Tracking Your Progress When It Feels Really Hard

Hi there, welcome to Work Wise! My name’s Octavia Goredema.

I’m the CEO of Fire Memos, the author of Prep, Push, Pivot and the host of the Audible Original series How To Change Careers.

Every week I share insights and actionable steps to help you do your best work and achieve your career goals.

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When was the last time you started something new, and it was way harder than you expected?

Whether you’re settling into the first few weeks of a new job or transitioning into a new role, learning curves are inevitable but that doesn’t make the high-stress moments easier to experience.

Planning my book tour as a first-time author? At the outset I had no idea of how to gauge whether I was doing it right or doing it wrong.?

Creating the first financial models for my startup? I had to talk to so many founders to answer my array of questions before I could even begin.

When you’re doing something that matters for the first time it can feel like scaling a mountain. Last week I spoke to someone who is in the early phase of a challenging new role, and she said “frankly, it just doesn’t feel like I have any wins right now.”

When you start something new, there’s so much to absorb and as a result we tend to focus on everything you don’t know yet and what we haven’t mastered yet. But recognizing your learnings and progress along the way is key to staying motivated, especially during tougher times.

So today, I’ll walk you through practical ways to recognize your progress when you’re embarking on something brand new.

First Few Weeks in a New Job

In the first few weeks of a new job, everything can feel like a whirlwind. You’re learning about new processes, meeting new teammates, getting to know your manager, and trying to understand the culture. It’s easy to get lost in the chaos and feel like you haven’t achieved much. But there’s value in tracking even the smallest wins during this time.

?Tip: Create a daily wins list.

At the end of each workday, write down three things you’ve accomplished, no matter how minor they seem. Did you complete onboarding tasks? Great! Did you get introduced to a senior leader or ask your manager a clarifying question? Those are wins, too. These small accomplishments build up and every step at this stage matters.

Let’s say you’re in your third week at a new company, and you’ve finally managed to navigate their internal project management tool. It might not feel like much compared to the bigger tasks on your plate, but mastering the tool is a crucial win. Write it down and reflect on how what you know now, compared to day one.

Share your top three wins with your manager during your weekly check-ins. It shows progress and opens the door for feedback that can help you course-correct or build momentum.

Transitioning Into a New Role

Stepping into a new role, especially one with higher responsibilities, can make you feel like you need to prove yourself instantly. You might be comparing your current performance to where you were in your old role, which can lead to feeling inadequate. The truth is, transitions take time, and recognizing your progress is more important than chasing perfection.

Tip: Set smaller goals that will eventually scale.

Set specific, small goals for yourself in your new role. Instead of trying to master everything at once, focus on incremental achievements. Break down large tasks into manageable chunks and track your progress on each. For example, if your new role involves leading a team for the first time, your first win could be having a one-on-one meeting with each team member. Your next goal might be to set clear objectives for the team.

Last year I coached someone who had just been promoted to lead her team at a Series D technology company. She was now transitioning from an individual contributor role to a management position for the first time. In this instance, a win was making their weekly team meetings more productive.

It took a while to get there. My coaching client now had the responsibility of managing a small time of individuals who had been her peers, so she needed to find ways to set expectations. In the early days there were things that didn’t go perfectly, so I guided her to focus on what could be learned and to identify what was working.

Focus on Progress versus Perfection

If you’re adapting to a new role, focus on progress and learnings, versus perfection. Keep a progress journal where you document these incremental achievements.

Over at Fire Memos, you have the option to add wins and give them a personalized tag of your choice such as “Development” or “New Skills.” Over time, you’ll be able to see how much you’ve grown, even if it didn’t feel like much at the time.

Whether you’re in the first few weeks of a new job or transitioning into a new role, progress often feels small when we’re in the thick of it, but it adds up. Tracking your wins, no matter how small, allows you to see the bigger picture of your growth over time.

From mastering a difficult new tool in your first week to leading a contentious meeting in a new role, be sure to recognize the steps you’re taking along the way.

And based on my own experience, I also want to offer this one final piece of advice. Don’t wait for someone else to give you validation.

You are your own best advocate. By recognizing your wins, you build your own confidence and keep yourself motivated to keep learning and growing.

How do you recommend navigating challenging transitions? I read and respond to every single comment, so if you have an insight to share, or a question for me, let me know.

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