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“Well, good luck and let me know if you need anything.”

I was having a final conversation with my manager. It wasn’t supposed to be like this. The role I’d thrust myself into over the last six months hadn’t worked out the way I intended and we were parting ways. It was bittersweet. Throwing myself into a creative agency and figuring out the world of startups was a dream of mine but somewhere along the way it failed to meet each stakeholder’s expectations.

It is now a week later. There are irons in the fire, and I’ve been hustling my arse off to get the right kind of work, add value, and find my place. In the last week I have:

  • Reached out to at least 32 contacts
  • Received 3 rejections
  • Travelled to 14 meetings
  • Had 3 interviews
  • Popped in 5 job applications
  • Received radio silence from at least half a dozen contacts (more on this later)

Leaving a job with nothing to immediately move on to is risky, financially taxing, and not for the faint of heart. It also forces you to be creative, hit the pavement, and challenge yourself in ways you don’t expect.

In this article, I’m going to detail my experiences and learnings from a week in the wilderness.


Positioning yourself

I’m a digital generalist in the wilderness. My roles have been varied, and I’ve adapted to what has been required in every role I’ve had. This has seen me implement social campaigns. It’s seen me pitch multi-million dollar sales solutions to C-suites. It’s seen me get under the hood and look at analytics. It’s also seen me become a jack-of-all-trades that makes it harder to slot me into a job description than say, a mid-weight designer.

This isn’t necessarily a problem for people, but you need to be able to put a story behind it.

  • Applying for something with PPC and social? Play to your digital marketing expertise.
  • Meeting a strategy agency? Impress upon them examples where you’ve thought at a higher level.
  • Applying for a business development role? Talk numbers and how you worked to hit them.

As your career matures – you might find a particular patch that resonates with you. For me it’s client services and business development, and so I’m working hard on tapping into that area of the market. We’ll see what comes of it.

The next thing I needed to do, is ask for help.

Tapping your network

The first place I turn to when I need help is my family and friends. So initially I let my personal network know. Facebook made this easy. I wrote a polite note, and mentioned that I’m on the lookout for opportunities to help. I didn’t expect this to convert into job prospects, but the chance to connect and help some friends out while I’ve got some spare time was something I didn’t want to pass on. As a result, I got to catch-up with some dear friends this week and catch some quality time between meetings.

Thank you note on Facebook

Now friends and family are great and all, but when it comes to work, my professional network is whom I’m going to call upon to get shit done. It’s tempting to carpet-bomb a BCC list at this point, but I think it’s impersonal and unlikely to drive a high number of conversions.

What I mean by conversion in this instance is someone replying to my outreach.

Instead, on my first pass at the start of the week, I wrote to 15 or so contacts with a personal request for help. These people were either my go-to people, or interesting people I’d met along my career that I’d kept in touch with.

I did this via their work or personal email, which I had from previous correspondence, or sourced from their LinkedIn profile. You can get most of your connections’ email addresses via the ‘Contact Info’ button on LinkedIn.

Contact Info LinkedIn

My response rate was around 90% using this approach. Which is a better result than a carpet bomb. It’s also a more considerate way to use your network.

What to do when they respond

It’s the nature of the networking game – but there’s going to be back-and-forth getting times in the calendar. The fortunate thing is you’re more available than them, so going to where they are based, giving them a range of times, and being patient are all key and a part of the game.

The meetings will start lining up – I would commit to no more than 3 a day to allow for travel (dependent on where you are, and whether you’re relying on public transport or have a car of course).

The in-between zone

There’s stuff you’re going to need to do in between meetings. Research, writing applications, taking phone calls, and personal admin. Remember to be kind and not overstretch yourself. A few guidelines I followed were:

  • List what you want to get done the day before or in the morning, keep it short and allow for things to bubble up as opportunities change over time.
  • Make the things you’re doing achievable and celebrate crossing them off – it can be disconcerting being out of a gig – but a small win is a small win
  • Camping at cafes is fine. I always purchased something (even if it was just a peppermint tea) – not doing so feels like a jerk move and you’re using their space


So what do you do when you actually meet your contacts? I’m not going to pretend to know every social nuance or dynamic you need to follow, but here were 3 things I tried to do:

  • Get your story straight – people generally want to help you. You’d be surprised by what your contacts can do for you, but you need to have your story bolted down before entering the room. Be clear about what it is you’re after, what’s on the horizon, and manage expectations accordingly. If you’re still thinking about what it is you want then be honest about it. But also be respectful of the contact’s time and have something in mind that they can specifically help you with.
  • Ask for advice – you’ve reached out to a contact, you’re wondering what career opportunities are out there, and you’re sitting in front of someone that you respect. Ask them what they would do! If it’s a close contact, they’ve got an idea already about your skill-set and how they’d attack your challenge. If it’s somebody in a different area, they might have an interesting new take on what you could be doing. Bring your notebook and note down what they tell you as it’s usually gold.
  • Ask for a referral – this is one of the differences between okay networking and great networking. You’re meeting someone who also has a network, a network you don’t have full visibility into. A polite “do you know anybody else I could be speaking to?” will help open new doors, and build out the list of people you can be contacting. Smart people know other smart people.

Also, be respectful of the other person’s time! They’re more than likely taking time out of their working day to meet you, so don’t monopolise their clock. Try and be self-aware and read the play here.

You got some new intelligence, a page full of notes, and a steer on what your next move could be… follow-up! Dropping a note within 24-48 hours of meeting the contact, thanking them for their time and recounting any info shared is super-courteous. This could be linking them to a book you mentioned, sharing the contact details of a person you mentioned, or agreeing to meet at another time. You’ve involved the contact in your journey so keeping them posted on your movements is a good move.

Also be on the lookout for what could blow someone away. I remember helping out my friend with some career guidance late last year, as she was curious about networking overseas and picked my brain on a few things. A few weeks later, I had some flowers delivered in the mail with a handwritten, personalised thank you note. Do you think I’ll help her again? Share the love!


Whenever I have an interaction with somebody, I like to think, “what does going above and beyond look like here?” When the stakes are high and you’re on the lookout for the next opportunity, you should be asking this question daily. Below are some methods I’ve encountered and used to really try and stand out.

Reactivating your old connections

Beyond your immediate professional network, there are people you’ve been in contact with that you’ve probably forgotten about. I did some consulting work a few jobs ago, and didn’t even think to contact some of the people outside my immediate industry. It was only after chatting with another of my contacts that the thought occurred that I should reach out.

A quick search of your email (and older email addresses) can turn up some gold. The beauty of this approach is that you’ve got a lot to catch up on, and because you have lost contact – there might be some things they can update you on that surprise you!


There’s no doubt that an existing connection, or a referral, are going to provide you with much higher converting opportunities. With that in mind though, you should be contacting people that you think could:

  • Get some benefit in their life from meeting you (always be adding value first); and
  • Help you along in your merry quest to find opportunities.

It doesn’t matter how often you put yourself out there, it’s always a little bit scary. There are ways you can increase your chances though. Here’s what I think works:

  1. Find a common connection
  2. Reference something they’ve done or how you’ve come across it
  3. Keep it short
  4. Tell them what you want (and where you can add value)

It’s not going to work all of the time, but sticking to the above four points will help increase the chances of getting a response. With his permission, I wanted to share a request that Caleb used to introduce himself a while ago:

Outreach Note

Caleb noted my love for Singapore, mentioned he’d spent some time there, explained where he found me, and asked for some help. We had coffee and if you can help him too please drop me a note.

Keep in mind though, that not everybody is going to respond to you. Some people are busy, aren’t clear on what you’re after, don’t think they can help you, or have any other myriad of reasons for not responding – please don’t take it personally – just saddle up and move on to the next approach.

Designing your job application (for non-designers)

I’m a big fan of putting a lot of effort into the job application. I work in digital marketing – if I can’t stand out from a crowd as myself, what hope do I have while guiding brands? With that in mind, I usually like to put together a bespoke application for the role. I’ve done this a number of times, and have almost always secured an interview. What I’m about to share will probably make designers cringe – but it opens the door and gets things going.

Did you know you could create PDFs in Keynote or PowerPoint? It’s not InDesign, but they do the job and can get doors open.

Here’s an example of a leave-behind I did when I was in New York.

New York 1 Sheeter
And just last week, I interviewed with an agency that I wasn’t quite the right fit, but got the interview with the following deck.

[slideshare id=64550575&doc=howicanhelpaugustwiththeirdigitalmarkeing-160731081312]

There’s a few more you can find here.


Well it’s a week in! There’s a lot to follow-up on, more pavement to hit, and opportunities to create. The response has been overwhelmingly positive so far, and if you’re one of the people I’ve come across the last week – thank you!

I’m going to keep applying what I’ve learned and look for the next opportunity that’s right for me.

If you want to have a coffee, think you can help, or want to work with me, please drop me a note at

Thanks for reading! If you liked the article pass it on to somebody you think might like it or give it a share to your network.