This week, let’s do a really uncomfortable exercise together.

A full reality check.

Forget your job title for a moment.

Instead, write down what your job actually involves.

Not what you think it should involve.

What you really do.

Think about a typical week.

The hours you work.

The client meetings.

The selling.

The delivery.

The team questions.

The approvals.

The emails.

The problems that find their way to you.

The decisions that apparently can’t be made without you.

The things you check because you’re not entirely confident they’ll happen otherwise.

The things you’ve been doing for so long that nobody has ever really questioned why you still do them.

Write all of it down.

Then add the salary.

The holidays.

The working hours.

The expectations.

How contactable you’re expected to be outside those hours.

How easily you can switch off.

How often somebody interrupts you.

How long you could realistically disappear before something needed your attention.

Now remove your name from the top.

Imagine somebody sent you that job description tomorrow.

And ask yourself: Would you apply for this job?

I did this exercise myself

I went through a version of this exercise myself a few years ago.

When I looked objectively at the job I’d created for myself inside Nuvem9, my conclusion was pretty straightforward.

I’d have been mad to take it.

Nobody had given me that job.

I’d built it. 

(My actual response involved considerably stronger language 😀)

Too many hours.

Too many different responsibilities.

Too many things dependent on me.

Too difficult to properly switch off.

And perhaps most frustratingly, too much of the work I actually enjoyed was being squeezed between everything else.

I’d created a role where I was simultaneously the business owner, CFO advisor, salesperson, relationship manager, people manager, reviewer, decision-maker and problem solver.

If there was a gap somewhere in the business, there was a reasonable chance I was filling it.

If somebody had advertised that role to me, I wouldn’t have applied.

Which led to a slightly uncomfortable realisation.

Nobody had given me that job.

I’d built it.

How did that happen?

I don’t think many founders deliberately design themselves a bad job.

It happens gradually.

At the beginning, you do everything because there’s nobody else to do it.

Then the business grows.

You hire people.

But a client says they still want to speak to you, so you keep that relationship.

You’re the strongest salesperson, so you continue selling.

You’re good at solving difficult problems, so the difficult problems keep finding you.

Someone isn’t quite ready to take responsibility for something, so you keep doing it for a little longer.

You’re closest to the numbers, so you make the decisions.

You’re quicker at doing something yourself than explaining it to somebody else.

Individually, almost every one of those decisions makes sense.

And then one day you realise that you’ve accumulated a job.

Your current role can simply be the result of hundreds of perfectly reasonable decisions that nobody ever subsequently revisited.

That’s certainly what had happened to me.

I didn’t want to leave the business

This was probably the most important part of the realisation.

I didn’t conclude that I wanted to sell Nuvem9.

I didn’t want to retire.

And I certainly didn’t want to stop working.

There were large parts of what I did that I really enjoyed.

I enjoyed working directly with business owners.

I enjoyed the strategic conversations.

I enjoyed understanding what was really happening inside a business and helping someone make a better decision because of it.

I enjoyed developing ideas.

I enjoyed building relationships.

The problem wasn’t Nuvem9.

And it wasn’t work.

I didn’t want to leave my business. I wanted to change my job inside it.

So I started doing that.

Not overnight.

And certainly not perfectly.

I became much more conscious about what genuinely required me and what simply involved me because it always had.

What could somebody else own?

What could be systemised?

What decisions could move elsewhere?

What knowledge needed to come out of my head?

What client relationships could become relationships with Nuvem9 rather than simply relationships with me?

What was I doing because it genuinely represented the best use of my time?

And what was I doing through habit?

Over time, the job changed.

Now I need to do the exercise again

That’s the interesting part.

Now the job I wanted a few years ago isn’t necessarily the job I want three years ahead.

I’ve recently been doing a lot of thinking about what I want my life and Nuvem9 to look like by the middle of 2029.

I’ve written over the last few weeks about wanting more options.

Fewer working hours.

More travel.

More time spent doing the work I genuinely enjoy.

A business less dependent upon me.

More revenue coming from things we’ve built and can use repeatedly.

So now there’s an obvious question sitting underneath all of that.

What do I actually want my job to be?

Not what I want Nuvem9 to look like.

What do I want my role inside Nuvem9 to look like?

I’m not trying to remove myself from Nuvem9.

I’m trying to become much more deliberate about where I remain within it.

Owner isn’t a job description

One of the problems with being a founder is that several completely different jobs get bundled together.

You can simultaneously be the:

1. Owner: The person whose capital is at risk and who ultimately receives the return
2. Leader: The person setting direction and making the biggest decisions
3. Manager: The person managing people, priorities and performance
4. Expert: The person doing the work the customer actually buys
5. Salesperson: The person creating the next piece of revenue
6. The Fixer: The person filling whatever gap remains

When one person performs all of those roles, it’s easy to stop seeing them as separate jobs.

So now imagine that they are.

Which ones would you actually apply for?

That’s a much more interesting question.

Perhaps you love selling. Perhaps you hate it.

Perhaps client delivery is the reason you started the business and you’d happily continue doing it forever. Perhaps it’s the first thing you’d stop tomorrow.

Perhaps you love leading people, but no longer want to be the technical expert.

Perhaps you want to remain the owner but have somebody else run the company.

Or perhaps you actually like most of your current job.

You just want to do less of it.

There’s no correct answer.

Freedom doesn’t mean doing nothing

I think this is where some of the conventional thinking about founder independence can become unhelpful.

There’s often an implied progression.

Start the business.

Build the team.

Become the CEO.

Remove yourself from delivery.

Appoint management.

Become the owner.

Exit.

However, why does that have to be the destination?

If you love working directly with clients, why would success require you to stop?

If you love selling, why automatically delegate it?

If you enjoy running the business five days a week, there’s nothing inherently superior about working three.

The objective isn’t to remove yourself for the sake of it.

Freedom doesn’t necessarily mean doing nothing.

It means being able to choose what you continue doing.

That’s the distinction I’m increasingly interested in.

Keep. Reduce. Remove.

So perhaps we can make our uncomfortable exercise slightly more useful.

Go back to that list of everything you currently do.

And put each activity into one of three categories.

Keep

What would you still actively choose to be doing three years from now?

Not tolerate.

Choose.

Reduce

What don’t you necessarily want to eliminate, but want to occupy far less of your time?

Remove

What should simply no longer require you?

This is essentially what I’m now doing again with my own role.

There are things I absolutely want to keep:

• High-level CFO advisory
• Strategic conversations with business owners
• Developing ideas and frameworks
• Writing and creating content
• Selected relationships and business development

Then there are other things I want to reduce:  

• Routine client accounting work
• Internal operational decision-making
• Reviewing work that should already be complete
• Being the automatic escalation point.

And, further, there are things I want to remove completely:

• Chasing
• Routine approvals
• Workflow management
• Administrative follow-up
• Owning tasks simply because historically I always have

The objective isn’t to disappear.

It’s to be much more deliberate about what remains.

Then add time

There’s another dimension to the exercise.

Saying: “I want to continue doing advisory work”

doesn’t really define a future job.

How much?

Five days a week?

Three?

How many clients?

How many meetings?

What decisions still require you?

How available are you when you’re supposedly not working?

Could you disappear for a month?

Could you travel for six weeks and work selectively?

Could you take Friday off without spending Friday checking whether everybody else is doing what they’re supposed to be doing?

A three-day working week where you’re still checking Slack, answering emails and resolving problems across seven days isn’t really a three-day working week.

So perhaps the future job description needs to answer:

What do I want to do?

How much of it do I want to do?

What decisions should still require me?

How available do I want to be when I’m not working?

Then comes the financial reality

Of course, there’s a danger here.

It’s very easy to design yourself a lovely future job.

Three days a week.

No people management.

No selling.

Only the clients you like.

Twelve weeks of holiday.

Excellent salary.

Unfortunately, the business gets a vote too.

Imagine you personally deliver £300k of a £1m company’s revenue.

You decide you no longer want to do delivery.

Fine.

However, that £300k doesn’t disappear from the economics because you’ve removed it from your job description.

Someone else has to deliver it.

Or different revenue has to replace it.

Or pricing has to change.

Or margins have to improve.

Or your income expectations have to change.

Or the business has to become smaller. 

The same applies to sales.

Last week I wrote about the Revenue Gap.

If your business needs to create another £600k of revenue next year and you’re still the person responsible for winning most of it, writing “minimal sales involvement” into your future job description doesn’t solve the problem.

You can redesign your job description, but the business still has to fund it.

Or put another way:

Delegating the work doesn’t delegate the economics.

That’s why I think this exercise matters beyond lifestyle.

Your desired job has to be compatible with the business you’re building.

Write the job you’d actually take

So perhaps it’s time to write a second job description.

Not the uncomfortable one describing what you do today.

The one dated three years from now.

What would make you genuinely want the job?

How many days would you work?

What would your primary responsibilities be?

What decisions would you still own?

How much client involvement would you have?

Would you sell?

Would you manage people?

What would you absolutely no longer do?

How long could you completely disconnect?

And importantly: What income does that job and the ownership of the business still need to provide you?

Then put the two job descriptions beside each other.

The job you have today.

The job you’d actually choose three years from now.

Look at the gap.

That gap tells you something incredibly useful.

If today you generate most of the sales but don’t want to in three years, the business needs another route to revenue.

If every major client relationship sits with you but you want to work three days, those relationships need to broaden.

If every difficult decision reaches you, the business needs more decision-making capability.

If most revenue depends upon your personal delivery, the revenue model needs to change.

If the business needs your constant presence, systems and accountability need to improve.

And if your desired lifestyle requires a certain level of income, the economics still need to support it.

The gap between the job you have and the job you want isn’t simply a lifestyle problem.

It’s a business design problem.

Would you apply?

A few years ago, when I looked at my own job and decided I’d have been mad to apply for it, the realisation helped me start changing it.

Now I’m doing the exercise again.

This time I’m not simply asking what I want to stop doing.

I’m asking a better question.

What do I still want to be doing three years from now?

I don’t think the goal is to build a business that doesn’t need you.

At least, that’s not my goal.

I want to build a business that doesn’t need me for anything I no longer choose to do.

And once you know what that future job looks like, there’s one final question.

How do you build the business that can actually support it?

Next week: Build Backwards From Freedom.