How to Expand Your Creative Business: The ‘Daily Drop-By’ 30-Day Challenge

Landing new paid work for your creative enterprise can be bloody difficult.

Whether you run a bigger creative company or you are a part-timer artist, the biggest challenge very often is to win new assignments or commissions.

You’ve chosen to be your own boss rather than work under somebody else’s rules. I hear ya. The freedom to decide when and where to work under your own terms is a delicious idea…

…But with freedom comes the responsibility to ensure you actually keep getting paid.

The whole promotion thing never seems to get comfortable or any less of a pain.

Especially if you provide a service requiring clients, you’ve effectively opted into a world that requires you to get a new job, not just once, like many of our employed friends, but several times a year, or even many times a week.

I know how difficult it can be to keep getting paid. It can seem like a never-ending task to drum up new client projects consistently. You want consistent income after all, yes?

But I know the alternative. And this is to work for someone else, in a much more constricted environment, without the flexibility to work anywhere and whenever you want.

So we need to make this work. We need to keep getting paid well, and we need to do what it takes to do so. This means that we make ourselves known to the world through promotion and marketing. There is no way around this if you want true freedom in a client-driven business.

Is Self Promotion Really Necessary?

Many of us say we struggle with lacking the time needed to promote ourselves.

Creating takes enough time as it is. There’s little energy left over from making art, to then go out and promote, or at least try to. How can you be expected to make art, and then go around telling everyone about it without coming across as a schmuck?

Surely it gives off a desperate vibe? Isn’t self-promotion something for untalented (and somewhat unsavoury) types anyway?

If you make truly quality things, you shouldn’t need to promote yourself, because the art should speak for itself, and people will find you… right?

I’m going to pop that delusion for you.

Everyone who takes their creative business even remotely seriously needs to embrace promotion, i.e. Actions associated with generating awareness to one’s name, work and brand (which ultimately leads to paid work).

You absolutely must take regular action to ensure new projects from the very best clients you can find, come to you.

And I’m personally crap at this. I know it doesn’t come naturally to any of us.

Most of our ‘reasons’ for not promoting ourselves are excuses.

Most of these excuses are lies.

That we don’t have enough time is a lie. We all have enough time, and we all know this deep down.

All of these excuses come from a lack of clarity. All fear and confusion stems from a lack of clarity.

So the solution is clarity.

Everything becomes easier when we are clear on what we need to do. Most of us – even some supposed professionals – haven’t got a clue about how to promote and sell properly. We lack the knowledge and clarity, and this leads to action NOT being taken.

Such procrastination creates the illusion that we don’t have enough time, and we end up relegating to the sidelines the important stuff even more.

We all have more than enough time to act, when we know what to do and we spend our time cleverly.

Today I want you to challenge yourself.

One of the things I’ve discussed a lot on Red Lemon Club is the power of setting ourselves challenges to create a greater sense of urgency and generate a surge of energy inside us as we tackle our tasks.

If we’re off track with our promotion, we need to get into the right habits.

In my view we struggle to take the right action because we don’t do the things that work every day. The weekend rolls around and we lose momentum.

So the challenge is really one of consistency, rather than a complex task per se. I want you to do one thing every single day, over at least the next 30 days that will move you forward in your marketing.

Important things, like those things that help build your network and get your brand out into the world, are worth doing every day…

What to do every day for the next 30 Days

If you’ve read any of my books and courses, you’ll know that I consider the one-on-one relationships you have with people in your network to be the most important aspect of your self promotional strategy.


The ‘Daily Drop-By‘ Challenge:

I want you to reach out to at least one new person every day for the next 30 days, and see what this can do for your business and your confidence.

This includes weekends and trips away…

What opportunities will come from talking to one or five or twenty people every day and simply asking for help, for 30 days (and hopefully you won’t stop).

Many of you find it really hard contacting complete strangers. I agree with you. This can be a challenge. Finding their contact details for a start and then working out what to say can be hard, feel awkward and take time.

For this challenge, I want you to only contact people who already know you, whether they’re a dream client or not. They can be anyone you know: teachers, past employers, people you met at a conference, colleagues, people you had a Twitter conversation with, old school acquaintances, and so on.

I won’t talk much more about who is best to talk to beyond telling you that the more awkward reaching out to someone might feel, whether through a phone call, an email, or social media, the more likely they could lead to a fresh opportunity for you, and at the very least build your self confidence.

So make a list of people who know you, or dig them up. Find all those business cards you’ve accumulated that sit in your drawer and get them out.

It doesn’t matter who someone is, and how seemingly powerful and well-connected they might be right now. The challenge is to get into the habit of contacting people. I also want this challenge to show you how many opportunities lie with a range of people of all kinds of backgrounds, even if they aren’t obvious target clients. You might be surprised at what you find.

If it frightens you, start simple. Start easy. Contact your mum or your brother. You might find that even they know people who can hire you, because you’ve never asked them or mentioned it before.

The challenge is at least one new person a day, but the more you do the better. It’s a numbers game as well as a game of connecting with human people.

What stuff should I say to them?

Be honest. Tell them that you’re looking for opportunities, and want to ask whether they need your services or if they know anyone else who does. Tell them to name one person who might be able to help you. Maybe you just want to reconnect and not even mention that you need work. Experiment.

Drop the fear and just do this. More often than not, people will be impressed and appreciate the fact that you’ve bothered to contact them.

Doing this daily is what’s important. It’s the consistent action that is the most important part of your promotion strategy, NOT what you say. Get into the habit of talking to people and driving through the discomfort of worrying about what people will think of you.

Following up with people is also important, because it dramatically increases the odds of a response or someone following through with a question or request you have for them. You can follow up within the month, but they don’t count as daily contacts.

Next month you can also focus on following up.

The ‘Daily Drop-By Challenge’, once more:

Communicate with at least one new person who already knows you, every single day, for the next 30 days.

Rules and tips:

  • Feel free to use any medium for this, whether hand written letter, email or phone call (most effective!), as long as you are sending something tailored specifically to that person.
  • Sending a written message to someone counts as communicating with someone, though actually speaking with people will tend to be more effective. Following up plenty will also increase the likelihood of seeing results.
  • Mentioning common ground between the two of you, such as an event you both attended, is a great way to break the ice, and create trust.
  • Allocate a defined chunk of time each day to do this without distraction. It need not take more than 5 minutes per person.
  • Follow ups to the same people don’t count as your ‘one a day’, but they are encouraged to make this really effective and many will have a back and forth with you anyway. But sometimes people won’t do what you’d hoped, like link up someone they know to you, in which case a follow up is important – even three or more follow ups within a month. Push it, don’t hold back.
  • Know why you’re doing this. Your business and income is important for your survival, growth and in supporting others around you. You are taking a stand to change things and it is vital that you get this aspect of your career right.
  • Do additional promotion stuff if you can during this challenge, like posting and engaging on social media, sharing blog posts, sending postcards, etc. The more the better, and you will tend to get added motivation to do more when you take the small steps in this challenge.
  • You can use the same copy and paste template as long as you adapt that template to the person receiving. In most cases this would require a from scratch message anyway.
  • Offering help in exchange for them helping you is also a good idea. This is win win, but simply asking for help is perfectly fine.
  • Talk about anything you like, but I’d encourage you to ultimately get to the topic of paid work and finding people to hire you for your services. Be brazen and bold about simply asking for work and asking for help.
  • The more of this you do, the more feedback you will get, and the more effectively will be your communication methods into the future, so I will leave most of this to you, and just encourage you to take action.
  • When and if you have completed this challenge, you can move on to other people who don’t yet know you, dream clients, etc. You can also start doing this within the 30 day challenge, but you must make sure to stick to the 1 new person who knows you rule.

Example of what I might ask someone I know:

Hi Frank,

It’s been a while since Fuji Rock festival 2012, and I wanted to check in and get your help with something. You well? I’m in Bangkok right now enjoying a new environment away from home and really liking it here (apart from the insane heat).

I’m looking for more opportunities for my illustration business, and want to know: is there anyone you can think of who would benefit from my artwork in their business? If you could think of one person you could link me up to, who would that be?

The link to my portfolio, as a reminder, is below.

Let me know!

Thank you pal,


Note: You’ll notice that in the above, I’m asking Frank if he knows someone who could potentially hire me. The more astute among you will notice that by asking for a referral, I’m also advertising my service to Frank himself, albeit indirectly.

Takeaway: you can promote yourself to a potential client by asking that person for other clients too.

– –

My big question: What is the ONE THING that holds you back the most from doing a challenge like this?

Comment, and I’ll respond.

I want to hear about your experiences as you go, so do comment below about everything and anything you experience as you do this and I will be here to discuss as you go along.

Contact me here for help also.

Bon Voyage!



  1. This is so simple and practical but so easily overlooked. I’d say what holds me back is feeling as if I’m being a burden to them. Like they see my name pop up in their inbox and they think, “I thought we were done?”

    I’m sure it’s not that way and I’ll soon find out. Thanks!

    • Totally agree. My advice is to understand your value. If you know that we you do can benefit someone, then it should be seen as your duty to get it in front of those people. See success as your moral obligation. Take it to a ‘higher level’ – be bold. Don’t focus on what you cannot help someone with, focus on how you can help them, and be persistent. Report here on your progress. Would love to hear more. Alex

  2. Love love love this! I’m one of the people who always thought that, once the ball is rolling, you will never have to promote yourself again. I love to read it’s not just me who has to keep going after jobs…
    To think about people who already know me is a real eye-opener in this post. I thought about it a little, wondered if it wouldn’t sound too desperate. Then dug through my email and noticed I could easily do a few follow ups with people I talked to months ago. Which is just being nice really, asking how the vacation was and such. And who knows what is will lead to!
    So what was holding me back is that I never really gave it that much thought. Thank you Alex!

  3. I’m a cartoonist and I’ve always felt like I’m needy when contacting potential clients (or I’m bothering them). I always expect that email back saying, “Quit annoying me!”…but that has never been the case. Great post! I’ll give this challenge a shot.

  4. As An artist i just live in my own hidden world. I need that to create work. I know i need to go out, i am not shy, but yes i feel deep down somewhere that iTS a bit like begging… For money.. That they like my work. When i just finished art school i was so insecure, and i promised myself that i would never ask people to like my work.iTS that part that makes iT so difficult. Selling a product is so different then selling a piece of art, An idea, yeah a piece of yourself..

  5. Ha,ha! I just used the word “clarity” today, because after a million years of being a thankless reader of your book called “The Indispensable Illustrator”, I decided to be thankful and write a well-deserved review on amazon, which I finished by saying “I would recommend this book to any freelance illustrator looking for clarity in their career.”
    And speaking of clarity and another post of yours regarding great quotes, I think this one by Steve Jobs nails both subjects: “Your time is limited, so don’t waste it living someone else’s life. Don’t be trapped by dogma – which is living the results of other people’s thinking. Don’t let the noise of others’ opinions drown out your inner voice. And most important, have the courage to follow your heart and intuition. They somehow already know what you truly want to become. Everything else is secondary.” I have this quote floating above my desk…

    To the topic of self-promoting, count me in with one friend contacted yesterday and one other person today. I illustrated a love poetry book written by my sister-in-law and it looks like the best audience are people that are getting engaged or married, since this is a potentially good gift for them. So I asked my friends to remember my book every time they know of someone getting married/engaged.

    Thanks again for all you do!

  6. Hi Alex,
    Thanks for the great article! I found the stuff on your website to be very inspiring. It really does nail a lot of things that I’ve been chewing on in the back of my head. I find it to be really rare to read something that makes so much sense and would like to let you know that it’s greatly appreciated!
    I decided I’ll give the challenge a go. I have a problem though. You mentioned it very precisely in your article about consistency in marketing – one about fearing to market so that you have too much clients you can handle. I’m an illustrator and I’m in a place you described: I have enough clients to be fine financially and that makes me hesitant to network and promote out of fear I’d actually let people down after additional offers. I’d really want to grow my small business, but not exactly in terms of having more clients for comissions, but rather in creating more content of my own and making a living out of it, like prints, comics etc. I still feel like I’m too small in the world to make this possible.
    Would you happen to have an idea how to use this one-a-day model towards reaching this kind of goal? I’m really pumped and would love to give it a go, but I fear just simply having more clients wouldn’t do the trick for me.
    Thanks a ton for what you’re doing!

    • Hi Kuba – totally understand. This approach does not just apply to winning more clients, but also customers for products. Beyond obviously sharing a new piece of content daily for attracting new fans and followers, you can reach out to new people every day who have audiences of their own who might be interested in buying your own products. For example, you can talk to bloggers and influencers who can eventually share your content with their people. You have nothing to lose by communicating with people daily. Good luck!

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