Whether searching for work, cultivating relationships for your business, managing relationships in the workplace, or creating a following through social media, you need to master important writing tasks.
This post encourages you to:
1. Make writing a game – have fun with it.
2. Practice writing in low-risk contexts for high-risk challenges.
3. Draw on internal and external resources to support your writing.
Read on to learn more.
1. Make writing a game – have fun with it.

Writing about yourself is not easy. Yet for important transitions such as applying for a competitive education program or plum job, it’s necessary.
Why is writing about yourself so tough?
Perhaps you are someone who knows so much about yourself, it’s hard to decide what to say, so you feel overwhelmed. On the other hand, maybe you don’t really know yourself well, so struggle to find something interesting to write about. Then there is the uncertainty of not knowing who our readers are or what they want. We can’t read their minds. So we hesitate and procrastinate on our writing goals.
These challenges are normal, so don’t beat yourself up. Instead, turn your writing tasks into a game – one that has players, rules, sometimes time constraints, often both prizes (the offer) and penalties (the rejection). While the game makes you sweat here and there, the more you play, the more you build writing strategies and skills and hopefully, enjoy the game of writing.
The players in this game of writing for competitive work or education applications are you, your readers (who you want on your side) and your competitors (who you want to beat to the finish line.) Sometimes there are gatekeepers, those you must convince of your worthiness in order to be seen by the readers who have the ultimate power to decide your fate.
The rules of the writing game vary, depending on who is your reader and what is the prize. You must study your reader carefully to figure out what’s important to them before you begin to engage with them through writing.
As a skill-based game, writing is a tool that helps you learn about yourself. You have no idea what to say? Great! Write stuff down so that you can start to get a better idea. Keep writing and eventually you’ll find your voice.
During career transitions, you’ll be tested on what you know about who you are, what you value and what you yearn to do. When you take the time to learn about yourself through writing, you experience greater confidence in face-to-face situations, like a networking event or the interview. It’s also a lot more fun if you approach like a game!
Finally, making it a game helps you to put in context “you win some, you lose some.” It’s not personal when you don’t get the offer, but it sure is a terrific reward when you do.
Building skills to write about yourself eventually yields results that you want, such as admission to a top school or an offer to a job you covet. Remind yourself that if you approach it as a fun, creative exercise, it can be deliciously satisfying to get to the end of a well thought-out, well written piece that has your personal stamp on it.
2. Practice writing in low-risk contexts as preparation for writing in high-risk applications.

There are two kinds of writing you need to make time for if you are embarking on an education or work transition:
- Low-risk writing for your eyes, entertainment and education only
- High-risk writing that appeals to your audience and builds a bridge to your future
Engaging in both types of writing will improve the quality of your writing.
Low Risk Writing – for your eyes, entertainment and education only
Low risk writing is the pre-work, the primer for your final audience-focused documents. Writing in a journal, for example, is a terrific low-risk way to learn about yourself. It can help you clarify your working identity, sort through options and mentally try on possible futures.
Brainstorming on a piece of paper or using an electronic app is another great low-risk way to write your way to better understanding. Just try to brainstorm in phrases or sentences rather than single words only!
If you want to expand the audience circle beyond yourself, another low-risk writing context is social media. To maintain anonymity, create a secret identity to practice your writing (and get feedback) in a relatively low-risk context.
Your journalling, brainstorming and social media musings can include wildly ambitious goals and totally random, unrelated and unfinished thoughts. Doodles. Art work. Flights of fancy. Or they can follow thoughtful writing drills and exercises that deepen your craft. You be the judge.
High Risk Writing – appealing to decision makers in a way that builds a bridge to your future
On the other hand, writing resumes, cover letters and business proposals fall into the category of higher risk, higher stakes writing, as you have an audience at the other end. And your audience typically is a decision maker who has power to accept you or reject you.
Unlike writing about yourself in a private journal, writing high stakes self-introduction documents serves to develop relationships between you and others. In these documents, you are the subject of your writing, but are only one half of the writing/reading equation. Your documents become the bridge between you and your reader.
Therefore, in addition to writing about yourself, your writing needs first to understand your reader. It then must meet those needs by being focused, relevant, and informative.
Oh, and pretty much error free.
3. Use internal and external resources to improve your writing process

Whether low-risk or high risk, writing is a creative task. Therefore it’s helpful to think of it as a process of continuous improvement. It’s a ride, with right turns and wrong turns. With lows and highs.
To make the writing ride enjoyable and get to the other end, you need both inner and outer resources. So to wrap up, I offer two categories of resources to support your writing process: internal resources and external resources.
Internal resources, like clear thinking and noble character
Goethe was a German writer born in 1749. He translated the bible into German. So he knows a thing or two about writing. His words of wisdom remind us of two important inner resources for strong writing: clear thoughts and a noble spirit.
Each of these resources are worthy of an entire blog post – later! For now, keep these tips in mind:
- For clear thoughts. When you sit down to write, remember the importance of getting clear. Meditate for five minutes. Then remind yourself of your reader. Visualize him, her or them. Before you begin serious writing, create an outline to organize your thoughts and key messages. As you write, you don’t need to follow the outline. Just be mindful of it as a useful tool to organize your thoughts.
- For a noble spirit. If we define “noble” as “having or showing fine personal qualities or high moral principles and ideals,” there are many ways to apply this resource to the writing process. For example, aim for the personal quality of authenticity (= be real), the moral principle of honesty and the ideal of reciprocity in your relationship with your reader. Take your writing from all about “me” to more about “we.”
External resources like chocolate and web resources!
There are many external resources we need to keep us moving forward on our writing ride.
Like our mobile phone to recall our voice memos and notepad musings from earlier in the week. A pad of paper to transfer from our brain through our arm and hand our fleeting thoughts. And pencils to visualize our ideas in living colour. What would we do without our computer to organize and draft our scathingly brilliant ideas? How about some motivational quotes and soothing music to keep us marching towards our goal?
Finally, of course, chocolate. Who doesn’t need chocolate to fuel the writing journey?
The Internet also offers wonderful resources to support our writing tasks. In the table below are some of my favorites organized by:
- Education: tailor your resume or CV and personal statements for your education goals
- Job search: write cover letters, resumes and LinkedIn profiles to attract employer interest
- Small business: learn how to craft standard documents to build your small business such as proposal, business plans and reports
- Process, style & technique: access resources to improve your thinking, grammar, structure and accessibility
Curriculum Vitae (CVs)
- Purdue’s The Owl’s take on resume and CV writing
- University of Western Ontario resume, cover letter and CV samples
- CV writing advice from the Chronicle of Higher Education
Personal Statements & Letters of Admission
- University of Alberta’s Guide to Personal Statement writing, including samples
- Personal statement tips, videos and writing process app from the University of Toronto Scarborough’s Writing Centre & Academic Advising & Career Centre
- Studential.com – A UK perspective on the Personal Statement relevant to students in North America
Letters
- The Atlantic’s brief history of cover letters for those who want to know how and why the cover letter came to be important
- Cover letter writing resources from the University of Toronto Scarborough
- Monster’s take on Do’s and Don’ts for writing a cover letter
- The Atlantic offers some humour – how to write a cover letter, according to great artists
Resumes
- UTSC’s Resume-Building Tool – an online course in resume writing
- Resume Tweaks from the Muse
- Samples from Cardinal Expert Resumes
- Online course from LinkedIn on how to optimize your LinkedIn page
- The Muse’s 31 top tips to make your LinkedIn page stand out
Proposals
- Envato’s Guide to writing a winning business proposal – while there, download a template for a reasonable cost!
- The University of Michigan’s Proposal Writer’s Guide with section-by-section breakdown
- B2C’s Step-by-Step Guide for writing your first Request for Proposal (RFP) response
Business Plans
- Canada Business’ sample business plans for Canadian entrepreneur
- BDC’s template for creating a business plan
Business Reports
- Victoria University of Wellington (NZ) guide to writing a business report – includes process tips, structure and sample for the first time writer
Journaling
- Doorway to College’s journal prompts to find your niche for the career undecided
- Psych Central’s 30 journal prompts for self reflection and self discovery
- Kaizen Journaling on keeping a career journal and other journaling techniques
- Positive Psychology on writing therapy for personal growth
Style, Format, Grammar & Spelling
- Grammar Girl’s Quick & Dirty Tips to get your writing right
- The Owl – Purdue’s online writing lab with tips, techniques and style guides for all your writing needs
- University Writing Centre writing tipsheets for students
- Webaim on writing clearly and simply with Accessibility in mind
In Summary
Writing, like any creative undertaking, is a skill that requires ongoing practice to master for important education and work transitions. To improve your writing skills, turn your writing tasks into a game that makes it fun. Practice in low-risk and high-risk contexts. Play with writing for your eyes only to develop fluency and confidence. Get serious when writing high stakes applications so that you can produce quality materials worthy of a 2-thumbs up decision by your reader. Take advantage of the many resources out there to support your writing – both internal resources to fuel your motivation and focus, as well as external resources to tailor your writing to its intended audience need.