Build your career like an entrepreneur

Life is rarely linear. Not least when it comes to our careers.

Gone are the jobs for life.

Now, it's about the life that work can give you.

In our group coaching program, Vision 20/20, many mid-life career changers seek to align what they do with who they are.

But it can still feel overwhelming to contemplate a big career change.

Can you learn to be more creative, courageous, and resourceful when it comes to pivoting your professional life?

To explore all of this and more, we were joined by Iesha Small.

She's a career pivot coach and seasoned communications professional who helps working-class and introverted professionals thrive.

Iesha has pursued her own squiggly career path, going from engineer to assistant headteacher to career-change champion.

Whether you're feeling stuck in your current role, scared to make a big change, or simply seeking more meaning and purpose in your work, you’ll find Iesha’s insights empowering and connecting.

This one’s for you if…

• You're looking for inspiration and practical advice on how to build your career in an entrepreneurial way.

• You're considering a career transition or pivot but feel uncertain about how to go about it.

• You struggle with confidence in putting yourself and your work out there.

• You're seeking a mindset shift from an "employee" mentality to an "entrepreneurial" approach to your career, even if you're not ready to quit your job.

Here are nine takeaways from the conversation:

1. We’re afraid of what we’ll lose

We often resist change because of all the bad things we fear will happen.

Iesha has been there. She was afraid of not being in work and that those around her would think less of her. But when her circumstances changed, she had a big realisation:

“If I can't do it now and I can't give it a go, all the things that I was worried about before .. they've already happened.”

It’s hard to believe when we’re battling the 3am gremlins, but liberation often waits for us on the other side of what we’re scared of.

2. Employee mindset vs an entrepreneur mindset

Just because you’re an entrepreneur doesn’t mean that you think like one. Iesha highlighted the following key differences:

“Employee mindset: looking at skills and then fitting yourself to the job description. Entrepreneur mindset: looking at the problems that you can solve.

Employee mindset: attaching your time to money. Entrepreneur: it's about the outcome, the deliverables.

Employee mindset: waiting to be told what it is that you need to be doing. Entrepreneur mindset: What's the problem that you're solving?”

3. Connection first, opportunities later

We can end up dismissing someone if their timing isn’t right to work with us. But building genuine relationships can create more chances and more opportunities further down the line.

“If someone might buy something now, cool. Maybe I can help them. They might not want to buy something now, cool. They know where to come.”

By practicing non-attachment, we can become a resource that others know they can trust and depend on in the future.

4. Build confidence by showing up regularly

Many of us resist posting regularly on social media. It’s why we’ve created a guide to posting on LinkedIn for just 7 days.

And yet, consistently putting yourself out there can help build your confidence and attract opportunities. 

Iesha started with an anonymous blog that grew into a multimedia project and an approach from a publisher. And now she uses LinkedIn daily.

“When I was off last year, I decided to write publicly every single day. I was testing my ideas. I could see what people responded to.”

Through showing up, she’s developed more confidence and created opportunities.

5. Think like an engineer

Engineers know that experimentation leads to new outcomes.

“People are worried about things not working and looking stupid. 

I've gone back to my engineering roots on this, and I just experiment now. And it makes it so much more fun.”

Thinking like an engineer means that iteration is a part of the process, not a sign of weakness.

6. Use social media as your laboratory

If we let go of the fear of looking stupid, we can use platforms to test ideas, see how they land, and use the feedback to iterate. 

“I use it to see if people are interested in something. And if people are interested, I do it.

And if they don't, I'm like, ‘Okay, that didn't work.’”

Iesha also cautions against worrying about the number of views, revealing that some of her narrower-reaching posts have led to conversations with the exact kind of people she wants to talk to.

7. Reframe your job as a benefactor

We tell people not to quit their job to start a new business, and Iesha agrees.

It can be tough to handle paid employment and build a new business side-by-side, but a shift in perspective can help.

“I got some of my clients to reframe their job as their benefactor, as one of their investors, because it's paying them to be able to do the other stuff they want to do. 

And they were like, ‘Oh, I hadn't thought about it like that.’”

8. Rethink your organisation as a partner

When we’re working for an employer, it’s right that we do a good job. But is the relationship equitable?

“If you are an employee in an organisation, consider it a partnership. That is how an entrepreneur would do something with another organisation, right? 

You want to get the best out of it for your partner, but you also want to get the best out of it for you.”

Seeing your work as a partnership helps you factor in your own needs - and encourages a more active, entrepreneurial mindset.

9. Build your own assets

Many of us have been there. We’ve poured time and creativity into an organisation, and when we’ve left, we’ve come away empty-handed.

This is why Iesha passionately believes in creating your own assets - items that are separate from those you create with or for your employer or clients. 

“I do a good job for my organisations, but I also have many personal assets now that are distinct from them, that are my own, and that allow me to get other jobs or to create opportunities.

If people take away one thing, I would say that's it.”

If you could create an asset - a course, template, or download - that reflects your skills and knowledge - what would it be?

Iesha's story shows how writing and sharing your work publicly can be a great tool for an emergent career path.

She’s used it to clarify her ideas, build an audience, and create “luck,” uncovering her most valuable skillsets and offerings along the way.

Do you want to nurture your entrepreneurial mindset? Join our community, dip your toes in with a Masterclass or dive into transformation at one of our life-changing events.

Notes

Many thanks to Iesha Small. Check out her website and sign up for her newsletter to follow her work.