From software sales to financial advising
Jimmy decided to challenge some limiting beliefs about changing careers after 30. Then he swapped following negative online commentary for real-life career change conversations.
The result? He transitioned successfully into a career he'd always been curious about.
What sparked your career change?
Losing my job in tech in mid-2024 was the spark that I needed to get serious about a change. In truth, I'd been laid off 3 times in the space of 3 years, always under pretty ruthless circumstances. This experience was highly stressful and left me feeling very disillusioned about the tech industry I was working in.
What work were you doing previously?
I worked in software sales for about 7 years.
What are you doing now?
I am working in the financial advice industry. I am currently working for a boutique advisory firm with the goal of becoming a registered financial advisor.
Why did you want to change?
Deep down, I knew I wouldn't be in software sales forever. I'm in my mid-30s, and it certainly felt like the time to do some serious thinking about what I wanted to do in the long term.
I'd been very passionate about investing for close to 10 years. And although I worked in software sales, I was always more interested in reading and learning about investing than I was in software.
But for various reasons, I'd been hesitant to consider a career in the finance sector.
And, as I mentioned before, I'd been put through the ringer working for some hard-nosed software companies.
What process did you go through to make the decision to change?
Working through Jo's program helped me reflect on my values and what I really wanted in a career. Some things that stood out to me were:
Doing something that I found interesting and mentally stimulating.
Being able to help people.
Having work-life balance so that I could do the things outside of work that I enjoy - exercise, travel, hobbies, etc.
Developing a potential pathway to entrepreneurship/ business ownership.
Honestly, before starting Jo's program, I’d felt really lost. Time was passing, and I was struggling to make a change.
Every time I'd have an idea about a new career, I'd get super excited for a day, and then part of my brain would go into overdrive, coming up with every possible reason why it wouldn't or couldn't work, and I'd get pessimistic. I had many sleepless nights!
The first few weeks of Jo's program were quite introspective, helping me understand my values and what I want from a career. They were also quite helpful in helping me work past some of the unhelpful limiting beliefs that were holding me back.
Next, the program focused more on trying to pinpoint careers that were a good fit for my interests and values. Then I started reaching out to people in those fields for perspective on what it might be like for me.
What was the hardest part of changing careers?
Working through the mental barriers I kept creating for myself!
I'd been put off considering a career change into financial advice based on reading negative commentary about it, mostly on Reddit threads.
Jo encouraged me to ignore the negativity online and start talking to actual people working in the industry to get a genuine perspective on what working in financial advice was like.
This was a valuable lesson. Because for me, it turned out that the Reddit threads for EVERY INDUSTRY were overwhelmingly and misleadingly negative!
I've also taken a pay cut – but in the long term, I am confident that I can rebuild my income and surpass what it was in my previous job.
Finally, moving into financial advice has meant I’ve had to do some study. Initially, I was a bit reluctant to do this, but now that I've started, I'm enjoying it. It's empowering to know that I’m still very capable of learning new things and skills. The time commitment is challenging at times, but I'll get through it and be in a better position for having done it!
How did you go about making the shift?
Working through Jo's program and talking to people in the industry, I decided to join.
The Financial Advice Association of Australia's website led me to some articles about other people who had made career changes into the industry in their 30s. I reached out to these people on LinkedIn, and to my surprise, they were very happy to discuss their positive experience working in financial advice with me over the phone.
This was a game changer - getting an honest perspective from people working in the industry rather than relying on the nonsense on Reddit!
Serendipitously, these conversations led to my first job offer in the industry, which I hadn't expected at all.
What help did you get?
Jo was very supportive throughout the program. I really appreciated her flexibility during a period where I needed to press pause for a few weeks to attend to some other life circumstances.
What have you learnt in the process?
Many of the barriers to changing careers are ones that we make for ourselves. With the right mindset, we are capable of a lot more than we initially think.
My three biggest takeaways from Jo's program were:
The value of reflecting on what you actually want to do or what you might enjoy as a career. I think many of us stumble into random careers after uni. Then, after a few years, we feel trapped there.
Put yourself out there and talk to people working in the field you’re interested in. It can take a bit of courage, but it's well worth it! I was so pleasantly surprised by how willing people in the financial advice industry have been to have a conversation with me and let me pick their brains. At the end of the day, I think people genuinely enjoy helping others!
Ignore the stuff you read online - most of it is overly negative and written by people who aren't speaking from personal experience. I found this to be the case for every industry or line of work that I researched online before speaking with real people.
How are you feeling about the change now?
Overall, pretty good. There's been a steep learning curve, but it's better than feeling lost and paralysed, which was how I felt before starting Jo's program.
I’m enjoying being able to help people while applying a lot of my knowledge around investments and the markets.
What do you miss and what don't you miss from your previous career?
I occasionally miss the elated feeling of closing deals and bringing in revenue (+ the commissions) in my previous career in software sales.
I don't miss being forced into being a high-pressure salesman and the stress that comes with that.
What do you wish you'd done differently?
Honestly, I wish I'd made the change out of tech sales a few years earlier.
What 3 tips would you give others in the same situation?
If you're feeling utterly lost and stuck in your career, I'd recommend having a chat with Jo.
Go easy on yourself – changing careers can be a daunting process. You're not alone – many people go through this.
The best way to get a genuine perspective on what working in each job or industry is to talk to people who are doing it. Avoid the trap of relying on Reddit and other forums – they tend to be full of negativity that doesn't represent reality.
Hi, I’m Jo Green, a Career Change Coach.
I help thoughtful professionals who feel stuck or unfulfilled in their work find a clearer direction and move into work that feels meaningful and aligned with who they are.
Since 2016 I’ve supported hundreds of people to reshape their careers – whether that means changing roles, starting something new, or finding work that contributes more positively to people or the planet.
If you're thinking about a career change and want structured support, you can learn more about my career change coaching here.
Or you’re welcome to book a free 20-minute consultation to talk about where you’re at and whether coaching could help.
