individual people.
I had a tiny seed of an idea in the back of my head where I kept thinking about solo travel, because it had truly changed my life. It gave me so much confidence. After my first solo trip I felt like I could do anything in the world, I was so empowered. And it gave me a solid sense of identity – I started to know myself a bit better.
I remember getting back from trips and my friends would say things like, "So you just went to Patagonia alone? That’s insane!" They were so shocked by it, and I’d tell them how I'd had the best, most life-changing time. I didn't want them to be scared; I wanted them to have the same experience.
That kept coming back to me – how much I wanted to share that with other people. I felt like they were the only ones stopping themselves, and if I'd had someone for that first trip to say "I’ve done this before, you’ll be fine; let me help you through it", it would've made it so much easier.
So I started to think about how I could actually monetise the idea.
Are you happy with the change?
Yes – 100%.
I feel like my business is only just getting started. Because I started it during the pandemic, it's been pretty challenging to convince anyone to travel abroad, but it’s starting and I'm definitely happy.
Regardless of what happens next, no part of me will regret this decision. I feel like if it doesn’t work out, whatever I do as the following chapter will be much more aligned with what I need and want, because I've gone through this whole process.
What do you miss and what don't you miss?
I miss some of the people, whom I still keep in contact with.
I made a lot of lifelong friends, as I was there for so long. I also miss some of the energy that comes with being so busy and feeling like you’re needed for a project.
I don’t miss corporate politics, which was something I always felt uncomfortable with. It never suited my personality. I just wanted my work to speak for itself. The more senior I got, the more I discovered the amount of political strategy involved. So I don’t miss that.
I felt like I didn't have a lot of control over my work–life balance. It didn’t matter if I was on vacation with my family – if I was needed, I had to drop everything and do the work, otherwise I was seriously at risk of getting a poor review, or even fired. So I don’t miss those demands on my time.
And I don’t miss having somebody else judge the quality of my work. I was always at the mercy of my reviews, my promotions – everything was at the mercy of someone else.
That started to bother me the more senior I got. I wanted to be valued by the client appreciating me (or not) directly, rather than having someone else in the mix judging it.
How did you go about making the shift?
I didn’t do what you’re supposed to do, which is to write a business plan!
But I feel like there’s no right answer and you have to do what works for you. For me, what was right was to tiptoe into it, little by little.
It actually started when a travel blogger I follow put out a post asking for people to contribute to her blog. I didn’t know why, but I felt called to do that, though I’d never written a blog post before.
I wrote it and thought "That was actually pretty easy. Maybe I should start thinking about having my own blog."
So I decided to start a website. I taught myself through Squarespace how to build it, then the next logical step was to start an Instagram account to go with it, and then to start a blog on the site. Little by little, I got deeper into it.
Then someone approached me to suggest we do a retreat together, which I thought was a great idea, and that’s how I got into retreats.
Since then, I've inched my way further along and just made sure that each step felt like it was still aligned with my core mission.
How did you develop (or transfer) the skills you needed for your new role?
I thought about how I'd booked travel for myself but never for somebody else – taking their payment information, worrying about liability and insurance, etc. It was a rabbit hole that I needed to go down and get more educated on.
I needed to become a travel agent to understand how to professionally book travel for somebody else. In the US you can get an accreditation as a travel agent for different host agencies and programmes, so that’s what I did. I took some courses, and then dove right in offering my services.
What didn't go well? What wrong turns did you take?
I had to learn different digital skill sets – Instagram, making a website, SEO – all things I'd really had no exposure to.
I invested in some online courses – most of them were great, but some of them were expensive and proved to be not so great. I wasted money on some of them and should have done my due diligence, making sure I'd reap the benefits that I was hoping for.
How did you handle your finances to make your shift possible?
I did have substantial savings which I'm grateful to my last job for.
I'd already been setting savings aside to use for travel for a year out, so I’d saved quite a bit.
More recently I’ve started to get clients and there’s money coming in, which is helpful.
What was the most difficult thing about changing?
There were definitely a few months after I quit when I had something of an existential crisis.
I wasn't questioning what I’d done as such; it was more along the lines of, "I feel purposeless, I’m not contributing to society, I can’t just do nothing with my day." So I guess you could say that I was missing that sense of purpose from my job.
And it's been hugely challenging starting a travel company during the pandemic, as friends and family who'd asked me early on to help them with travel suddenly weren’t going to be travelling anymore.
That initial start-up phase has been difficult. It's only now that it feels like it's starting to get 'legs'.
What help did you get?
Support from friends and family.
They’ll say things like "I really like your Instagram page" or "I read your article and it really resonated with me", which keeps me going.
And there have been people who've been willing to give me a shot, like that blogger who let me write for them. That’s been helpful too.
What resources would you recommend to others?
Do your research – which I didn't!
Look and see who else is doing what you want to do, how they did it, how you can get help.
In terms of shifting into the travel space, I personally just researched ‘How do you book travel for people’, ‘How do you start your own travel company’ – things like that.
But candidly, I think it’s more important to learn by doing, for me at least. You can look up all the resources, but until you actually start doing it, you don't truly realise what you need to learn and do, or how to find your own path.
What have you learnt in the process?
I've learned how to surrender to the process.
For so many years I worked hard, I formed relationships with the right people, and I got results. I knew exactly what I needed to do to get my next promotion. It’s been challenging for me to transition to a life and world where I have no idea how I’m doing at any given moment – nobody’s scoring me.
I can’t control new clients coming in – I can put my best foot forward but I can't force anybody to book anything.
So I’m learning to trust that I’m doing what I’m supposed to be doing right now, that things will unfold naturally, and that I just need to be patient.
What would you advise others to do in the same situation?
If you know people who have quit to do something different, or who've even just changed to a different company, talk to them more about their shifts. Take advantage of that.
Listen to your gut. I was getting a lot of signs from my insides that my career was not working out and I ignored them for years. Even during the times when I was enjoying my job there was something in the back of my head that pinged "Do you really want to do this forever?" at me, and I pushed that to the side.
I think your intuition is your most valuable asset. You should be listening to it – it’s not speaking up for no reason. I wish I’d put more stock in that earlier.
The third thing is to have more confidence in yourself and your skill set – that you will land on your feet in some way – and take the leap.
I guarantee that even if you do go back to your old job – even if you run out of money – you’re not going to regret that time, because you needed it. You'll learn more about yourself through the process.
The hardest part is taking the leap, but everything starts falling into place after that.
To find out more about Jen's business, visit www.thesoloist.travel
What lessons could you take from Jen's story to use in your own career change? Let us know in the comments below.