“If-then” planning: a self-leadership tool for navigating the unexpected.

I was recently in a mentoring session with one of my clients, a successful founder in the financial services sector, where we explored a simple tool, “if-then” planning.

She’s at a point in her business where she knows she wants to create more time and space, not just for rest, but to focus on the projects that feel urgent and important outside of her business. You know – that holy grail of business ownership! 

Her big-picture goal is to:

“To create the time and space to do the things that are calling me.”

But of course, the demands of business,  client responsibilities and default behaviours and thinking patterns don’’t always make it that easy. 

Not for my client. Not for any of us.

This is where if-then planning is really valuable – a small but powerful tool to turn good intentions into real, aligned action. One that’s especially valuable when you’re navigating adaptive challenges, shifting your business model, or simply trying to carve out more time for what matters most.

What is if-then planning?

You may have heard the saying “forewarned is forearmed”? I see If-then planning in this light.

It’s the act of pairing a specific situation (the “if”) with a pre-decided response (the “then”).

If [a specific trigger/event occurs], then [I will respond in this way].

It’s a way of preparing your future self to act in alignment with your values and goals, especially when pressure, distraction, or emotion (especially if you have a sparky, fast-brain driven by interest and novelty…)  might otherwise pull you off track.

The research behind this tool comes from behavioural psychology and the work of Dr Heidi Grant – she outlines a four-step approach to embedding habits through implementation intentions.

But this idea isn’t about habit-hacking.

It’s about self-leadership. About choosing your actions on purpose, so that your goals don’t remain ideas on a vision board – they become lived experience as you support yourself to turn ideas into action through self-knowledge. 

In the case of my client, she is an Enneagram 2 – The Helper, and this awareness helped us realise that introducing the If, then tool was forearming as beautiful 2’s can face these risks:

• Overcommitment & boundary issues
  Risk: Saying “yes” to too many commitments (business, community, personal) at the cost of your well-being.

• Seeking validation through “being needed”
  Risk: Deriving self-worth from being indispensable makes it harder to delegate or step back.

• Suppressing needs leading to resentment and burnout
  Risk: Prioritising what others want at the expense of your own desires

• Cognitive distortions: all-or-nothing & guilt loops
  Risk: Thought patterns that keep you stuck in cycles of overwork, guilt, or self-criticism.

• The “Martyr syndrome” → overextending to the point of exhaustion
  Risk: Taking pride in sacrificing yourself can lead to exhaustion and resentment.

Any and all of these behaviours will sabotage even the best of intentions to create more space and time for yourself! 

Five steps to put if-then planning into practice

Let’s walk through the approach I used with my client – and how you can apply it in your own life or business.

1. Clarify your big goal

I don’t encourage you to start by using the approach to help you tick any “should” boxes or KPIS you’re chasing. It is great for those (and just as good for “If my other half says this, THEN I’ll….moments 😆), but let’s go deeper for now. Perhaps try focusing on reconnecting to your “why.” What’s pulling you forward right now? What is most important to you at this stage of your business and life?

Example: “I want to create spaciousness in my schedule for deep work, rest, and long-term strategy.”

2. Break that goal down into subgoals

Big goals need structure to become actionable. Break yours into key areas of focus or outcomes.

Examples:

• Reduce client-facing time from 10 days to 6 per fortnight

• Delegate operations to a 2IC

• Take two 4–6 week totally unplugged breaks per year

3. Identify potential or common obstacles

Time to get honest… What usually derails you? What thoughts, habits, or external pressures tend to pull you off course?

Examples:

• I feel guilty stepping away, and so… I don’t! 

• I check email during my planning time

• I jump in to solve team issues before they ask for help

4. Create your if-then statements

This is where the shift happens. Create intentional “scripts” that support you to act differently next time those triggers arise.

Examples:

• IF I feel tempted to jump into a task I’ve delegated, THEN I’ll reconnect with my big goal and remember why stepping back matters.

• IF I get pulled toward admin during my strategic block, THEN I’ll put my phone on silent and set a 25-minute focus timer.

• IF a team member asks for input I know they can handle, THEN I’ll ask: “What would you do here?” instead of answering straight away.

• IF I’m asked to get involved in another volunteer role, THEN I’ll say “Thanks for asking – I’ll get back to you once I’ve checked my schedule”.

Yes, these might seem simple. .But don’t underestimate them – there’s power in simplicity! .

5. Rehearse and refine

Just like any practice, you’ll get better at If-then planning over time..So, keep your statements visible. Say them aloud. Track what works and update as needed. Congratulate yourself when you use them…

And if you’re a sparky-brained or fast-brained thinker like me, this is an approach that can be particularly helpful.

For those of us who live with ADHD or similar traits, it’s easy to drift, to follow shiny distractions, or to freeze under pressure. If-then planning offers structure without rigidity. I think of it as cognitive insurance or self-support breadcrumbs that lead me back onto the path I chose before someone or something tried to lead me astray…

This tool is also strategic self-compassion

It’s easier to follow through on what you already know most matters when you have a plan.

It’s self-leadership in action: creating the conditions where your best choices are more likely to happen. Not just when you’re energised and focused, but on the days when you’re tired, distracted, or disheartened too.

Because that’s when you most need extra support tools. In advance.

Will you give this idea a go? I’d love to hear how it works for you.

Angela

P.S: Do you know your Enneagram?

I mentioned that the client this post was inspired by is an Enneagram 2 – The Helper – and how that insight guided the way we approached her if-then planning.

I love the Enneagram! It’s a personal development tool that explores nine core personality types, and each has distinct patterns of thinking, feeling, and behaving. Think of it as a lens rather than a label – it’s one of many tools that help us understand ourselves better. It delves into the reasons behind the things we do… a handy self-leadership tool. 

I bring the Enneagram into my mentoring and retreats because it can help highlight patterns that may be unconsciously guiding your decisions, in ways that are supportive or in ways that are classically self-sabotaging.

I’m a classic 7 – the Enthusiast, and some of the risks I need to plan for with my own If, THEN scripts include;

• Scattered focus and shiny object syndrome

• Avoiding discomfort and difficult emotions

• Fear of missing out

• Avoiding closure and reflection

If you’re curious about your own Enneagram type, I’d love to explore it with you as part of my business, life, and ADHD-specific mentoring and coaching programs. You can book a chat with me here.  

Angela Raspass