Employee to Entrepreneur: 5 Tips for Transitioning from Your 9-5 to Entrepreneurship

There’s are moments in life, epiphanies, when we realize the status quo isn’t making us happy and something has to change. They can sneak up on you, building for months or even years, before you finally have a moment of perfect clarity and see something that should have been obvious for a while.

But sometimes, there’s no warning.

They hit you out of nowhere.

And once you’ve had that moment, there’s no going back.

One of these moments happened to me when I was working as a lawyer. I’d spent years building my career and following a certain path. I really thought I had the whole ‘work thing’ sorted. Until suddenly, I realized I wasn’t happy in my job.

And because I wasn’t content at work, I wasn’t happy in my life.

There was so much I wanted: happiness, freedom, love, but none of it was happening because the ‘work’ section of my life was totally out of alignment. What I was doing didn’t match what I wanted to be doing, and it was throwing everything else off-kilter.

Once I realized this, I knew it was time for a change.

But change is scary.

Super scary.

But it can be so goooood.

The First Stage Of Transition

When you come to one of these revelations and realize that you aren’t happy with your current life or career, the next challenge is to decide to do something about it.

Once you’ve set upon this course, you need to start working towards achieving it. The decision itself is the beginning of this, but the follow-through is committing yourself to a course of action.

You may have been in your current position for years and finally feel like it’s time to change.

Or you may have made a move that doesn’t feel right.

Either way, your life doesn’t have to feel this way. To make a life transition that’s capable of getting you out of the 9-5 grind and into a life of freedom, and transforming the way you feel, you need to gain momentum.

Momentum is what will take you from that first stage of deciding what you want, and committing to taking action, to actually realizing your dream career or life.

Follow these steps to start creating the momentum needed for your own transition...

Tip 1: Use Your Creativity

If you’re stuck in a 9-5 job and dreaming of a different way of working and living, the odds are what you’re considering doing is a big change.

This may just be in the place you work - doing roughly the same thing but from home and for yourself, rather than in an office for your boss.

But it could be something wildly different.

For me, it was shifting from the world of law to life as a coach.

Huuuuuuuge transition!

Look at it this way. Simply changing from one job to another, in which you do exactly the same thing, but for a new company, can be a big shift.

You don’t know the people, the business culture, their methods of doing things, or the rules. It can take a while to get into the swing of things, develop working relationships and friendships with people, and understand areas where you have room to be yourself, rather than rigidly sticking to the corporate game-plan.

Transitioning from a 9-5 to a job you have created for yourself is every bit as much of an upheaval as a simple job change would be, but it comes with a lot of other adjustments on top.

The odds are, one of the things motivating you to make the change is a desire to unleash your creative spirit. To break free from the somewhat analytical world of everyday work and embrace something a little more right-brained.

Even if your new career isn’t a creatively based enterprise, you’re still going to need to harness all the creative potential that has driven you to want this change in the first place.

By switching up your career path and transitioning out of the 9-5 environment you are literally thinking outside the box: the cubicle box, the office box, the corporate box.

Somewhere in there is a box, and you’re standing squarely outside it, looking back in and thinking something like, “I can’t stand it in there a second longer.”

Boxes, by their very nature, are stifling!

So the first thing to do to drum up a little momentum for your transition is to apply all your creativity and out-of-the-box-thinking to ensuring you aren’t accidentally trading one box for another.

Is the dream you have set upon genuinely following your passions, or have you curtailed it because your true dreams don’t feel like a viable career choice?

Because I’ve got news for you: everything is a potential career once you find the right way to look at it, and dedicate yourself to creating it!

Tip 2: Pinpoint Your Power

Everyone has a lot more power at their disposal than they realize. The block standing between you and seizing your power is probably really simple:

You’re not acknowledging it.

Often the things that make us most powerful are things we don’t consciously consider to be a form of power.

Power comes in many forms.

Intellectual power, creative power, bravery, tenacity, resilience…

There’s a deep well of untapped power and potential within you. All you have to do to unleash it is pinpoint exactly what form your unique brand of power takes.

When you do this, you will open your mind up to the transition before you, and find a way to lead yourself down the path that’s right for you.

Perhaps you’re exceptionally good at finding the heart of a problem quickly and really clearly defining it. Or maybe you’re a truly empathetic listener, able to put people at ease and ensure perfect efficiency.

Whatever your form of power is, don’t ignore it during this crucial transition. It will almost certainly play a big role in your new career, but it can be suuuuuper helpful in smoothing out the time before you fully step into your new role.

Uncover your gift and focus on it to help you improve upon and refine your vision for the path you're embarking on. Use it to fuel your motivation and keep that momentum going!

If you’re rooting around looking for your superpower and have no idea what it might be, try asking your family and friends. This is likely something that they are very aware of in you, and greatly appreciate about you, but have never actually verbalized because there was no real need.

People often assume we know our greatest strengths, because they seem too obvious when you’re viewing someone from the outside. It doesn’t occur to people we don’t know we’re amazing at a particular thing, because it seems so obvious to them!

Someone in your life will know what your unique brand of genius is, you just have to ask.

Tip 3: Thin-Slice

A common ‘tactic’ we use when we’re trying to deal with any transition is to wait to make changes. We feel we won’t be ready until we have accomplished a specific thing, got something we’re dreading out of the way, saved X amount of money, or otherwise done something fairly major.

It’s not unusual to fixate on a certain thing and believe its the one thing holding you back.

You can’t move forward until you’ve dealt with this huge, insurmountable obstacle.

For example, you’re lonely and desperate to find the love of your life, but rather than dating and putting yourself out there, you obsess over your diet.

You don’t feel you can find that special someone until you’ve lost X amount of weight.

Then you’ll be in ‘the perfect place’ for the transition into a life of love and happiness!

While you may be onto something in terms of your confidence increasing when you feel you are ‘ready’ for that big transition, the truth is that there is nothing stopping you from dating right now.

Career transitions are much the same. You’re embarking on a new relationship, with a new career and a new life, and you want to be at your best when you do it.

So you put it off, waiting until you’re ‘ready’.

This is really just a delay tactic you’re using to put off facing the upheaval that comes with the transition, and the various fears you have surrounding it.

If you feel like you’re not ‘ready’ to explore your passion and start making big steps towards that new career, start small.

Decide what matters to you and make space for a small part of it in your life.


Slice the tasks that you want to take on in the teeniest-tiny chunks you possibly can. Then take them one thin-slice at a time.

Bonus point if you commit to doing a thin-slice task EVERY day. Extra bonus points if you do it before 10am. That way regardless of anything else that might happen in a day, you’ll know that you’ve taken action to move you closer to your goals.

Be sure to take the Focus Formula Quiz so you can learn which activities you should be focusing on first.

Tip 4: Take The First BIG Step

The more you work your way through those small things you feel ready for, the more you will realize that you really are READY.

Ready to kick it up and take the first BIG step in your transition.

For me, that step was spending time on the side of my 9-5 job, training with a coach of my own, and learning everything I needed to know to become a coach in my own right.

That was a big, huge, scary step. When I first thought about coaching, it felt like I really wasn’t ready for it, that there were a million things I needed to do before I’d be able to start a coaching business.

But after spending time doing small things I was ready for, like researching, following coaches I admired, thinking about the type of work I’d like to do, and how I could help people, I realised that huge big step of committing to a coaching course wasn’t nearly as massive as it first seemed.

I wasn’t giving up my job as a lawyer. I wasn’t burning any bridges or walking away from my 9-5.

I was simply dipping my toe in the water and seeing what it felt like.

There was no pressure to actually do anything with my new coaching skills once I achieved them. I knew that, if I decided it wasn’t for me, I wouldn’t have lost anything but a little time and the money I’d invested in the course.

And that was fine.

That was comfortable. Because my momentum had built enough through small actions to accommodate a bigger one.

Tip 5: Release Resistance

The funny thing is, once you start that momentum going it snowballs. The next step in your journey always seems a little easier than the last, until suddenly you’re quite comfortable with the idea of doing something that, a few weeks or months previously, filled you with dread.

That being said, it doesn’t matter how far you go on your journey, there is always the potential to encounter resistance.

All creatives are bound to experience resistance at one time or another. The point is to create anyway. If you want more support overcoming creative resistance, then check out my posts Create More: Tips for Entrepreneurs and 8 Reminders for Entrepreneurs Feeling Stuck.

One part of the climb is a little harder than expected, and you find yourself lagging. You’re struggling to move yourself any further forward, either because you’re tired, or fed up, or simply because you really don’t want to face the bit that comes next.

It’s really helpful to remember that, even when you’re fully committed to the road and have been traveling down it for a while, it’s never too late to turn back.

If you find it’s not for you, nothing is keeping you from pausing, shifting direction, or turning around and going right back to where you were.

The amount you will have learned along the way will ensure that, even if you end up back at square one, it will be with a much deeper understanding of yourself, and the path that might eventually lead you to that happiness you crave.

Remembering this makes it a lot easier to accept that resistance when you encounter it along the way. You’ll still feel it, because it’s there and there’s no avoiding it; you’ll have to face it eventually. But rather than having this massive pressure to ‘do or die’...to deal with it or fail completely, you know there’s a safety net.

Persevering is considerably easier when you have that safety net.

So take a moment, feel the resistance, acknowledge what it is and what it means to you, and then release it.

The more you’re able to let go of the thoughts and feelings making you resist, the easier it will be to find the path of least resistance.

And Finally…

Remember, you’re not in this alone. Help and support are there if you need it, and you’re in charge of the pace you set during this transition. And you don’t need to figure everything out immediately. You’re better off getting focused and taking massive action.

Not sure what you should be focusing on?

Be sure to take the Focus Formula Quiz so you can get your customized formula to lead you to business success.