‘Should-ing’ all over yourself? How to get what you really want!

Sep 16, 2021

I work with high-achieving entrepreneurs and professionals who are successful in their careers. From the outside, their lives look picture perfect. On the inside, they’re often deeply unhappy.

Why? Because they’ve been conditioned to follow a traditional career path or settle for a sensible job. One that gives them wealth, success and the security of a steady pay cheque.

They contact me because they want help to clarify their career direction or start a business. But in reality, they have no idea who they are or what they really want.

And, I get it. I’ve been there too.

In my corporate job, I drove myself to reach the next sales target, financial result or promotion, was constantly stressed and exhausted. I’d look at the successful people around me and followed their example.

Then, I started my business because I wanted more freedom and balance — yet 5 years later, I had none. I lacked a clear purpose behind what I was doing — beyond overachievement, making money and external success.

This is because I was starting from the outside in — striving to reach someone else’s version of success. As result, I spent the better part of my career working towards what I thought I ‘should’ be doing.

These are classic examples of what I call ‘should-ing’ all over yourself. Ignoring what you want, in favour of what you think you ‘should’ do. Or put pressure on yourself to ‘be’ a certain way, rather than ‘who’ you truly are.

As a result, you struggle to make aligned decisions, beneficial changes or create the results you desire. You feel guilty for not staying true to what you want. Over time, as the cycle continues, you end up overwhelmed, unhappy or unfulfilled.

Are you should-ing all over yourself?

Read on to learn 6 practical steps to break this habit — once and for all! You’ll find out how to stop the ‘shoulds’ to reconnect with who you authentically are and what you actually want.


The first step is awareness. By observing your language and acknowledging when you use the word ‘should’.

‘Should’ is a judgement you picked up somewhere in the past and adopted as your own. It’s the voice of your parents, society, your conditioning or life experience. A form of self-sabotage — a fear or limiting belief holding you back from what you want.

This voice feels like it’s your own because it’s so deeply ingrained in your subconscious. However, it doesn’t belong to you. The ‘should’ — and negative thoughts and feelings that accompany it — are separate to you, not part of you.

Notice when you say it. Without this awareness, you’ll end up shoulding all over yourself without even realising it!


When you notice the ‘should’, pause and question it. Does this voice belong to you — or someone else? More often than not, it’s the voice of self-sabotage.

Identify the belief behind the ‘should’. What does this voice say? For example, you ‘should’ forget about what you want because it’s not possible, achievable, realistic — or even an option!

Finally, challenge it — who says so?! Remember, this voice doesn’t belong to you. Therefore, it’s within your complete control how you choose to respond to it.


Pay attention to your behaviour. When you take action, are you doing it because you want to or you feel you should?

If your answer is ‘should’, ask yourself — what’s the fear? What are you afraid will happen if you don’t do it?

Even if your actions don’t change, the fact you even questioned your behaviour will get you to start thinking about what you do want.


Once you notice the ‘should’ and question it, consciously choose what you want to do with it. Answer truthfully — do I actually want to do this? Listen carefully for the YES or NO!

If you have two conflicting ‘shoulds’ — prioritise! A simple example is: ‘I ‘should’ work hard and do extra hours to build my business/get the promotion.’ Versus: ‘I ‘should’ get home on time so I can spend time with my child and be a good parent.’

In these situations, ask yourself: What is more important? Right now, in this moment?

Remember you have a choice. The power to choose what you really want!


Next, get clear on exactly what you do want. Knowing your vision and purpose will help you stay connected to what is right for you, rather than what others think you ‘should’ do.

This is about defining your own version of success. After years of chasing external success, I finally figured out this needs to begin from the inside out. Because unless I knew who I was and what I wanted, I was never going to thrive!

To stay on track with this, reverse engineer your vision into specific, measurable goals. Then identify the action steps you need to complete to reach them. If you know what you want — your vision — your next steps will be clear.

Put aside time to focus on what you do want. Keep taking action towards your goals, even if it’s for 15 minutes each day. Focus on the next best step, one at a time.


The final stage is to permanently remove the ‘shoulds’ from your vocabulary. Along with its close family members — ‘must’, ‘have to’ and ‘can’t’. The more you can disengage from the words that limit you, the easier it is to stay connected to what you want.

Whenever you notice yourself saying ‘I should’, focus instead on ‘I want’. Take charge and start going after what you do want.

Commit to changing ‘I can’t’ to ‘I won’t’. This is about the power of choice and owning your decisions. Ask yourself what you really want — and stop shoulding all over yourself!

This process has helped my clients and I stand firmly in who we are and stop giving up what we want in favour of what we feel we’re supposed to do. I hope these steps support you too!

Ready to quit the ‘should’s’ and start taking steps to create the career you want?

Let’s chat! Book your free 30 minute consult HERE to get started.

Stacey Back is a Career Strategist, Leadership Coach + Founder of Profile Careers. She helps high-achievers at a career crossroads find the work that lights them up, increase their income, impact and create a career + life on their terms. Stacey works virtually with individuals and organisations based across the globe.