When the Grass Looks Greener: How to Survive the Self-Employment Struggle
- janesteen100
- Apr 9
- 2 min read
Updated: Apr 11
By Dawn Roberts, principal trainer
Being your own boss sounds like a dream—until reality slaps you in the face with tax returns, tricky clients, and the soul-destroying question, 'So, what do you actually do for a living?' Suddenly, that 9-to-5 gig with paid holidays and a predictable salary starts looking mighty appealing. Maybe, just maybe, it's time to dust off the old CV and see what Indeed has to offer...
Stuck Between Business and the Job Hunt?
One minute, you're fired up about your business; the next, you're daydreaming about an office with free coffee and a steady salary. If you’ve ever hovered between 'I’m building an empire' and 'I wonder if that company has private medical insurance?' you’re not alone. Running a business is tough, and it's easy to question if the struggle is worth it. But bouncing between self-employment and job hunting can create more stress than either option on its own.
Why the 'Foot in Both Camps' Approach Doesn’t Work
Splitting your energy between your business and job searches means neither gets your full attention. You’re in a constant state of 'what if,' making it impossible to commit to anything fully. It’s like dating two people at once—sounds exciting, but mostly it’s just exhausting.
Instead of half-heartedly chasing job security while half-heartedly running your business, try these strategies:
Get Clear on Your Why – Why did you start your business in the first place? If it was for freedom, control, or passion, remember that before throwing in the towel.
Identify the Real Pain Point – Are you struggling because business is slow, or are you just feeling overwhelmed? Fix the actual problem instead of seeking an escape.
Give Yourself a Deadline – Instead of endlessly flirting with employment, commit to your business for a set period (say, six months) and go all in. If it still doesn’t work, then re-evaluate.
Surround Yourself with Support – Business is lonely, but it doesn’t have to be. Find a group, or community that helps you stay motivated and focused.
Activity: Commit or Quit?
Write down three reasons why you started your business
List the top three struggles making you doubt your path
Identify one immediate action you can take to address each struggle
Set a commitment deadline—how long will you give your business before reconsidering?
Call to Action: Get Off the Fence and Get Support
Running a business is hard—but doing it alone makes it even harder. If you’re tired of second-guessing your decisions and need real support, join our membership today. Get expert advice, accountability, and a community that understands the highs and lows of self-employment.
