What letting go of office dream taught me about business decision-making: Jen Workman

I know of many business leaders who tell a similar story - having had a ‘dream’ of what a successful business should look like, they adjust, pivot or sometimes take a step back.

It’s like a young person coming of age and understanding more about who they really are.

It’s something I see play out in my virtual administration business too. Some businesses have big plans and see outsourced help as a stepping stone to having a team of staff.

But over time they come to realise that the level they’re at suits them and outsourcing becomes part of their sustainable and long-term business plans.

A former client who has run a business for 14 years, finds herself returning to the workforce and will make the business a side hustle. She too thought she would grow her small team to become much bigger than it is, but is happy to downsize and try something new.

Though these situations sometimes occur due to circumstances, the ‘big dream’ can look much smaller than we think.

For me, success is more about the lifestyle my work affords me rather than size, and to some extent money.

Which is why I too have been exploring new avenues.

The VA business is still my main focus, but I’m allowing myself to redefine what my career might look like. Which brings me back to portfolio careers, something I’ve mentioned before.

At a time when we’re probably less defined by our careers than we ever have been, and when lifestyle is a key motivator for how and when we work, portfolio careers could become the norm.

If this is something you’re considering, I’ll share two things I’ve had to grapple with to get to this stage. Firstly, I had to let go. Let go of what I thought my business or career should look like to give myself space to explore new things. Just like I did when I let go of my office.

We may feel limited by others’ perceptions, especially if leaving a seemingly stable career or opportunity for one that’s perceived to be less secure, but the chances are, it’s our own limitations that are really holding us back.

It may be a perceived easier leap looking at a multi-career path as a self-employed person than an employee, after all, we learn to work simultaneously for different companies.

But it’s still easy to feel defined or hemmed in, especially when you’ve spent a lot of time promoting a brand and specific brand messages and telling yourself success looks like something specific.

Secondly, I’ve had to consider how I’ll mitigate the challenges of this route. This includes potential blurred boundaries, burnout, never feeling like you do one thing really well, never feeling like a valued team member and working more hours than you would if you only had one job or pursuit.

I’ve accepted there are some unknowns that will only become clearer with time, but a portfolio career does have to be thought through. It’s therefore worth thinking through the challenges before committing to this, especially in the early days.

Whatever professional route you’re pursuing, the chances are your path has taken you in a different direction to what you planned, even if only slightly, and this is certainly no bad thing.

Jen Workman is founder of Business Owl, a virtual administration business