Nobody tells you about what the first 12 months of building a portfolio career are really like.

They tell you about the leap, the courage, and all that glorious freedom. There will be a sunrise laptop photo with a caption about finally doing it on your own terms…I may have been guilty of this one, sorry about that.

They don’t tell you about the Tuesday afternoon when your calendar is empty, your inbox has three emails in it, and you’re standing in your kitchen on your third cottage cheese bagel (gotta get the protein in), wondering if you’ve made a catastrophic mistake.

I want to talk about that Tuesday afternoon. And all the other ones like it.

Because if you’re in your first year of building a portfolio career, you are almost certainly experiencing some version of what I’m about to describe. And you’re almost certainly wondering: is this normal?

Yes, it is. Here’s the field report aggregated from hundreds of women I’ve mentored.

Subscribe now

1. You will think about going back to full-time work. Daily.Not because you want to, but your nervous system wants the thing it knows. A salary that lands on the same date every month. A calendar someone else fills. A structure that tells you where to be and what matters.

This is withdrawal and not a sign you made the wrong decision. You spent ten, fifteen, or twenty years inside a system that gave you external scaffolding for your identity, your schedule and your sense of progress. That scaffolding is gone now.

Your brain is looking for the familiar because the unfamiliar feels like danger (cue mental images of you not being able to buy food because you left a stable job).

I promise, it passes, but it does take longer than you think, and on bad days, sometimes it comes back.

2. You will fall in love with working alone. Then you will miss having colleagues, and it will confuse you.

The first few months feel like a holiday. No politics, no pointless meetings, no performing. Just you and the work.

Then one morning you’ll realise you haven’t spoken to another adult about anything work-related in days. And you’ll miss the people. Not the org chart or the reporting lines, but the shorthand you had with someone. The debrief after a hard call. The person who just got it without you having to explain.

Make sure you carve out time to build a network of portfolio career colleagues who act as teammates. They become your support system.

3. You will miss the toxic relationship you had with your inbox.

Hundreds of emails, Teams notifications, Slack pings, back-to-back meetings from 8am to 6pm. You hated it. You complained about it constantly.

And now you miss it. Because all of that noise made you feel like you were doing something. Proof of relevance and that you were needed.

Be honest about what you’re actually grieving. It’s not the emails. It’s the feeling of being in demand.

4. You will say “I hate selling” at least a hundred times a week.

Then you will slowly, painfully realise that in year one, your primary job title is Head of Sales. Not strategist, consultant, or advisor. Head of Sales.

Nothing else moves until someone pays you.

The women who stall in year one are almost never the ones without skills. They’re the ones who built everything except a sales pipeline.

They have a beautiful website, a polished offer, a Canva template for their Instagram, and zero conversations with people who could actually hire them (I feel a little exposed and hurt by my own words here).

Selling isn’t a phase you push through. It is the infrastructure of a portfolio career.

The sooner you make peace with that, the sooner everything else starts working.

Leave a comment

5. You will say yes to work you should say no to, at a price you should never have quoted.Your brain is telling you that you’re starting from scratch. That you should be grateful that anyone wants to hire you, and you need to “get runs on the board” before you can charge properly.

This is your friendly reminder that you are not starting from scratch. You have years of experience! You solved problems last month that most people can’t solve at all. But something about leaving corporate made you forget all of it.

This is the translation problem I talk about constantly. Your expertise didn’t disappear. Your ability to articulate it, price it, and sell it without a company name behind you is the muscle you haven’t built yet.

It’s a skills gap, not a confidence issue.

It’s fixable and learnable.

You can do this.

6. You will have no idea if you’re doing a good job.

This one creeps up slowly. In corporate, you had performance reviews, KPIs, and a manager who told you where you stood. You probably complained about the feedback process. Called it broken and resented the arbitrary ratings.

Now there’s nothing. No one is telling you whether the work you did last week was excellent or average. Just you and the silence of your own standards, which you haven’t figured out how to set yet.

That feedback loop you resented was also the only thing confirming you were on track. Without it, every quiet week feels like evidence you’re failing.

The faster you build your own definition of “success” for this new life, the faster you stop borrowing corporate’s.

7. You will recreate the exact working pattern that burnt you out.

Back-to-back calls, saying yes to everything, working evenings. When the calls dry up, you’ll fill the gaps with admin, research, and “strategy sessions” that are really just moving Post-it notes around. You’ll reorganise your Google Drive, attend three free webinars, and read another book about building a business instead of actually building one.

You left corporate to stop doing this. And within three months, you’ve rebuilt it.

Different context, same rhythm.

You can change what you do without changing how you do it (read that again). If you don’t address the operating system underneath, the pattern follows you. It doesn’t care whether you’re employed or independent.

It cares about what you believe “working hard” looks like.

The hardest skill in your first year isn’t selling or pricing or visibility.

It’s learning to sit with space and not fill it.

8. You will agonise over “visibility” without knowing what it actually means.

You’ll hear that you need to “be visible.” You’ll interpret this as “post on TikTok every day” or “build a personal brand” and immediately feel sick. So you’ll either avoid it entirely or throw yourself into content creation that feels performative and goes nowhere.

Visibility is findability. Can the people who need what you do, find you? That might mean LinkedIn. It might mean ten targeted emails. It might mean showing up in one room consistently for six months. It almost certainly does not mean dancing on Reels.

No judgment if that’s your vibe.

Subscribe now

9. You will tell someone what you do at a dinner party and watch their face do the thing.

The polite nod followed by a slight tilt. The “oh, that sounds... interesting.” And you’ll realise you still can’t describe what you do in one sentence that makes sense to someone outside your head.

“I’m the CFO at [insert company]” used to do all the work for you. A few words and everyone understood your value, your status and your place in the room. Now you’re starting from something new, and the sentence isn’t there yet.

The instinct is to list everything (stop that).

You don’t have to squeeze your entire portfolio into one sentence. A dinner party doesn’t need your full offering. It needs one line that makes someone lean in and ask a follow-up question.

Stop listing your activities. Name a problem you solve. Pick the most relevant one for the room you’re in.

10. You will discover your network can’t help you. Not because they don’t want to, but because they can’t.

Your corporate network is full of people who think you’re brilliant. They’ll champion you, recommend you to everyone at the school gate, tell the world about your new thing.

But they can’t hire you.

They’re what I call Players, not Payers. Players are your cheerleaders, but they can't pay your bills. You don't need more connections. You need more people who can write a cheque.

11. You will build something nobody asked for because it felt safe.

A course, a framework, a twelve-week programme with a workbook and a Canva sales page. You spent three months on it. Nobody bought it.

Meanwhile, someone asked you to help them with something straightforward last Tuesday, and you almost said no because it felt “too simple” to charge for.

The things people will pay you for in year one are rarely the things you want to be known for in year five. Start where the demand already is.

12. You will oscillate between “I’m a genius” and “I’ve ruined my life.” Sometimes in the same morning.

At 9am, you’ll land a new client and feel invincible. By 11am, you’ll check your bank account and spiral. By 2pm, you’ll have a great conversation that reminds you why you’re doing this. By 4pm, you’ll be on LinkedIn, looking at jobs you’d never actually take.

You are building a new identity while trying to earn a living from it. Both things are happening at once. The emotional whiplash is part of the process, not a sign that you are broken.

13. You will expect to replace your corporate salary immediately. And then feel like a failure when you don’t.

You’ll constantly compare what you earned this month with what you used to earn in your corporate job. And then you will cry into a bag of crisps when your current income is lower.

But a portfolio career doesn’t work like a salary. It works like a financial portfolio. You don’t invest everything into one stock on day one and expect full returns by Friday. You build across multiple positions over time.

Some are stable and defensive.

Some are growth plays.

Some take years to mature.

Your first year's income will probably come from one or two core income streams.

That’s your defensive position. The leveraged income, the digital products, the paid newsletter, and the speaking are growth plays that compound later.

Stop measuring year one against your year fifteen corporate salary.

You haven’t failed! You’ve started building a portfolio that isn’t mature yet.

If you’re somewhere in this list right now, here’s the final thing I will say…

None of this means you chose wrong. It just means you’re in it, and “in it” looks nothing like the highlight reel you’ve seen on social media.

And if you are asking yourself, “Is this normal?”

Yes. This is exactly what it looks like.

Want to chat?I’ll be answering Q&As on all things portfolio career strategy, future of work trends & why I believe the CV is dead (and what’s coming next). If you have a question you’d like to ask a question, why not join the chat - it’s free.

Did you enjoy this?If this landed, share it with someone who’s sitting on raw materials and doesn’t know what to do with it yet.

Share

Nobody tells you about what the first 12 months of building a portfolio career are really like.

They tell you about the leap, the courage, and all that glorious freedom. There will be a sunrise laptop photo with a caption about finally doing it on your own terms…I may have been guilty of this one, sorry about that.

They don’t tell you about the Tuesday afternoon when your calendar is empty, your inbox has three emails in it, and you’re standing in your kitchen on your third cottage cheese bagel (gotta get the protein in), wondering if you’ve made a catastrophic mistake.

I want to talk about that Tuesday afternoon. And all the other ones like it.

Because if you’re in your first year of building a portfolio career, you are almost certainly experiencing some version of what I’m about to describe. And you’re almost certainly wondering: is this normal?

Yes, it is. Here’s the field report aggregated from hundreds of women I’ve mentored.

Subscribe now

1. You will think about going back to full-time work. Daily.

Not because you want to, but your nervous system wants the thing it knows. A salary that lands on the same date every month. A calendar someone else fills. A structure that tells you where to be and what matters.

This is withdrawal and not a sign you made the wrong decision. You spent ten, fifteen, or twenty years inside a system that gave you external scaffolding for your identity, your schedule and your sense of progress. That scaffolding is gone now.

Your brain is looking for the familiar because the unfamiliar feels like danger (cue mental images of you not being able to buy food because you left a stable job).

I promise, it passes, but it does take longer than you think, and on bad days, sometimes it comes back.

2. You will fall in love with working alone. Then you will miss having colleagues, and it will confuse you.

The first few months feel like a holiday. No politics, no pointless meetings, no performing. Just you and the work.

Then one morning you’ll realise you haven’t spoken to another adult about anything work-related in days. And you’ll miss the people. Not the org chart or the reporting lines, but the shorthand you had with someone. The debrief after a hard call. The person who just got it without you having to explain.

Make sure you carve out time to build a network of portfolio career colleagues who act as teammates. They become your support system.

3. You will miss the toxic relationship you had with your inbox.

Hundreds of emails, Teams notifications, Slack pings, back-to-back meetings from 8am to 6pm. You hated it. You complained about it constantly.

And now you miss it. Because all of that noise made you feel like you were doing something. Proof of relevance and that you were needed.

Be honest about what you’re actually grieving. It’s not the emails. It’s the feeling of being in demand.

4. You will say “I hate selling” at least a hundred times a week.

Then you will slowly, painfully realise that in year one, your primary job title is Head of Sales. Not strategist, consultant, or advisor. Head of Sales.

Nothing else moves until someone pays you.

The women who stall in year one are almost never the ones without skills. They’re the ones who built everything except a sales pipeline.

They have a beautiful website, a polished offer, a Canva template for their Instagram, and zero conversations with people who could actually hire them (I feel a little exposed and hurt by my own words here).

Selling isn’t a phase you push through. It is the infrastructure of a portfolio career.

The sooner you make peace with that, the sooner everything else starts working.

Leave a comment

5. You will say yes to work you should say no to, at a price you should never have quoted.

Your brain is telling you that you’re starting from scratch. That you should be grateful that anyone wants to hire you, and you need to “get runs on the board” before you can charge properly.

This is your friendly reminder that you are not starting from scratch. You have years of experience! You solved problems last month that most people can’t solve at all. But something about leaving corporate made you forget all of it.

This is the translation problem I talk about constantly. Your expertise didn’t disappear. Your ability to articulate it, price it, and sell it without a company name behind you is the muscle you haven’t built yet.

It’s a skills gap, not a confidence issue.

It’s fixable and learnable.

You can do this.

6. You will have no idea if you’re doing a good job.

This one creeps up slowly. In corporate, you had performance reviews, KPIs, and a manager who told you where you stood. You probably complained about the feedback process. Called it broken and resented the arbitrary ratings.

Now there’s nothing. No one is telling you whether the work you did last week was excellent or average. Just you and the silence of your own standards, which you haven’t figured out how to set yet.

That feedback loop you resented was also the only thing confirming you were on track. Without it, every quiet week feels like evidence you’re failing.

The faster you build your own definition of “success” for this new life, the faster you stop borrowing corporate’s.

7. You will recreate the exact working pattern that burnt you out.

Back-to-back calls, saying yes to everything, working evenings. When the calls dry up, you’ll fill the gaps with admin, research, and “strategy sessions” that are really just moving Post-it notes around. You’ll reorganise your Google Drive, attend three free webinars, and read another book about building a business instead of actually building one.

You left corporate to stop doing this. And within three months, you’ve rebuilt it.

Different context, same rhythm.

You can change what you do without changing how you do it (read that again). If you don’t address the operating system underneath, the pattern follows you. It doesn’t care whether you’re employed or independent.

It cares about what you believe “working hard” looks like.

The hardest skill in your first year isn’t selling or pricing or visibility.

It’s learning to sit with space and not fill it.

8. You will agonise over “visibility” without knowing what it actually means.

You’ll hear that you need to “be visible.” You’ll interpret this as “post on TikTok every day” or “build a personal brand” and immediately feel sick. So you’ll either avoid it entirely or throw yourself into content creation that feels performative and goes nowhere.

Visibility is findability. Can the people who need what you do, find you? That might mean LinkedIn. It might mean ten targeted emails. It might mean showing up in one room consistently for six months. It almost certainly does not mean dancing on Reels.

No judgment if that’s your vibe.

Subscribe now

9. You will tell someone what you do at a dinner party and watch their face do the thing.

The polite nod followed by a slight tilt. The “oh, that sounds... interesting.” And you’ll realise you still can’t describe what you do in one sentence that makes sense to someone outside your head.

“I’m the CFO at [insert company]” used to do all the work for you. A few words and everyone understood your value, your status and your place in the room. Now you’re starting from something new, and the sentence isn’t there yet.

The instinct is to list everything (stop that).

You don’t have to squeeze your entire portfolio into one sentence. A dinner party doesn’t need your full offering. It needs one line that makes someone lean in and ask a follow-up question.

Stop listing your activities. Name a problem you solve. Pick the most relevant one for the room you’re in.

10. You will discover your network can’t help you. Not because they don’t want to, but because they can’t.

Your corporate network is full of people who think you’re brilliant. They’ll champion you, recommend you to everyone at the school gate, tell the world about your new thing.

But they can’t hire you.

They’re what I call Players, not Payers. Players are your cheerleaders, but they can't pay your bills. You don't need more connections. You need more people who can write a cheque.

11. You will build something nobody asked for because it felt safe.

A course, a framework, a twelve-week programme with a workbook and a Canva sales page. You spent three months on it. Nobody bought it.

Meanwhile, someone asked you to help them with something straightforward last Tuesday, and you almost said no because it felt “too simple” to charge for.

The things people will pay you for in year one are rarely the things you want to be known for in year five. Start where the demand already is.

12. You will oscillate between “I’m a genius” and “I’ve ruined my life.” Sometimes in the same morning.

At 9am, you’ll land a new client and feel invincible. By 11am, you’ll check your bank account and spiral. By 2pm, you’ll have a great conversation that reminds you why you’re doing this. By 4pm, you’ll be on LinkedIn, looking at jobs you’d never actually take.

You are building a new identity while trying to earn a living from it. Both things are happening at once. The emotional whiplash is part of the process, not a sign that you are broken.

13. You will expect to replace your corporate salary immediately. And then feel like a failure when you don’t.

You’ll constantly compare what you earned this month with what you used to earn in your corporate job. And then you will cry into a bag of crisps when your current income is lower.

But a portfolio career doesn’t work like a salary. It works like a financial portfolio. You don’t invest everything into one stock on day one and expect full returns by Friday. You build across multiple positions over time.

Some are stable and defensive.

Some are growth plays.

Some take years to mature.

Your first year's income will probably come from one or two core income streams.

That’s your defensive position. The leveraged income, the digital products, the paid newsletter, and the speaking are growth plays that compound later.

Stop measuring year one against your year fifteen corporate salary.

You haven’t failed! You’ve started building a portfolio that isn’t mature yet.

If you’re somewhere in this list right now, here’s the final thing I will say…

None of this means you chose wrong. It just means you’re in it, and “in it” looks nothing like the highlight reel you’ve seen on social media.

And if you are asking yourself, “Is this normal?”

Yes. This is exactly what it looks like.

Want to chat?

I’ll be answering Q&As on all things portfolio career strategy, future of work trends & why I believe the CV is dead (and what’s coming next). If you have a question you’d like to ask a question, why not join the chat - it’s free.

Did you enjoy this?

If this landed, share it with someone who’s sitting on raw materials and doesn’t know what to do with it yet.

Share