Should I Go Self-Employed? What to Consider Before You Take the Leap

Blog categories

business-792176_1280

Dr Denise Taylor

19 September 2025

Share

When you’ve been job hunting without success, or find yourself disillusioned with employed roles, the thought of self-employment can be enticing. You imagine setting your own hours, working from home, following your passions, and being free from office politics. For some, it’s exactly the right move. But for others, it’s a decision that brings more stress than freedom.

Before jumping in, it’s important to understand what self-employment really involves, and whether it’s the right fit for your personality, skills, and lifestyle.

Let’s start with the positives. Self-employment can offer a huge sense of autonomy. You choose what you work on, who you work with, and how you spend your time. There’s flexibility, no need to ask permission for holidays or feel guilty about taking a sick day. If you’ve got a strong interest or expertise, you can build something meaningful around it. There’s also the potential for higher income, especially if you establish a niche offering.

But then come the realities. You don’t get paid holiday. You don’t get sick pay. You don’t have colleagues to bounce ideas off or managers to set direction. You are all departments: marketing, finance, admin, customer service, delivery. And unless you already have clients lined up, you’ll need to market yourself, pitch for work, and build a reputation from the ground up.

Many people underestimate just how much time and energy goes into finding clients or customers. Doing the work is only part of it. You’ll need to constantly think ahead, keep up visibility, and manage cash flow carefully, especially in the early months.

It’s also worth asking yourself: do you want to turn your current idea into a business, or are you just looking for a way out of your current job search frustration? Self-employment can be incredibly rewarding, but it needs to be chosen consciously, not as a last resort.

Here are a few questions to reflect on:

  • Do I have a clear offer that people are willing to pay for?
  • Do I enjoy working alone—or do I thrive on collaboration?
  • How comfortable am I with uncertainty?
  • Can I manage fluctuating income, and do I have savings to fall back on in lean periods?
  • Am I ready to keep learning, adapting, and self-motivating?

For some people, these answers will be a strong yes, and self-employment will feel energising. For others, it may be wiser to explore flexible employment, portfolio careers, or part-time roles that offer more balance.

There’s no shame in deciding it’s not for you. And equally, no harm in giving it a try, if you do so with your eyes wide open.

Start small. Test your idea. Talk to people who’ve done it. Know that it’s okay to change your mind. What matters is that the choice is informed—and yours.

Share

Related career coaching blog articles

ecology-2985781_1280

5 September 2025

Should You Turn Your Hobby into a Business? The Dream, and the Reality

startup-593341_1280

24 January 2024

Nervous To Launch Your Own Business? Here’s Some Top Tips To Help You Get Started

keys-1380134_1280

8 December 2023

Key Considerations for Aspiring Trades Business Owners in the UK