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  • Why Founders Should Journal

    Being a founder is a rollercoaster. The highs are exhilarating, but the lows can feel overwhelming. A simple yet powerful tool can help you navigate this journey: journaling. It helps you gain clarity, process stress, and track your growth. Here’s why every founder should make it a habit.

    Benefits of journalling

    Writing is thinking

    As founders we’ll often have multiple issues and opportunities pinging around in our heads like a pinball machine. Unintentional rumination is not the way to process these thoughts properly and turn them into action.

    When we write, we think. We are forced to slow these thoughts down, consider them in detail, think of the practicalities and second-order effects—to take them seriously as ideas.

    The process of writing connects different areas of our brains, so we bring our creative and rational/executive functions online at the same time. It will move us beyond a daydream or anxious rumination, and lead us to a properly considered conclusion.

    This is shown to be especially true if we write by hand, but such an old school approach might be too much to ask for most fast-paced founder types, and there are benefits to a digital journal that we’ll come on to.

    This too shall pass

    However good or bad things seem to be at this moment, it’s probably not as good or bad as it seems, and this too shall pass.

    When choosing a journalling app, make sure you find one that supports ‘throwbacks’ (I recommend the Journey app).

    A throwback is an entry you made some milestone in the past (years or months ago).

    These are extremely powerful. They will remind you how far you’ve come. You’ll be reminded that this time three years ago you were suffering great anxiety about your cash position, but it too passed and you’re grateful to be in a more stable position now. When the next crises hits you’ll be reminded that you’ve been here before and that this one, too, shall pass.

    It may remind you that five years ago your product was evolving quickly, but now it’s become stagnant and is being threatened by competition. What’s changed? Have you lost energy? Has your culture changed? Have you made a bad hire?

    A simple reminder that three months ago you were absolutely loving the graft, but now your energy is dipping, might tell you it’s time for a break. Whatever that looks like to you (a day off walking in the hills alone, a week away with the family, indulging in a pet project), take the opportunity to re-energise.

    These data points on the arc of your journey will help you maintain perspective and recognise that your current situation is always temporary.

    Smell the roses

    Positive Affect Journalling (PAF – or simply ‘gratitude journalling’) is show to significantly reduce stress and anxiety.

    Throwbacks are a great source for gratitude, but it can be anything, however big or small, that reminds you that your life could be significantly worse.

    Examples

    • Family and friends.
    • Not having to catch a train to work every day.
    • A kind word someone offered you.
    • A positive behaviour that made you proud to be you.

    You don’t need to write an essay, but you should be specific. Don’t literally write “family and friends”, instead write something specific like “watching my son play football – it made me very proud to see how well he’s progressing in his game”.

    Intention setting

    At the beginning of the day or week, simply setting out your intentions will make it much more likely that you deliver against them. This isn’t a to-do list and you don’t need to go back to it and tick them off, instead you’re forcing yourself to think intentionally and vocalise your intentions to yourself.

    Examples: “today/this week I’m going to…”

    • “see if Doug is OK, he seems off his game.”
    • “get the accounts reviewed and filed, even though I’m dreading it.”
    • “take some time for myself by going for a long walk.”

    You’re negotiating and making commitments with yourself, which will make it much more likely that you’ll follow through.

    Top tips for journalling

    Don’t try too hard

    This is for you. No one is going to read it. In fact, you’ll probably want to password protect it—it’ll make you feel safer and more free to write honestly.

    Don’t try to be profound. Don’t proofread yourself. Just examine what’s on your mind and follow your thoughts.

    Make it a habit

    You’re not writing an essay each day (a 5-10 minutes will do it), but do try to be consistent.

    Stacking it on top of another habit is the best way to achieve this. For me, and at the risk of oversharing, it makes for perfect ‘me time’ during my morning dump.

    For you it might be something you do just after you get into bed, or when you put the kettle for an afternoon tea. Whatever it is, stack it on top of something you do at roughly the same time every day.

    Find root causes

    You may reflect that your energy is off, but try to examine why. How long has it been going on? Does it correlate with any changes in your circumstances? Are there any times of day you find particularly draining?

    You may surprise yourself to find that your week typically goes OK until Wednesday evening, because you know you have that 121 with Malcolm in the morning. You may reflect how often you make up an excuse and cancel on Malcolm. This is signal that you should pay attention to.

    Think about all of your life

    Try not to make this a purely professional journal. There’s a huge overlap between all aspects of your life, and this is your chance to unify your thoughts.

    You might reflect that those issues you’ve been having with your partner are caused by the stresses in the office. You may realise that your kids bring their own flavour of stress to your day, but overall they’re a huge tonic to you. You might correlate greater creativity in the office with your new sleep routine.

    Look for gaps

    If you really don’t have much to say in your journal other than work-related stuff, this is a gap. Find a hobby, however small. Learn something new that’s unrelated to your work. Pick up the guitar that’s covered in dust and brush up on your chords. Get back into Duolingo. Organise a curry with the lads. Whatever it is, your journal is a barometer for how balanced your life is.

    Start now

    And most importantly, just start. Find an app (or even a Google Doc will do – but I do recommend Journey for the Throwbacks), and begin. How do you feel? Why do you feel that way? What can you do to be more the person you’d like to be? What are you grateful for?

    Journaling is one of the easiest yet most impactful habits a founder can adopt. It helps you stay grounded, make better decisions, and appreciate the journey. So don’t overthink it—just start writing.

  • Founders: you probably need to be more obsessive.

    You probably don’t often get accused of not being obsessive enough. You’ve been obsessive enough about your product to build a business around it. But here’s the real question: are you equally obsessive about the business itself—or business in general?

    Your vision drove you to create your business. You identified a problem that only your product could solve. You knew it wouldn’t be easy, and that it would take years of hard work before your vision would change the world.

    But your product doesn’t exist in isolation. Your product grows within your business. Your business provides the resources it needs to develop. If your business isn’t healthy, your product won’t make it.

    You need to be as obsessive about your business as you are about your product.

    Become ‘expert enough’ in all core functions

    Your passion for your product is unquestionable, but what about the areas outside your comfort zone? Maybe you find finance tedious, think marketing is just fluff, or consider HR a maze of red tape. If so, it’s time to change your mindset.

    If you have a growth mindset—as you should, it’s an essential trait of a good founder—then you’ll recognise that you reject these disciplines because they’re outside of your comfort zone.

    Run into the fire. You don’t need to get a batchelors degree in any of these core disciplines, but you should at least read the ‘For Dummys’ books. You should ask trusted friends to talk you through the basics. You should search Youtube for “how to prepare a cashflow statement”. Ask ChatGPT some questions to help you learn.

    As a starter:

    Sales & Marketing

    • Learn the basics of digital marketing (SEO, paid search, social media, and email marketing).
    • Understand the fundamentals of branding (differentiation, aspiration, and positioning).
    • Figure out how to create a sales funnel.

    Human Resources (HR)

    • Familiarize yourself with employee onboarding requirements (e.g., right-to-work checks).
    • Learn the basics of managing performance and navigating terminations.
    • Study effective management principles.

    Finance

    • Understand the difference between a P&L, cash flow statement, and balance sheet.
    • Learn the basics of business valuation.
    • Get comfortable with terms like accruals, provisions, and CAPEX.

    Legal

    • Research the regulations that apply to your industry and market.
    • If selling internationally, understand compliance requirements for those regions.

    Technology

    • Explore the most popular programming languages and their use cases.
    • Learn basic SQL—it’s easier than you think.
    • Identify the right platforms and tools for your business.

    Operations

    • Study the principles of Lean Six Sigma.
    • Know the top health and safety requirements in your operational areas.

    Why it matters

    You’ll make better hires

    Early hires are critical. A poor hire in finance, marketing, or HR can significantly impact your business. Understanding the basics ensures that you can evaluate candidates effectively and hire with confidence.

    You’ll be a better manager

    Even if you hire experts, you need to know enough to assess their performance. Without a foundation, how will you know if they’re delivering or missing the mark? Understanding the basics lets you ask the right questions and trust your instincts.

    You’ll see new opportunities

    Learning about business practices from companies like Apple or Amazon can spark ideas. For example:

    • Apple’s cash flow management might inspire you to improve your financial planning.
    • Understanding how Slack started as a side project could open your mind to pivots or diversification.

    You’ll be prepared for exit

    At some point, you may want to sell your business. Understanding valuation principles and investor expectations now can save you headaches later. Watch videos like Aswath Damodaran’s series on business valuation to get started.

    Embrace the process

    Learning doesn’t have to be daunting. Podcasts like PivotFounders, or Business Breakdowns can make your commute insightful. You’ll gain confidence in your ability to discuss HR, finance, or marketing. Over time, you’ll start to enjoy connecting the dots between disciplines.

    Start today

    Invest an hour a week into learning something new about business. Pick up a book, subscribe to a podcast, or watch a tutorial. Your growing expertise will benefit your business—and your product.

    Obsess about your business, not just your product. Your product will thank you for it.

  • Taking Back the Master Bedroom: A Founder’s Guide to Leading Your Business

    Taking Back the Master Bedroom: A Founder’s Guide to Leading Your Business

    As your business grows, do you ever feel like a guest in your own house? Imposter syndrome, fear of micromanaging, and distance from day-to-day details—it’s a common struggle for founders.

    Remember, this is YOUR house.

    A founder is not a typical CEO. You risked everything to back yourself. A significant part of your net worth is tied up in the business you created. You sacrificed a lot to build this house.

    Bringing in great people to handle details is the right move, but they are guests in YOUR house. Welcome them, pride yourself on being an excellent host, but don’t let yourself be pushed aside.

    You’re a generous host, offering drinks, meals, and a place to stay—but the master bedroom is yours. Nowhere is off-limits to you. Guests don’t get to bring others without your approval or argue when you ask them to leave. If they can’t respect your house rules, they might not be the right fit.

    You might offer the master bedroom or adjust your behaviour to make guests comfortable, but it’s your choice. If you want to check on someone in marketing, ask them directly. You might go through the manager out of respect, but you’re not obligated to. If you want to visit the warehouse or question a team member’s fit, act on it.

    No one likes being called a micromanager, but that’s a different issue. A micromanager skips context, bypasses leaders, and issues abrupt orders. A good founder stays connected, explains the ‘why,’ and empowers the team while guiding decisions.

    You might avoid the corner office or prime parking spot to feel like “one of the team.” That’s understandable, but you are different. You’re the host. Own it. Don’t deny yourself privileges you’ve earned—it’s like being embarrassed to sleep in the master bedroom when you have guests.

    You might insist your team tracks leave in the HR system while you don’t. You might walk in at 10 and leave at 4, but they don’t see the weekends you worked or sacrifices you’ve made to get here.

    The exception is your company’s values. These must align with your own. If you can’t live them, you’ve chosen the wrong values.

    You don’t need to justify this host/guest differentiation. As a founder, you’re likely the hardest-working, most stressed person in the business. You’ll ensure payroll is met during tight cashflow while maxing out your credit cards to keep the business afloat.

    Your role as a founder is unique. Own your space, lead with clarity, and don’t shy away from the privileges you’ve earned. Stay true to yourself and your values, and you’ll inspire the right people to thrive alongside you in YOUR house.