Grow or stay small? 5 Essential questions all freelancers should ask

Grow or Stay Small

Do you ever sit back and wonder what you ultimately want from your design business?

What does it look like 10 years from now? Staff, money, cars, house, turnover, clients, holidays, boats, helicopters, happiness and the list goes on.

I’ve been on a bit of a roller coaster lately, not by choice I can assure you. But it’s made me ponder what I actually really want from my business and my life.

💔 Falling out of love with your clients? Trade some of your worst clients for the best companies in the world with SolidGigs, our premium weekly freelance job list & course library. Love your business again. Learn more »

I found that it’s so easy to get caught up going in circles on the hampster wheel just to get to that next stage. Yet sometimes we forget to stop and re-evaluate whether we’re still in alignment with our dreams.

(A plug from Preston: PS, Don’t forget, we’ve only got 35 spots left in Stoked this month. Claim your spot before it’s gone. We’d love to have you on the inside. Learn more here. Ok, back to Bianca.)

I can tell you from my recent experiences, it’s not all smooth sailing at the top and it’s definitely not for the feint-hearted. You think you’re cruising along going great guns when BAM, something blows up.

A friend of mine who sold his business for $21m said the stress is the same even at that level. You have the same issues day-to-day and you still struggle with cash flow… you just add a couple of zeros at the end. 🙁

Enter your email. Grow your business.

Submit your email below and join 45,000+ creatives who get our most helpful content via email every week. 100% free. Unsubscribe anytime. Privacy protected.

So the question is my friend, what is it that you really want?

Here’s 5 Tough Questions To Help You Decide Which Road is Right For You

1. What is the maximum you can potentially earn as a freelancer?

Now, ask yourself: Is that going to be enough for me to reach my goals.

Lots of designers don’t want to become multi-millionaires and that’s absolutely fine. Others however (not mentioning any names *wink*) want to buy a luxury boat with an ice maker and cruise around the world. There’s no right or wrong, just what YOU want!

Let’s say for argument’s sake that you turnover $150,000 per annum and profit $1,000 per week after all expenses are paid. Would it satisfy your desires to be stashing away around $50,000 per year in a savings account? I think that’s pretty damn good let me tell you!

If saving $50k a year floats your boat then put a tick next to #1. If you want more than that, and you can’t see a way of getting it as a solopreneur, put a cross.

2. Where do you want to be 10 years from now?

Close your eyes and visualise your ideal day. What time do you get up? What’s your morning ritual? What time do you start work? Do you still work these hours? How many days do you work?

What is it you would absolutely LOVE to be filling your time with 10 years from now? For me, it’s writing, sewing, painting, gardening, cooking, designing, creating, helping and doing a lot of charity work and so on. I know I still need to be stimulated though so I want to work 2 days a week on my business but have a CEO to manage the day-to-day.

Do you live by the beach or in the countryside? Have you got kids? If so, how many? What do you do with all your time? Are you still designing?

You might decide that charity work is the direction you want to take.

I know there’s some tough questions there that dive deep into your life’s purpose, but it’s important to evaluate what you really want before you decide whether your business can take you there in its current form.

I love my business and I love what I do, but I also want to use my business as a vehicle to do other things. I’ve had this big hairy audacious goal (or BHAG) for years to build 50 orphanages around the world by the time I’m 50. I know that if I’d have stayed small, I wouldn’t be able to reach that goal funding it myself so my business is a big part of my purpose.

Figure out where you want to be in 10 years and put a tick if staying small can get you there and a cross if you need to grow big to achieve your goals.

3. Do you enjoy stretching yourself and learning new skills?

Does change stress you? You’ll have to decide if your big goals are worth the potential stress of evolving from a freelance designer to an entrepreneur. Because I can tell you, growing big is STREEEEEEEESSFUL! It’s a roller coaster on most days too, not just when the going gets tough. You learn how to roll with the punches and go with the flow but it is challenging.

You need to be the type that can cope with change easily, make decisions fast, show true leadership and get back up quickly every time you fall flat on your face. And you will make a lot of mistakes, trust me. Like I said earlier, it’s not always smelling of roses when you have 20 staff members and a healthy turnover, let me assure you!

If you go big, you’ll probably have to take a step back from designing as much as you are now.

These days, I run the day-to-day operations of my business, I lead my design team, provide feedback, suggest new ideas and only dabble in a little bit of design. The reality is that I’d rather be doing *just* design work, but running your own business means you need to focus on all areas of your business.

If your bliss really is designing all day long, then perhaps growing big is not for you. If on the other hand you still want to keep your hand in design but are prepared for it to take a backseat, then I’d say taking the bull by the horns and growing big could be the right path for you.

4. What do you love and hate about your business?

First list the top 10-20 tasks you love in your design business. Now list the top 10-20 tasks you hate in your design business.

So now you have a solid list of tasks you love and hate,  just to the right of that, work out what can and can’t be delegated. The trick here is you’re going to need to factor in outsourcing or offloading all the tasks you hate so you can focus on what you love doing.

The only thing you can’t outsource is growing your business. No one else is going to make it happen!

If your list is all design and no business then you might find the shift from business-owner to business-builder a tad painful and not the right move for you. I’m heavily driven by business and design, not just design so naturally I found it easy enough to let go of it. Although I still love designing and it makes me happy, I get enjoyment other ways day-to-day.

So how’d you fair? Are you 90% design and 10% business? Or 50/50?

5. What makes you happy?

Another close friend of mine who happens to be a life coach, said to me recently:

“Think about what made you really happy as a child… that will give you the answers as to which direction you should take in your business and life. And maybe it’s not even web, maybe it’s something completely different…”

You can imagine how much my head was spinning but it got me thinking. I thought back to my childhood days and realised that I absolutely love making stuff. I love the process of creating something tangible from nothing.

As a kid I had a stand at the Sunday markets selling crafty stuff I’d make myself. Later on I got into creating dried flower arrangements. Then knitting. After that it was my local Lapidary Club where I’d carve and polish precious stones to make jewellery, and after that was painting and selling art.

Looking at my life now, I guess graphic and web design was a natural progression once I grew up. Nowadays I get a lot of satisfaction out of helping people like you, and creating content like blogs, courses, videos, programs and eBooks etc.

But is it my true calling?

I’m still pondering that one, as a lot has changed lately, but instead of looking at the cards that were recently dealt to me as a negative, I’m looking at them as an opportunity to evaluate what I truly want and what really makes me smile.

So what makes you happy? What gives you that buzzy feeling inside and a smile from ear to ear as you fall asleep at night? Maybe it’s not even design! Who knows. We’re all special and unique with unique gifts to offer. You as much as me, as much as anyone else on this planet.

I can tell you that I don’t regret growing big but at times I do question what it would have been like staying small. Sometimes I want to run away from all the stress and other days I love what we’ve created and couldn’t be prouder of what I’ve achieved.

So tally up your scores, give it some thought and let me know which direction you’re considering in the comments on this post! I’d love to hear your plans! 🙂

Keep the conversation going...

Over 5,000 of us are having daily conversations over in our free Facebook group and we'd love to see you there. Join us!

  1. Up until certain extent, we will have no choice but to grow.
    If we stay what we are, we are actually going backwards.

  2. You have definitely got me thinking about my own future, and how I see myself in 10 years time. Whether staying small, or growing big, life is definitely not a bed of roses.

    All the best to everyone…and remember to stay true to yourself!

  3. Oh my Gawsh!!!! Now I am more confused than EVER. Great post. I will have to take some time to ponder these points. Im not sure I have the courage..

  4. This comes at such a time I’m thinking about the future having taking holiday to anaylise ‘hill and valley’ experience in my business. This has helped widening the horizon.

  5. These are very interesting questions, and ones that most freelancers that I know don’t always think of asking. It’s like you said at the beginning – you just get on the hamster wheel every morning, and run in circles until you get off at night. You don’t stop and think about where you want to be in 10 years, or even 10 months. It’s very hard, certainly for freelancers who have just started out, to think where they want to take their business to, and how big they should (or want) to think when going ahead. By the way, in my experience, part of the problem is finding jobs. So many freelancers are tied up looking for their next gig and their next client,and they just don’t have the time to lift their head up and look forwards. Instead of signing up for websites like LCKCenter ( to get noticed, they spend a whole lot of time hunting around for new contracts. If you can get past that hurdle, and have clients find you, then you can spend more time thinking about how to develop your business.

  6. Some good questions, only I’d start with number 5 and work backwards from there. If I’m happy I’m more productive, so I do more of that, as little of the stuff that doesn’t make me happy as possible and from there flowed my earning potential.

    I now know how many weeks in the year I have to be working on projects to meet my financial goals, and this has given me space to cherry pick more of what I want to do and a lot less of what I don’t.

  7. This post literally could not have come at a better time. Beginning next month, I’ll be revamping and re-evaluating and changing direction a bit with my business and life as a writer, especially on the freelance end of things. This post has given me some food for thought and I’m going to do some journaling and brainstorming on these questions in the next couple of weeks to see what shakes out.

  8. Good read.

    I have been thinking about this for a while. In order to get to the place I want to be I will need to develop a team. Work is steadily increasing and I will soon need some help. However, I am not sure where to look for reliable and trustworthy people. I definitely want something that can grow and evolve long after I’m gone.

The conversation's still going in our free Facebook group . Join us there!