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It’s good to talk.

Who would you talk to about your decision making process when considering making a Leap?

Coffee and Conversation — a critical path to your Leap.

++ Your Partner

If you have a significant other in life, discussing your thoughts with your partner is undoubtedly essential — especially if you have shared responsibilities such as bills or family. In fact, anyone affected by your decision is a stakeholder — take their views on board, and see how your decisions have an impact beyond you. This might be the hardest conversation to have — and see it as an ongoing conversation, not a single chat. Working this out together is only going to make your journey better supported.

++ Your friends

This group of people know you well, really well. In fact, they’re probably the group who you are already sharing your thoughts with. Bear in mind though, friends can often be supportive of your ideas, hopes and dreams — regardless of how practical they may be.

++ Your ex-bosses

If you’re still on good terms with previous colleagues or bosses from other jobs, this is a great resource to reach out to. They knew you professionally, not just personally — they are potentially less emotionally engaged in your future plans, and can see your skills and gaps with some clarity, and can give you a view on the realities of the workplace right now — what challenges are they seeing, what opportunities are available; and who knows — it could even create a new opportunity for you in the future.

++ Mentors and Coaches

Seeking professional support for career advancement is always a route you can take. Whilst it can be costly, see it as an investment in your future salary or happiness, sort of like reverse insurance, pay a little bit now for greater rewards later. The biggest benefit of having a more formal coaching or mentoring relationship is that you’ll be able to work forward on your journey together — and benefit from the wealth of experience from the coach.

++ Your Current Boss

This might seem like an odd conversation to have, but your current boss has a responsibility to develop you and your career forward. Not every leap is about leaving a company, or even a role. Conversations with your current organisation about how the leap can happen within your current role or business are often fruitful — and commonly, it seems to be those who ask are more likely to get, compared to those who simply don’t push a conversation about development. Even if you’re not comfortable talking about your next role, or are committed to moving on — a conversation with your manager can help you identify your strengths and weaknesses, in order to develop a plan for your own development.

++ Expert Patients

The phrase ‘expert patient’ is stolen from healthcare, where patients are connected with other patients who have already been through treatment. This gives the inbound patient the opportunity to talk with someone who isn’t a Doctor, but knows what the process is really like. They have no reason to lie or emotional tie to you — they just call it how it is. Find an expert patient for your career, someone who has been there before, someone who has already done it, and get the low-down, warts and all. There’s no shortage of expert patients on the Leapers community itself, just ask a question, and see if you can find someone with experience of what you’re going through — that’s the whole point of the project.

++ Potential Future Bosses

This is both shrewd and valuable, have a conversation with people you look up to, that you might want to work with in the future, that you think may be included in your journey — find out what they think, what they’re looking for, ask for advice and guidance and build a relationship with people who perhaps might be your manager in the future.

++ Complete Strangers

Whilst it can seem extremely odd having a conversation with someone you don’t know, talking to someone completely outside of your circle, industry and network can be hugely valuable. Not only will there be observations which have parallels to your journey, there will also be things you discover which you’d not ever considered, helping to better inform your thinking process. Personally, its been these conversations which have been the most fruitful for me, shaping and reforming my view on what I could be doing next. The dreaded ‘Filter Bubble’ doesn’t just apply to news and current affairs, but also our own biases on how we see the future, and breaking out of that bubble, connecting with people who are fresh and have new perspectives can help your process be so much richer.

++ Yourself

Finally, and perhaps most importantly, you need to have some serious conversations with yourself. Capture the thoughts, observations, questions, concerns which flow through your head and keep track of them — use a notebook, a word file, emails to yourself — whatever technique works, but don’t lose the questions and concerns you find bubbling up. Use them to guide your conversations with others, and aim to try and answer those which you feel are holding you back the most.



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Matthew Knight

Chief Freelance Officer. Strategist. Supporting the mental health of the self-employed. Building teams which work better.