But as I write I am half way through my husband being away for a week and I am hanging by a thread. I don’t like the term solo parenting, my parents were divorced and I spent most of the week with my single mum so it gives me the ick.

BUT, wowsers, I’m tired. The boys miss their dad.

Upsource has had our busiest month on record.🍾 But like all wins, it has its downsides (Hello big VAT bill and my closest shave with clashflow worry to date.)

The growth is coming and the pressures have felt real.

But I guess this is all very timely for this newsletter on awards. Why, you ask?

I’ll be honest, the Upsource team has had some fantastic award wins over the past few years, but there is always something behind the scenes soon after that reminds you why those wins are important.

Because the day-to-day as a business owner, as a VA supporting others really can be a challenge. You need to celebrate yourself.

To tie in with Oscar season (and the launch of the UK VA awards obvs) I’m giving you my lowdown on why you should be nominating yourself for awards in 2026. Most of my points apply to any industry, not just ours, so please, share this and encourage your friends outside the industry to apply for their own awards too!

If you’re looking for some practical tips on how to craft a winning award entry - stay tuned, the Substack is having a glow up in March✨and we’ll have awards advice and much more coming your way.

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Points of Business: Why you should nominate yourself for an award in 2026

You’ve got to look back to go forward

Be honest now, how often do you make that time to reflect on how far you’ve come? Any good award entry will put you through that process.

I wasn’t going to enter the UK VA awards in 2025. Last minute I said, “I might as well!”

So why did I apply? I was in no man’s land waiting to hear back on my application for the GC 10KSB programme and wanted to take my mind off it. I didn’t really think Upsource had “achieved” enough as a business to win.

It turns out, we had achieved A LOT. I just hadn’t appreciated it.

AAAAAAnnd we’d achieved “enough” to win Lead VA with a Large Team and for Bump to Business Owner to nab team of the year.

So if you feel that the past year has been a little lacklustre, give it a go- actually write down what you’ve done in the last 12 months, guaranteed it’s more than you think.

It shows commitment

Bear with me here. I think entering an award demonstrates commitment to your business, industry, belief, passion, purpose.

Whatever that means for you.

If you are committed, that will always be recognised. It just might take time.

Entered and didn’t win? Come back and try again.

Never expect to do anything well the first time. Most times I fail. But if I’m committed, the failure is worth it.

I get it, “that’s fine for someone who won UK Best Newcomer VA 2021 within a year of business”.🤨

But, 2022, 2023?

I entered loads of awards and didn’t win. That’s ok, it wasn’t my time and I knew it.

If it’s meant to be, it will happen and you will get recognised: stick with it.

The application pushes you out your comfort zone

Often awards ask you for things you need to go get. Or have an unwritten rule they expect publicity from you. Whether it’s:

• Getting those client testimonials you have been too scared to ask for

• Really analysing your finances and where you’d like to be

• Putting your goals to paper and sharing them

• Or posting on socials you are up for an award

Do it.

It is only a good thing to challenge yourself.

You’ll make friends

Cheesy but true.

I’m gonna steal a post from a colleague here

I hard relate to this.

I dragged my husband along to my first Miss Jones Group Awards in 2022. Fresh out of Covid and tied to a boobing baby, I knew almost noone. 2026: I booked a table for a group of us and celebrated with a room full of colleagues and friends.

It’s relationship building.

You never know what new friendships and peers are waiting for you!

Particularly applicable for the the Assistant industry here - it raises our profile

And frankly we need to.

We know as an industry we have long been overlooked - but thriving awards full of brilliant Assistants and businesses founded and led by us.

What better way to showcase we are here and not going anywhere?!

To end on a personal note: I’ve noticed in broader awards for growing service based businesses and their leaders, our industry isn’t getting recognised.

Yes, that means I’ve applied to (many) service industry awards and not been longlisted. But this isn’t about my own ego and Upsource not getting recognised. If I saw my colleague agencies winning, I’d be happy and see it as something to aspire to.

But they aren’t.

Especially the female AND actual former Assistant led ones. (No idea if they are entering awards, but I sure am.)

I know what we have achieved as a business, what I’ve achieved as a solo founder, the results we create for clients and team members. So I’m ending with my rallying cry to get the Assistant industry more widely recognised in wider awards.

If we are all entering, ONE of us has a chance of getting recognised right?! So be part of the movement - apply to some awards!

I’m interested to hear your thoughts and experiences on this one. Continue the conversation with me in the comments.

Leave a comment

Awards actions:

• 28th February: Deadline for Midlands PA Awards entries. Info here

• 30th April: UK VA Awards 2026 applications close. Get the application pack here

• Spring: Global PA Awards applications open

Make sure you’re subscribed to receive our full monthly digest - more awards to enter, networking and coworking events to attend, and opportunities to upskill.

Subscribe now

Next Steps:

• Listen to my conversation with Deb Gilbert, founder of the Best Business Women Awards on why awards have been so central in building my business and network. Follow Deb everywhere - she runs some great events too.

• Strategic PA Network have just launched their mentorship programme 😍 Mentees will gain clarity, confidence and perspective.
  Mentors will rediscover their purpose and sharpen their leadership skills

  If you’re interested in becoming a mentor, or being mentored email hello@strategicpanetwork.com for more info

Questions/Comments:

Full transparency - I’m testing my theory and have applied to the HSBC Small Business Growth Awards. Let’s see what happens! Let me know, what awards are you applying for? Have you noticed any, strong word here I know, discrimination against the Assistant industry outside it? Let’s take it to the comments.

Leave a comment

Suggested Reading:

• If you haven’t already, check out Lucy Werner’s Substack, and her book Brand Yourself, to help you frame how to speak about yourself and your business.

F*ck up of the month:

Paying my Corporate Tax to my personal tax account - what a headache 😭

AOB:

Upsource is looking for a new team member with experience in start up sales. Is that you? 🫵🏼 Click here 🫵🏼

Speak soon,
Caroline x

When you’re ready, there are a few ways we can work together:

Click here: If you’re new to the Assistant world, and want a webinar that shows you how to create strong business foundations

Book here: If you want an hour’s chat with me to help hone your business

Click here: To sponsor this newsletter, or the Bump to Business Owner podcast and connect with 1000s of women, mums and business owners

Leave a comment

I am proud of Upsource, every single team member past and present, our work, our clients, our commitment, our wider community (that’s you!) and my healing and growth journey to get here.

Here’s to the next 5 😉

Points of Business:
5 lessons from 5 years as an Assistant agency

5 years has taught me a lot, about business, about myself, and especially about stepping up from an Assistant into a leader. I’ve shared my wider 5 learnings from 5 years in business, but these are the 5 learnings that I believe every PA / Assistant / Admin professional will go through to step up their growth and step into leadership. Whether you’re looking to lead a team in your current role, or create your own agency, these 5 things will help.

1. Challenge yourself to really understand yourself (especially your weaknesses)

Your real weaknesses. I’m not talking about ‘I’m not into minute taking or wild about inbox management’ Those are  a given.

I'm talking about triggers from your past, why you are you, hormonal cycles (if you have them) your stage of life (lack of sleep with little kids?) Why? Because you are growing your business to work with people and all people have problems. 

People bring problems. And you have got to be ready to deal with them with empathy. 

Will you get it right all the time? Absolutely not. But knowing your triggers, will help. Trust me.

2. Don’t get distracted by shiny things and what others are doing

A course that will bring you £20k months working 4 day weeks?

A VA coach who had 6 figure months within a week and will show you how to do the same?

That agency owner who now works 2 hours a day in the Maldives sipping margs? (Where did I go wrong 😂)

There is a  lot of BS out there.

Those are extreme examples. But trust me, everyone’s shiny exterior looks very different to their reality.

Building a business is work. If there was a ‘secret’ to not working and earning ££££ money - there would be a hell of a lot more people doing it. 

Focus on YOUR goals. YOUR dreams. Find the people you can learn from and who will support you through it. Don’t obsess over other people’s dreams, goals and ‘Instagram realities’.

3. No one else is YOU and stop hiring ‘better than you’ (controversial)  

No one else is you, and that’s a great thing.

BUT. You really need to know, no one, no one cares about the business the same way you do. And that is key when bringing on team members - what are their drivers?

I regularly hear ‘I want to hire people better than me’, ‘I only hire people better than me’.

I am calling that marketing BS.

Frankly not everyone is going to be as good as you. Will they be much better at handling some client personalities, or much more skilled in an area you just aren’t great in and don’t care to improve at?

Absolutely.

As an example, the amount of times I’ve had clients come to us that are great clients for Upsource but wouldn’t be for me 1:1. I have found a much better personality fit for them.

But going into hiring, looking for people ‘better than you’ is a mindset that sets others up to fail. That’s the last thing you want.

4. Working ON your business - even the really unsexy, boring stuff

Many many people will tell you this, there are many courses / coaches who specialise in this.

But, frankly, it’s true.

Want to grow your business? That won’t happen if you fill all your hours with billable time and never make time for you.

Half day a month
A quarterly away day (with yourself and your laptop 😍)
A bi annual solo work retreat

Whatever it is - schedule it, guard it like a hawk.

5. Keep on learning

I had lunch with a friend recently, and we got onto the subject of how to foster a learning mindset. I did a course with her last year (Fiona from Carve, check them out!) and she said she could tell from my approach to that course, that I lead Upsource with a learning mindset. 

(Sorry, blowing my own trumpet there)

There will ALWAYS be things to learn. We are living in an AI world; clients want us to be taking advantage of it. (Not all but most - I see a lot of founders with AI FOMO.)

But get uncomfortable. Think you are techy? Hang out with VAs even more techy, and see if you can learn something.

Spent 20 years supporting CSuite leaders in corporate? Hang out with some Startup VAs to see the differences and similarities in how you work.

It’s been 5 years at Upsource but next year, I will be almost 10 years in supporting startup businesses and I LOVE their mindsets around learning, it’s addictive. 

Actions:

• October 2025: VA Conference and Awards. Ticket sales are open

• 3rd November (ceremony): Strategic PA Network awards - open for nominations. I’m on the judging panel this year, for Networker of the Year. Get nominating!

No separate dates for your diary email this month as everyone takes a well earned break over summer. It will be back at the end of August with a load of exciting events for proper Back to School vibes. If you’ve got an event, conference, coworking, training etc coming up that you want me to shout about, send me a message to get into the next issue. 

Next Steps:

• Speaking of learnings, learn from (more of) my mistakes - don’t waste thousands of pounds on internet hype.

• If you’re just starting out rather than scaling, here’s what you need to set up as a service based business.

• Another resource if you’re setting up your Virtual Assistant business, Your VA journey: Start Here

Questions/Comments:

Did any of those learnings give you that ‘been there’ feeling? What have I missed? Let me know. 

Leave a comment

Suggested Reading:

Looking for funding to support your VA business growth? Here are some helpful places to look and some advice from female founders who’ve been there

F*ck up of the month:

I had created some quite important timelines for the team months ago.

And wrote them down...nowhere. A huge error when scaling, and juggling tight deadlines!

Thank GOD for AI - I had recorded the calls where I had verbally confirmed the dates. AI literally saved me and not for the first (definitely not the last!) time.

AOB:

A huge thank you to all the Upsource team past and present who have got us to 5 years and keep choosing to work with us 🫶🏻. We had a gorgeous little birthday party at the start of the month and it was wonderful to meet some of the team IRL!

And, as always, if there’s something you want to hear more about, especially if there are specific areas where you want to upskill, put it in the comments so I can write a newsletter especially for you.

Leave a comment

Speak soon,
Caroline x

P.S. Please do share this with any Assistants that you think might benefit