I’ll never forget the moment I realized my inability to take initiative was suffocating my career.
I was sitting in my boss’s office at a marketing agency, pitching an idea for the third time that week. I wanted to restructure our content team—a change I knew would be more efficient and better for our clients. As the Director of Content, it should have been my decision to make. But I still had to ask for permission.
The answer was the same careful consideration I’d heard before, followed by a polite “Let me think about it” that really meant “No, but I don’t want to discourage you completely.”
I kept coming back with the same pitch, certain that if I just explained it better, they’d see the value. They never did.
This became the pattern. Every idea needed approval. Every experiment required sign-off. Every deviation from “how we’ve always done it” needed to go through channels.
I was good at my job. I had ideas that could work. But I’d become so trained to ask for permission that I’d lost the ability to just do things.
After months of this, I made a decision that felt terrifying at the time: I quit and started freelancing.
Seven years later, I’m still going strong as a solopreneur. Not because I’m smarter or more talented than I was back then, but because I learned something crucial: taking initiative and practicing self-direction make the difference between a career that happens to you and one you actually control.
What taking initiative actually means
Taking initiative means making decisions and taking action without waiting for explicit permission or direction. It means identifying problems, proposing solutions, and moving forward even when no one told you to.
Self-direction vs. recklessness
There’s an important distinction here. Initiative doesn’t mean being reckless or ignoring the people around you. It doesn’t mean bulldozing through without considering consequences or feedback.
Recklessness is acting without thought. Self-direction is acting with purpose.
When I started freelancing, I didn’t just throw spaghetti at the wall, hoping something stuck. I assessed what I was good at, identified gaps in the market, and made calculated moves based on what I knew. I gathered information, sought advice from people who’d done it before, and then made my own decisions.
The difference comes down to preparation and awareness. Reckless people ignore risks. Self-directed people acknowledge risks and decide to move forward anyway.
Related: Taking risks is scary. Avoiding risk is worse.
What skills you need to take initiative
Taking initiative requires a specific set of skills that most people can develop with practice.
Self-awareness. You need to understand your skills, your limitations, and the context you’re operating in. This means honestly assessing what you’re capable of and what you still need to learn.
For more advice on building self-awareness, check out these articles:
Confidence. Not the loud, performative kind. It’s the quiet confidence that comes from trusting your judgment enough to act on it. It’s believing that even if you make a mistake, you’ll figure out how to fix it or learn from it.
Here are more articles that can help you develop confidence:
Decision-making ability. The freelancers and entrepreneurs who succeed aren’t the ones who make perfect decisions every time. They’re the ones who make decisions, period. They gather information, weigh their options, and then move forward instead of staying stuck in analysis paralysis.
We have a lot of content here about making tough decisions easier:
Accountability. When you take initiative, you own the results—good or bad. This means being willing to stand behind your decisions and learn from the outcomes. Here’s our full guide to accountability and taking responsibility for your actions.
Why taking initiative feels so hard
Most people know they should take more initiative. They recognize the value of self-direction. But when the moment comes to actually step up and make a decision, something holds them back.
That hesitation comes from deeply ingrained patterns—some formed in childhood, others reinforced throughout school and early career experiences. For me, learning what these barriers were and how to counteract them helped were essential steps in my path toward taking initiative.
Related: Trying Something New: Why It’s So Scary and Why It’s So Worth It
Here are a few of the most common thoughts that plagued me when I was first getting the hang of self-direction, and how I counter them.
“I’m afraid people will be upset with me”
This was the big one for me. I still worry sometimes that making a decision without asking will offend my clients. Back when I was working full-time, I was scared taking initiative would annoy my colleagues or create conflict.
The problem with this thinking is that you’re giving other people’s potential reactions more weight than your own judgment. You’re also assuming that people will be upset, when in reality, most professionals respect initiative when it’s executed thoughtfully.
Related: Thinking Traps: Rewire the Thoughts Holding You Back
When I started freelancing, I stopped asking clients if I could try new approaches. I’d say “I’m planning to restructure this content strategy to improve results” instead of “Would it be okay if maybe we could possibly consider…?” The clients who wanted a strategic partner appreciated the confidence. The ones who wanted someone to just follow orders weren’t the right fit anyway.
“What if I fail?”
Fear of failure keeps more people stuck than almost anything else, and I’m no stranger to this one either. You imagine the worst-case scenario: your idea bombs, everyone sees you mess up, and your reputation takes a hit. This is known as catastrophizing, and I’ve seen it tank more than one freelancer or solopreneur before they even got started.
In reality, small failures while taking initiative rarely matter as much as you think. Most decisions are reversible. Most mistakes are fixable. And the people who never fail are usually the ones who never try anything new.
The bigger risk is spending years waiting for permission and watching opportunities pass you by. I’ve failed at plenty of things since starting my business—pitches that went nowhere, strategies that flopped, clients I couldn’t help. None of those failures defined my career. The initiative to keep trying did.
“I don’t have enough experience yet”
This is impostor syndrome dressed up as humility. You tell yourself you need more training, more credentials, more years under your belt before you’re qualified to make decisions.
The truth is, waiting for perfect readiness is just another form of asking for permission. You’re waiting for someone else—a boss, a degree program, an arbitrary timeline—to tell you that you’re ready.
Experience comes from doing, not from waiting. When I quit my job to freelance, I had seven years of marketing experience, but zero years of running a business. I learned by taking initiative and figuring it out as I went. If I’d waited until I felt completely ready, I’d still be in that office asking permission to restructure the content team.
“Someone else should probably handle this”
This thought pattern stems from years of institutional training. In school, you raised your hand and waited to be called on. At work, you stayed in your lane and let the “experts” or higher-ups make the calls.
But defaulting to “someone else” means you’re constantly giving away your power. You’re assuming that other people are more qualified, more capable, or more deserving of making decisions than you are.
Sometimes that’s true. But more often, the person who should handle it is the person who sees the problem and has an idea for solving it. That might be you.
What happens when you start taking initiative
The shift from waiting for permission to taking action creates a ripple effect across your entire career. Some changes happen immediately, others build over time. But once you start practicing self-direction, the benefits compound in ways you can’t predict from the sidelines.
You learn faster through real decisions
Reading about marketing strategy is useful. But I didn’t really “get it” until I started doing the hands-on work—restructuring a client’s content plan and seeing what works taught me ten times more in half the time.
When you take initiative, you’re forced to experiment and test your ideas in the real world. You can’t hide behind theory or best practices—you have to make actual decisions and live with the results. This creates immediate feedback loops that accelerate your learning.
Creativity flourishes in this environment too. When you’re constantly asking permission, you’re limited to ideas that seem safe enough to get approved. When you’re directing yourself, you can try unconventional approaches, test weird hypotheses, and explore solutions that might sound ridiculous in a pitch meeting but actually work in practice.
Some experiments will fail. That’s the point. Each failure teaches you something specific about what doesn’t work, which is far more valuable than vague assumptions about what might work if someone let you try it.
You build confidence through action
Confidence doesn’t come from affirmations or positive thinking (though those things can help. True confidence comes from doing hard things and realizing you can handle them.
Every time you take initiative and survive the outcome—whether it succeeds or fails—you prove to yourself that you’re capable of making decisions. You build a track record of trusting your gut and dealing with consequences.
This confidence is visible to others. Clients, employers, and colleagues can sense the difference between someone who needs constant validation and someone who can assess a situation and act on it.
You become more valuable
People who take initiative are rare enough to be valuable. Most workers do exactly what they’re told. Some do it well. But the ones who identify problems, propose solutions, and execute without needing their hand held become indispensable.
As a freelancer, this became obvious fast. Clients didn’t just want someone to execute tasks. They wanted someone who could look at their business, spot opportunities, and take action. The more initiative I showed, the more they trusted me with bigger projects and better rates.
The same applies in traditional employment. Employees who wait for detailed instructions are replaceable. Employees who take ownership of outcomes become the ones companies fight to keep.
You attract opportunities instead of waiting for them
When you consistently take initiative, opportunities start finding you instead of the other way around.
People notice when you make things happen. They remember the person who launched that project, pitched that idea, or solved that problem. They start thinking of you when new opportunities come up.
Most of my best freelance clients came from referrals. Someone saw me take initiative on a project, remembered it months later, and recommended me to a colleague. I didn’t have to chase those opportunities—they came to me because I’d built a reputation for getting things done.
Freedom looks good on you.
Learn how to lead yourself, build real-world autonomy, and create the kind of freedom most people wait years to earn.
Practical ways to take initiative and develop self-direction
Building the habit of taking initiative doesn’t require a dramatic gesture. You don’t need to quit your job or launch a business tomorrow. Start with manageable steps that build your confidence and prove to yourself that you can make decisions.
Here are some suggestions on how to start building your self-direction muscle.
Start small with low-stakes projects
Pick something where the consequences of failure are minimal. Maybe it’s a personal project—reorganizing your home office, starting a side hustle, or learning a new skill without taking a formal class.
At work, look for small opportunities to take ownership. Volunteer to improve a process that’s been bugging you. Propose a minor change to how your team handles something. Take on a task that nobody else wants to touch.
Don’t worry about success or failure (at least, try not to let it catch you up). The goal is to practice making decisions and following through without asking for permission at every step.
Learn to pitch ideas instead of asking yes/no questions
This was a major shift for me when I started freelancing. Instead of asking “Can I try this approach?” I started saying “Here’s what I’m planning to do and why I think it will work.”
The difference is subtle but powerful. When you ask a yes/no question, you’re giving someone else control over your decision. When you pitch an idea, you’re demonstrating that you’ve already thought it through and you’re prepared to act on it.
This works in traditional employment too. Instead of “Should we change our content strategy?” try “I’ve identified three problems with our current approach and here’s a strategy that addresses them.”
You’re still communicating with stakeholders. You’re still open to feedback. But you’re positioning yourself as someone who makes decisions rather than someone who waits to be told what to do.
Build skills that give you leverage
The more valuable your skills, the more freedom you have to take initiative. When you’re highly capable, people trust your judgment more readily.
This doesn’t mean you need to master everything. Pick a few areas where you want to develop real expertise. Then pursue that knowledge aggressively—through practice, learning from others, and deliberate experimentation.
For me, it was SEO and content strategy. Once I became genuinely good at those things, clients stopped micromanaging my decisions. They hired me because they trusted I knew what I was doing.
Here are some resources we have on developing skills on your own:
Find mentors who model initiative
Working with people who already practice self-direction shows you what it looks like in action. You see how they handle uncertainty, how they make decisions without perfect information, and how they recover when things don’t go as planned.
Look for mentors who took risks in their careers, who built something from scratch, or who regularly challenge the status quo. Avoid people who only succeeded by following the prescribed path—they won’t be able to teach you how to forge your own.
Don’t worry if it takes time for you to develop the confidence and courage required to take initiative. If you’ve made it this far in the article, then you’re already on your way. Start slow, and build up to things that have more and more weight. Eventually, you’ll stop sweating when it comes to self-direction, and you’ll have the ability to take initiative and push your career forward.
