“How Do I Overcome The Overwhelm Of Starting Out On My Own?”

Monique longs to swap her soulless job for a self-employed portfolio career. But daydreaming is a world away from reality. Where do you start with the logistics of working for yourself?

What's your career history and current job?

I'm a product manager for a software company.

I'm a digital nomad so I can work from anywhere but with the benefit of that work being for one company.

I fell into this job. The company found me via LinkedIn and saw I had a project consulting background.

I've never had much of a focus. I think it's because I love to do a lot different things and get bored easily.

How do you feel about your work?

I'm disenchanted with working in the corporate world.

The leadership is poor and there are no professional development opportunities.

Three years in and I'm not evolving. I haven't had any chances to learn anything new, so I'm just going through the motions.

I'm extremely demotivated. The corporate world just isn't for me. You get pigeonholed into one role, with one skill set, because it's not in a company's interests to develop you in another direction.

All I wake up thinking about is how I wish I could sit down in a café and work full time on my dream and vision rather than somebody else's.

If I could quit tomorrow, I would, but financially, that's just not realistic!

What would you like to be doing instead?

My vision would be to do multiple things.

I'd like to start a website design and branding business for small companies.

Ideally, I'd have a niche in health and wellness, building websites for coaching and mindfulness businesses, that kind of thing.

I'm deeply connected to how fitness can help people; fitness has always been a huge part of my life and a huge part of how I've transformed as a person.

I've been thinking about setting myself up as a personal trainer for a while. I'm taking the first step by getting my spin instruction certificate and plan to take others further on down the line.

If I go down this path I'd like to be able to take a holistic approach to health in general, so I've also looked at gaining some qualifications in nutrition.

I just don't see myself doing one thing and one thing alone!

My plan is to move to Bali in January next year for the first six months, that's really just to keep my expenses low and be around other entrepreneurs.

I can then start to build my vision there.

What’s the biggest obstacle in your way?

I'm overwhelmed by the practicalities of starting out on my own.

Right now, I have the security of having one employer who takes care of the all the practical stuff for me. How do I switch to a position where I'd have to do all of that myself?

It's those logistics that are proving to be the real stumbling block for me – paying taxes, finding clients, finding work, keeping myself afloat financially. I don't know where to start with any of that and that's scary.

The thought of quitting doesn't frighten me. I'm excited about doing that and starting my own thing.

But not only am I going to move towards being self-employed, I'm planning on doing lots of different things to what I do now.

How do I handle the logistics of working for myself?

And how do I overcome the overwhelm that comes with such a big change?

Can you help Monique?

  • Have you been in a similar situation, or are you in the same boat right now?
  • How do you think Monique could move her shift forwards?
  • Do you know anyone she could talk to?

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