Finding Work that Fits: Choosing a Career When Everything Feels Shaky

Hey friend, welcome back to Wild Rose Pages, come settle in.

Today I want to talk honestly about something that’s taken up most of my year: trying to figure out a career that actually fits me. Not just something that pays the bills, but something that feels like mine.

This one’s a long, messy, real one. I’m going to talk about my history with jobs, what I learned from a career coach, the awkward middle ground of needing money while building something new, and what I’m doing next. If you’ve ever felt stuck between working to live and living to work, this episode may be helpful to you.....

My job history and the problem

I’ve done a lot of different jobs: busser, barista, working in retail, greenhouse worker, office manager, bookkeeping. Some of them I liked more than others. None of them felt like the thing that called to me.

For a long time I thought the goal was to find a steady, “safe” job and stick with it. But I’ve been changing. My interests and energy have shifted. The bookkeeping I used to do was fueled by wanting to be helpful (maybe to prove something) but that motivation faded. When the fuel is gone, the job turns into something that drains you.

I realized part of the problem is that my life is constantly changing. I need flexibility and variety. I get restless with rigid schedules. That makes traditional 9-to-5s feel harder to fit into my life.

What helped: a career coach and the checklist

A career coach I found on TikTok helped me in a surprisingly practical way. We went through questions like:

What tasks actually give me energy?

What drains me?

Which skills do I want to carry forward?

What environment do I thrive in?

Three important things I learned:

1. It’s okay to change jobs. Growing people change their work and that’s fine.

2. You can design a path that’s in stages: short-term “bridge” jobs that support longer-term dreams.

3. You can build a compass that can help decide if a job aligns with you.

That framework helped me reframe things. Find my skills, the kind of job I want, networking tips, and more. So instead of panic or shame, I'm starting to see my path as multi-layered: jobs that pay the bills, jobs that build skills, and projects that feed my soul.

The messy truth: bridge jobs, side projects, and burnout

Right now, I’m juggling four things:

1. Making content (blogs, videos, podcast episodes).

2. Building my own business (virtual assistant services aimed at herbal/wellness creatives).

3. Studying Herbalism with homework and classes to attend.

4.Working to keep the bills paid.

I thought being a virtual assistant could be my main bridge toward the life I want. It still can be but starting an online business takes time, and while that grows…. I still need income. That’s where the “bridge job for my bridge job” thing comes in,  the reality is frustrating! It’s a lot.....

Applying for jobs can also mess with your self-esteem. I feel like job market sucks right now. I finally found a part-time event coordinator role that seems flexible and connected to my interests (planning and coordinating events) but the schedule became wild: split shifts, early mornings and late evenings. That made me stressed about my puppy, Poppy, and drained my energy. I found myself wondering: am I being weak? Should I just suck it up because they trained me? Or is quitting the right move to protect my mental health and priorities?

Spoiler: There aren’t neat right answers. 

What I’m learning and small, practical steps I’m taking

If you’re in this same in-between place, here are a few practical things that helped (or are helping me)

1. Make a “priority map.” Write the three things you need to keep moving forward (money, skill-building, creative work). Assign realistic weekly time blocks to each. Small and consistent beats, Small wins keep you going!

2. Treat bridge jobs as experiments. Decide before you start how long you’ll try a role and what would make you leave (schedule chaos, no skill growth, too much stress). That's when the career compass came in. 

3. Be honest with your energy. If a job schedule is consistently harming your mental health, it’s okay to rethink it. You can be grateful for what you learned and still move on.

4. Ask for help. Tiny supports make big differences.

A message about compassion and life design

I want to be gentle about this. If you’re switching careers or trying to build something new while paying bills, you’re not lazy. You’re navigating complexity. The system asks us to pick one path, but people change. Our work can and should evolve with who we are.

For me, the goal isn’t to center my whole life on a job. I want variety, creativity, and freedom. I also want security. That combination might feel contradictory, but it’s possible with small experiments, bridge jobs that teach skills, and a long-game approach to building income from creative work. And I’m saying this as a 24 year old who is currently living at home, which comes with its pros and cons. I know everyone’s situation is different, and this career stuff may not apply to you but I hope in sharing my experience it could help someone.

Thanks for listening and being here with me while I figure this out. If you’ve been through a career pivot, I’d love to hear what worked for you; drop a comment, DM me, or even email me!  If you’re curious about virtual assistant work or need help mapping baby steps for a creative business, I can share what I’m learning!

If this resonated, save this episode/post, share it with a friend who’s also navigating job changes, and let’s keep this conversation going.

Until next time, be kind to your energy. Be patient with the process. And remember you’re allowed to change!

Sending warmth from my little corner to yours, see you soon!

~ Rosie