My Blogging Journey (mistakes, checkpoints + monetizing)

This post is a story — a record of my blogging journey so far. It’s full of all my setbacks, learning moments and current plans.

This post is full of information I wish I had when starting out.

So consider this both a cheat sheet and a map – a cheat sheet to avoid the mistakes I made and a map to reaching realistic goals and monetizing your blog.

This is part 6 of my 6-part blog mastery series.

Let’s get to it.

Table of Contents Show


    Hey there, just a heads up that some of the links in this post may be affiliate links. That means I earn a small commission. This is at no extra cost to you, but helps me keep the lights on. Thank you for your support!


    Lessons Learned (8 mistakes I made)

    Let’s kick things off with my top blogging mistakes.

    These are the missteps that slowed my progress — but they were key learning moments for me.

    Hopefully you can speed things along by avoiding a few of them.

    1. Rushing to Make Money

    My first blog had one goal: to make money and make it quick.

    This was my biggest mistake.

    There’s nothing wrong with making money from your hard work (of course) but rushing into it too early rarely works. And if it does, it’s not sustainable.

    Making money is nuanced and has a lot of moving parts. But one truth is this: it requires trust, strategy and a lot of upfront value.

    So my core focus now is to always be adding value. This is my first and last priority.

    2. Going Too Broad

    My first blog was way too broad.

    My focus was digital marketing and Facebook ads for small businesses. This is a very competitive niche and I didn’t have any unique experience in the industry.

    If I could go back, I’d do this:

    • First, choose a specific niche (for example Facebook ads for spas)

    • Next, find clients and get them real results

    • Then, share my strategies as content for free

    This would have been a great approach. But I was new, so I can’t be too hard on myself.

    Also, starting broad is sometimes necessary. It can help you discover what your true niche is through writing and experimentation.

    3. Not Writing for My Audience

    As I just mentioned, I never had a narrow audience avatar — there was no specific person I was writing for.

    I was blogging for everyone, and by default, I was blogging for no one.

    Nowadays, this is a crucial part of my blogging process.

    I think about exactly who my audience is and why they’re reading my articles. I go above and beyond to solve their problems and their pain points.

    It seems like an obvious thing to consider, but it’s often overlooked.

    So now I research my audience, create reader personas and gather feedback whenever possible.

    4. Not Making My Content Stand Out

    My first blog had no differentiation.

    I wasn’t writing from personal experience or any expertise. I was just regurgitating what other people in my space were also probably regurgitating.

    I was a dull needle in a very big haystack. And that was adding zero value to the market.

    So now, I leverage my differentiation.

    For example, I am my audience. I write for other creative people and fellow starstruck dreamers.

    I leverage my life as a tech-curious musician who travels and struggles with imposter syndrome to share my adventures in creativity, blogging and creative entrepreneurship.

    Almost everything you read in this blog is exactly what I'm doing in my own life, in real time.

    5. No Planning

    If you haven’t guessed already, my first blog had no planning.

    My keyword strategy was misguided, my posting calendar was mood-based and my content planning was nonexistent.

    I didn’t have clear goals or a purpose (besides just making money). So my blog and its content reflected this aimlessness.

    Still, it was a fantastic learning experience for me.

    So if you’re struggling with this issue too, that’s okay — it’s totally normal.

    Just keep at it and push through to the other side (it does get better — way better).

    6. Too Many Affiliate Programs

    Since I was rushing to make money way too quickly, I ended up promoting everything and anything.

    I signed up for every affiliate program that was even remotely related to digital marketing and running an online business.

    10+ website building platforms, social media schedulers, quiz-makers…

    You name, I had an affiliate link for it.

    Of course, I never tested the majority of these for myself. I just studied the websites and transcribed the features into my own words.

    I recommended everything.

    I sold nothing.

    I mean, even I was confused about what the best option was (I can only imagine how my poor readers felt…as few as they were).

    7. Too Much Fluff

    This is more of a writing tip, but learning how to cut the fluff is an essential skill for blogging.

    My first articles over-explained topics and included discussions that added no real additional value.

    I suppose this is what growing as a writer looks like though…

    Still, I should have done more proofreading and I could’ve studied more about how to write a great blog.

    So my advice? Learn how to cut the fluff — the sooner, the better.

    8. Rogue Expectations

    My expectations for my first blog were unreasonable.

    Even worse, they weren’t specific or strategic.

    I saw my timeline like this: start a blog, create some content, throw in some affiliate links, make money.

    I mean, that’s kind of how it works — but there are key pieces of the puzzle missing.

    I lacked patience, wasn’t process-oriented, had unrealistic expectations and wasn’t thinking in the long-term.

    So my advice? Don’t think about how you can make money in the next 3 months.

    Think about where you’ll be in 1, 2, 3+ years if you consistently add value, get better and post regularly.

    Cultivate a successful blogging mindset.

    4 Key Checkpoints (my blog growth timeline)

    The checkpoints below follow my blogging journey (for this site).

    It’s a timeline you can use to guesstimate your own path.

    But everyone’s different (and timelines vary), so think of these as just some general benchmarks to work towards and expect.

    Checkpoint 1 (honeymooning)

    This is a fun checkpoint.

    At this stage, you’re still new and figuring out your content angles and strategy.

    I did a lot of research and testing in this first phase. I was still dialing in my niche, so my content was hopping around a bit.

    But it’s always fun starting something new (at least for me). There’s a lot of design decisions, topic exploration and content planning.

    And I love nerding out on that stuff.

    My Timeline for Getting Things Going:

    1-2 months

    Checkpoint 2 (the first 50)

    Reaching your first 50 posts already sets you apart from the majority.

    It’s an amazing feat, and something to be extremely proud of.

    A lot of people will even start to get good traffic numbers at this point (if the keyword research and SEO are really dialed in, that is).

    But reaching this milestone is all about keeping your head down and just writing.

    Yep — write, publish and repeat, that’s the method here.

    My Timeline to Reaching 50 Posts:

    Around month 3 to 4

    Checkpoint 3 (halfway slumps…)

    Reaching 50 blog posts is awesome, but nothing really happened.

    I wasn’t making money and my traffic wasn’t amazing (I also didn’t dial in on my niche until later).

    And doing something without any return for an extended amount of time is hard.

    You’re going to hit a wall (a few of them to be precise).

    This is your halfway slump and it’s completely normal (I still hit them).

    So we need a solution to get past this third checkpoint — we need a system.

    For me, this means using a blogging workflow and building habits through discipline and consistency.

    Motivation is fleeting. But discipline is a skill that will take you further than anything else.

    My Timeline for Building A System:

    Months 5-6

    Checkpoint 4 (money stuff)

    In the beginning, I wasn’t too concerned with monetizing. I focused on output (i.e. writing awesome content).

    But eventually, pulling some monetization levers started to make sense.

    This is exciting.

    So how do you know when it’s time to monetize?

    This will vary for each person, but here are some tips:

    • Wait until you start getting decent traffic numbers (especially for ad placements)

    • Wait until you know exactly who your audience is and the products they’d benefit from

    • Wait until you test products so you can show specifically how it will benefit your audience

    My Timeline for First Monetization:

    Around month 10

    Blog Monetization (7 ways to make money)

    Graphic from Canva. Grab a free account here.

    When you are ready to start making money, these are the top methods commonly used.

    They’re pretty standard strategies and other blogs will likely echo these ideas.

    But just be sure to choose ones that make the most sense for your goals, traffic, audience and niche.

    1. Sponsored Posts or Paid Product Placements

    This was the first way I monetized my blog.

    I got paid to include a product recommendation within one of my posts that performs well in Google.

    This is a common way for blogs to make money.

    Companies and brands will pay you to either create new sponsored content on your blog or for a product placement within one of your existing posts.

    You’ll just need to first have verifiable traffic and/or an audience.

    Some brands will reach out to you directly, but you can also do the cold outreach yourself to find these opportunities.

    Learn more here.

    2. Affiliate Marketing

    Affiliate marketing is another super common way to monetize a blog.

    This is where you partner with businesses and promote their products within your content. You’ll get a percentage of any sales you refer.

    These referrals are a great way to make passive income from a blog.

    For example, if you’re keen to start a blog (but don’t want to learn the ins and outs of WordPress), I always recommend Squarespace, which is what I use.

    That Squarespace link is an affiliate link, meaning if you click on it and build a website with them, I’ll get a cut of that sale — in which case, many thanks!

    (note: there is no additional cost for using my affiliate links)

    Learn more here.

    3. Ads

    Ad placement is a super common way to monetize a blog.

    The biggest caveat here is you’ll need good traffic numbers to make anything meaningful.

    Google Ads is a popular place to start, but there are higher-paying ad networks.

    Mediavine or Ezoic are two popular options (but Mediavine requires that your blog has at least 50,000 monthly visits).

    Learn more here.

    4. Selling Your Services

    If you have a service you can offer, a blog is a great lead generation machine.

    For example, I offer my SEO and blogging services within some of my (relevant) content and pages.

    This is an active form of monetization however (meaning you need to trade your time for money).

    A common goal for many bloggers is to have more passive streams of income. But offering services is a great way to start making money quicker.

    Because higher traffic numbers are generally required to make substantial money from things like affiliate links and ad placements.

    Learn more here.

    5. Selling Products

    Selling products is an awesome revenue stream for a blog.

    These can be either physical products or digital products.

    Digital products are popular for their passiveness (make it once, sell it forever). But physical products can be passive too (if you opt for a dropshipping strategy).

    Whatever the case, just be sure your products match your content, audience and brand.

    That is, don’t just sell stuff for the sake of selling and making money.

    Learn more here.

    6. Premium Content or Memberships

    Once you have an audience and some authority established, premium content can be a solid monetization strategy.

    For example, adding a paywall or a membership requirement in order to access exclusive content.

    A lot of blogging platforms will have membership capabilities as part of their features (or you can integrate a third-party app).

    But just remember to have the timing right on this and be sure that the content is indeed exclusive.

    Learn more here.

    7. Tips + Donations

    One last way to monetize your blog is through tips and donations.

    For example, you can add a Buy Me a Coffee button to your website and allow visitors to give you a tip for your content (you can also do memberships with them).

    Tips and donations may sound a solid low-stress way to start making money with your blog, but you’ll probably need a lot of traffic (or a very passionate audience) to make a meaningful amount.

    Learn more here.


    Want More? Check Out These Sweet Reads!

    Jef Quin

    Hey. I’m Jef — a digital nomad and the sole content creator for this site.

    I’m a traveler, musician/producer, blogger, content strategist and digital creator. And I’m on a mission to inspire a more chill, adventurous and creative lifestyle.

    I also spend a lot of time in Japan and love coffee.

    Drop me an email to say what’s up!

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