Growing ContentUK #3 - the mental challenges of bootstrapping

Today I’m going to chat about some of the mental challenges I’ve been feeling recently whilst growing ContentUK

Most of the time this bootstrapping journey is fun, inspiring and exciting. But sometimes it’s vulnerable, lonely and draining.

I’m sharing (oversharing?) some of the tougher bits I've been pondering lately; from how it seems impossible to have a proper break, the pressure for more income to feeling guilt and imposter syndrome.

These seem to be thoughts a lot of founders experience when I chat 1:1 with them but we don't always discuss these publicly.

The need for a break but feeling i can’t have one

I’m conscious that my mind needs a break beyond a couple of days. If i was employed, I’d book 2 weeks off work right now and stay off my laptop to fully recharge.

But it doesn’t really work like that when running your own business. Well, not with my current setup at least!

I have weekly commitments across running the community, sponsors, jobs to promote and no one to pass tasks onto. I don't (currently) have a system that would let things go on pause beyond a couple of days.

Whilst I might not be able to take a *full* 2-week break, I can have 2 weeks of doing the minimum required with a few hours of light work per day. Not quite the same as a full holiday but it's better than nothing!

It's okay to prioritise recharging and to let stuff drop.

The pressure to make more income with lockdown ending

ContentUK currently earns (almost) £800 MRR from members which gradually increases each month. I'm super proud of this. A mix of featured jobs, sponsors and writing gigs, tends to give me £1k revenue on top of that (all before taxes and expenses!).

Thanks to living with parents and the pandemic lifestyle, I’ve managed to live frugally on a low income. But as venues are opening up again, suddenly there’s pressure to get more income to have a comfortable life whilst memberships slowly grow. 

That’s on my mind. Either by ramping up ContentUK stuff or looking at other revenue streams. How do I boost ££ without losing sight of growing in a value-first way? How do I make the correct decisions for the community and my mental health without making the wrong ones due to money pressure?

Making space for socialising

The pandemic has made it easy to work on ContentUK without FOMO. I haven’t felt like I’ve missed out on much as everyone is in the same situation of ‘life is on hold’.

However, I’m conscious of wanting to make space for socialising soon without sacrificing the community and still growing the business.

A business is not worth it if you have to sacrifice your social life IMO. The whole point of self-employment (for me) is the freedom of how you use your time.

Does the current setup allow for this? How can I make sure it does?


I want to build a business that brings wealth, runs ethically and elevates people. Sometimes i feel I’m not doing enough.

I feel guilty and anxious easily.

I’ll spend hours ruminating about questions like:

‘Are members getting value or are they disappointed when they join?’

‘Is it okay to have some webinars for non-members or would that disappoint paying members?’

‘Have I upset this person?’

‘Am I supporting members enough?’

'Am I annoying?'

'Am I elevating people enough?'

It’s mostly illogical monkey-mind noise but these thoughts can interfere with cracking on with what's important and make me hold back for fear of putting a foot wrong.

No idea what I’m doing and imposter syndrome

I swing between feeling like a badass woman who KNOWS i’m going to make this a success eventually... to thinking:

‘I don’t have a CLUE what i’m doing or how this startup world operates'

'Other communities are 100x better than mine'

'If I’m no longer a content manager in my day job, can I still add value to content professionals?’

'When will they realise I'm a fraud?'

I try to accept these are normal thoughts and speak to someone or write them down when they appear to minimise the power. Not sure they'll ever fully disappear but getting them out does help. I'm getting better at reducing how long they hold power. When I spot these, I try to shut my laptop, walk my dog and reframe these into kinder thoughts.


Always feels a bit scary writing with vulnerability but it’s a comfort when I read other people’s honest experiences about entrepreneurship.

To reiterate, most of the time, I LOVE growing ContentUK but want to chat about the moments of doubt too, not just highs.

 Feel free to reach out if you can relate to anything I’ve spoken about :)

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