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The emotional journey of the self-employed.

Mapping the common emotional experience helps us to identify when and where we can collectively support the mental health of the self-employed.

Lots of my work within Leapers is about identifying the commonalities in the conversations with have within the community, and seeing how we can better support the issues which arise. If there's frequent conversation around late payments, we work gather resources to tackle the issue; if there's conversation about imposter syndrome, we capture the stories and make recommendations on how to get on top of it; if people aren't clear on what government support is available during COVID, we'll try and help signpost.

There are very specific issues and topics, and then there are more generalised themes which bounce around in my head as I try and think about how we can tackle the more system issues. Currently, I'm thinking a great deal about how Leapers can have more impact and be more sustainable. It's not realistic to think I can do this alone, so I need to build relationships with partners, with other organisations and communities, with government and society, to make more systemic and widespread change. We're not, nor do I think we'll ever be, a campaigning organisation, but if we can identify the key needs and moments where the best and most useful interventions for support can be made, and make them publicly available so that anyone and everyone can do their bit, then hopefully that moves us all collectively forward.

A drawing which I often scribble out for people is what I've referred to as the 'What I have I just done?' diagram. It's a sort of emotional rollercoaster which maps before, during and post the decision to move into self-employment, and helps me think about what type of content we should be creating and curating, and where the most effective interventions could be made. I'd promised myself to actually draw it out, so I can keep referring to it - this is that post.

Whilst I recognise that every single individual journey is very different, there do seem to be some very common patterns for many people - perhaps it's a bell curve, where it's true for a good majority, but there will always be plenty who experience things differently, and that's fine. I also recognise that this is based upon both lived experience, anecdote and a relatively small sample size of conversations, but I wanted to start somewhere, so we can build out from something, and improve upon it over time. I think this model mostly applies to people who work as individuals, and those who work on a project by project basis, so perhaps this is a journey for freelancers rather than those who are forced to be self-employed (such as gig-economy workers, those in industries where self-employment is defacto, such TV and Film, the trades and construction, or solo-retailers, so I'd love to know if your experience resonates with this regardless of category.

This is presented as an early draft of my thinking in this space - and the next step is to both validate it and identify the most places on the journey where we can better support people with what type of resources - as well as encouraging other organisations who are already present along this journey to help intervene and signpost too.

The Emotional Journey of the Self-Employed.


Pre-Leap Stage (-6 months)

Before the decision is made to leap into self-employment, there’s a whole load of mixed anxiety about how it will work, where you’ll get clients from, whether it’s the right thing to do, what other options might exist, when is the right time, can I afford it?

It’s a critical time to seek insight from others, whilst balancing your own gut instinct and rational information on how to proceed.

For some, it’s an enforced decision, perhaps they’re not able to find permanent work which suits their needs - so the wavy line might be more below the baseline.

For others, they might be really excited about starting self-employment, so the wavy line might be above the baseline, but they might also be struggling with their current employment or other circumstances.

Generally - this phase is very wavy.

Early Stage (0-3 months)

There’s quite often a ‘trigger’ moment where the decision is made to "let's do this" - it’s quite often the first client project, which gives people the confidence - and as that project often comes from your own personal network, you might know them and you’ve actively decided to do this work, it feels great - you’re on your own terms, it’s a paying project, you’re setting up your ways of working and doing some great work. A brilliant high.

Quite often though, that high is rapidly followed by a dramatic drop - as you finish your first project. Perhaps you didn’t start lining up the next piece of work. Perhaps you’ve realised you’ve not seen anyone else for three weeks whilst working, perhaps you hadn’t figured out what you need to put aside for tax or how to invoice or worse, there’s a debate over the scope of work or your first late payment.

It’s critical here to surround yourself with others who get it - but can feel hard to ‘admit’ that you don’t know what you’re doing, or that perhaps you have a feeling the decision you made might be wrong for you - so often people will ‘tough it out’.

There can also often be a sense of “what I have done?” as you recognise the gaps in your own support network and how the structure of your day might be boundaryless.

Generally - this phase is quite roller-coaster like, with high highs and scary lows.

Establishing Stage (3-12 months)

The next project comes in - you start finding your feet, you set up a few processes to integrate work into your life, and made started building a support structure - whether formally or informally. Things start to feel a little easier as you perhaps get into a rhythm of finding work, doing the work, and finding the next piece of work.

Of course, there’s a huge variance in each individual situation here, many people don’t have the ‘what have I done’ drop, so almost move through this phase blindly and fall into a way of working automatically on autopilot, driven by needs/demands rather than actively designing ways of working. Some people are just super busy and are just getting on with working. Others might be really struggling and trying to figure things out.

This is where there’s a critical inflection point - and reflection upon your own wellbeing is essential - so that you don’t continue to sit below the baseline, or wiggle above and below constantly.

Generally - this phase can feel upwardly positive as you establish your ways of working.


Your ways of working and habits are settling in now, for better or for worse.

You’ll probably be in one of four trajectories:

growing - you’ve established some great habits and support structures for your wellbeing, you feel positive and supported, are aware of the things that cause you stress, and developing plans to build resilience.

managing - you’re generally on top of things, of course you have your ups and downs, but it feels good, and you’re on average above your baseline. there’s always more you can do, and always new things which rock the boat - but you’ve got some decent habits and support in place. This feels good, normal, fine.

struggling - you’re doing okay, but it can often feel like a constant effort to keep your head above water, on top of your experience, and whilst there are enough highs to keep you doing this, the dips are tiring. Tiring is probably the key word - it feels like hard work most of the time, and if you don’t have the right support structure, it can feel really hard.

overwhelming - there’s more of a feeling of struggle than success, you’re not keeping on top of stress, and lots of your time goes on worrying about work, it affects your personal life significantly. you’re pushing on, really trying to make it work, but perhaps don’t have the support structure you need

Generally - this phase is very personal and reflective of the work you’ve invested in your own wellbeing at work.


Naturally - you can move between any of these states within the emerging phase over time.

Fortunately - the emerging and establishing phases are not linear - you can almost see them as a constant loop, and take a step into re-establishing healthy habits, stronger support networks and better working relationships - but it takes something for you to actively think about what state you’re currently in, and an active choice to do something about it.

Often there can be a trigger moment in emerging which makes you think “hold, on, this isn’t sustainable” - which makes you look for further support or investigate changes to how you work - these can be big moments like illness, losing a client, having a baby; which force a change, or they can come about through reflection and considering how you build a stronger way of working for the future.

So the final phase ‘sustaining’ is a perpetual state of reflecting upon how you’re doing, identifying where you can improve, building improved habits and support structures, and establishing positive ways of working.

At every stage, there’s likely to be proactive consideration and reactive response to influences on your wellbeing whilst self-employed - but proactive is always easier to manage, as you can plan and consider over time, rather than being forced to act.

Generally - the wavy line is a little less spiky and has an upward trajectory if you’ve built the right wellbeing plans for your own particular needs.