Starting something new always feels like standing at the edge of a cliff. You’re excited. You’re scared.

You don’t know if you’ll land or fall flat. When I first thought about launching an online business, I spent weeks just figuring out where to even begin.

It wasn’t the ideas that tripped me up. It was everything else – managing my time, learning new skills, and trying not to burn out.

The First 90 Days by Michael D. Watkins is a business and leadership book that teaches you how to survive and thrive during those critical early days of any new venture.

He breaks down what you need to do when stepping into a new role or building something from scratch.

Whether you’re starting a side hustle or still deciding what to build, this book gives you practical steps to move forward without feeling lost. If you’re tired of guessing, you’ll love what’s inside.

Detailed Summary of The First 90 Days by Michael D. Watkins

The First 90 Days by Michael D. Watkins is a leadership and business strategy book that shows you how to manage the chaos that comes with stepping into something new. He explains why the early days matter so much. If you mess up the first three months, it gets way harder to recover later.

He shares clear strategies to help you hit the ground running. You will learn how to mentally promote yourself into your new role. You will see why it is important to let go of what worked before and focus on what your current situation needs.

He teaches you how to build a focused learning agenda so you are not drowning in information. You get a plan to learn the right things at the right time. He also shows you how to match your strategy to your real situation, whether you are starting something new, fixing something broken, or taking something good and making it better.

Early wins matter. He breaks down how to find and create small wins that build your credibility fast. You will also learn how to negotiate successfully with the people above you so you are not left guessing what they want.

He pushes you to build your team, create strong coalitions, and stay steady through all the pressure. If you want to start your side hustle strong or finally take that online business idea seriously, this book can save you months of frustration and give you real momentum.

9 Lessons from The First 90 Days by Michael D. Watkins

Building anything new can feel overwhelming. You are juggling dreams, doubts, and deadlines all at once. Michael D. Watkins breaks down what you need to focus on first so you can stop guessing and start creating real momentum from day one.

1. Promote Yourself Mentally Before You Start

Michael D. Watkins says your first step is to mentally leave your old role behind. You are not the same person anymore. You cannot rely on what worked in your last job.

You have to picture yourself doing different things, thinking differently, acting differently.

Before you officially start anything, you should ask yourself:

• What new habits do I need to build?
• What old habits do I need to kill?
• How should my actions change in this new space?

Getting clear on this early gives you a clean break. You stop clinging to what feels safe. You open yourself to what is necessary.

2. Build a Learning Agenda

He explains that the faster you learn, the faster you succeed. But you cannot just “learn everything.” You need a smart plan.

You should define the most important things you need to know first:

• How does the organization work?
• What are the key goals?
• Who are the people who matter?

He suggests creating a learning timeline:

• What you must know before you start
• What you should figure out in your first week
• What you should master by the first month

When you set clear learning goals, you stop wasting energy. You move with purpose.

3. Match Your Strategy to Your Situation

Watkins warns that trying to apply the same plan everywhere is a trap. Different situations need different moves.

He outlines four types of situations:

• Startup: You are building from scratch.
• Turnaround: You are fixing something broken.
• Realignment: You are adjusting an existing operation.
• Sustaining Success: You are growing something that already works.

You have to ask yourself:

• Am I building, fixing, adjusting, or growing?
• How much time should I spend learning versus doing?

You do not want to waste time solving the wrong problem. Knowing where you are makes you more powerful.

4. Focus on Securing Early Wins

Watkins stresses that credibility is your currency. You need quick wins that prove you can get results.

But not just any win. The wins must:

• Be meaningful to your boss and the bigger mission
• Make a real difference in the eyes of your team
• Show you understand the culture

He also warns you not to just focus on “what” you achieve, but how you achieve it. If you win but burn bridges, you lose later.

Ask yourself:

• Where can I deliver real results fast?
• How can I win without stepping on people?

Early wins are not just about looking good. They set the foundation for your long-term success.

5. Negotiate Success With Your Boss

He explains that a lot of people fail because they guess what their boss expects.

You need to sit down and be clear:

• What do you expect from me?
• What can I expect from you?
• What does success look like in the next 90 days?

He even says you should agree on a “diagnosis period” before jumping into actions. That way you are not fixing problems you barely understand.

If you want to avoid last-minute panics and wrong assumptions, talk early, talk often, and talk clearly.

6. Achieve Alignment Early

Watkins says the higher you climb, the less your success depends on just you. Your success depends on how the organization fits together.

He explains that everything needs to be in sync:

• Strategy (what you are trying to do)
• Structure (how people are organized)
• Systems (how work gets done)
• Skills (what people are good at)
• Culture (how people behave)

You need to check:

• Are our goals clear?
• Does our setup help or block us?
• Do people have the skills to win?

If you skip this, you will push hard but still feel stuck. You cannot outrun bad structure.

7. Build Your Team Carefully

One of the hardest things Watkins talks about is team building.

You will feel pressure to keep everyone. You will feel guilty about moving people around. But you cannot build success without the right team.

He says to look at every team member and ask:

• Are they competent?
• Can they handle pressure?
• Do they have energy?
• Can they focus?
• Are they trusted?

You cannot afford to delay tough calls. Waiting too long to fix team problems will slow you down.

He also reminds you not to rush hiring just to feel less alone. It is better to go slow and hire right than to move fast and regret it.

8. Create Coalitions

Watkins shows that leadership is not about authority. It is about influence. Especially in new environments.

You will need people you do not manage to support you. He calls this “building coalitions.”

Start by mapping the people around you:

• Who can help you?
• Who might resist you?
• Who do you need to win over first?

He says do not try to win everyone at once. Focus on winning a few key allies. They will help you bring others in.

If you ignore coalition building, you will find yourself fighting solo battles you cannot win.

9. Keep Your Balance

Watkins closes by warning that burnout is real. The first 90 days are intense.

He says you must:

• Set clear boundaries
• Avoid overcommitting
• Stay connected to people who ground you
• Keep checking yourself for stress, tunnel vision, or burnout signs

You cannot pour from an empty cup. You need to plan your energy the same way you plan your strategy.

Ask yourself every week:

• Am I staying focused?
• Am I keeping my health in check?
• Am I asking for help when I need it?

Staying balanced is not weak. It is survival.

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The First 90 Days is packed with even more strategies, real-world examples, and detailed action steps. If you are serious about building your side hustle, leading a new project, or taking your online business idea seriously, I highly recommend grabbing the book.

Conclusion

Starting something new will always feel a little messy. The First 90 Days by Michael D. Watkins gives you a real plan to handle the chaos without losing yourself.

You do not have to figure everything out alone. If you want to build faster, lead smarter, or just feel less overwhelmed while chasing your business goals, this book can guide you through the noise.

And if you are curious about how to design products and habits people keep coming back to, you should check out my next post, where I share key lessons from Hooked by Nir Eyal.