Nils Rebehn

The first 100 days of freelancing feel like standing on the edge of freedom (and maybe panic). You’re finally your own boss, but suddenly everything depends on you. 

The next few months will make or break your business.

Most people don’t fail because they lack skill — they fail because they bring the wrong habits from employment into freelancing. 

I’ve made those mistakes myself, and I see them repeated every day.

What mistakes did you make in your own first 100 days?

I didn’t offer service packages soon enough. Every project I pitched for required a custom quote. I thought I was being flexible — tailoring every proposal to each client — but in reality, I was wasting hours reinventing the wheel.

Packages make you predictable. They save time, signal professionalism, and give clients clarity. The earlier you define what you sell, the faster you’ll start making consistent money.

Which mistakes do you see repeated most often in communities or forums?

The same five, over and over:

1. Pricing too low out of fear of rejection.
2. Overinvesting in branding (fancy logos, perfect websites) before testing the market.
3. Taking every client, even those with red flags, “for experience.”
4. Skipping systems like CRMs, time trackers, and invoicing tools.
5. And of course, confusing activity with progress.

Freelancing is a business, not a hobby. The earlier you treat it like one, the smoother your growth will be.

Why do new freelancers tend to undervalue themselves at the start?

Because freelancing strips away the psychological safety of a salary. When no one tells you what you’re worth, it’s tempting to charge whatever feels “safe.”

There’s also a myth that low prices make clients say yes faster. They don’t — they attract clients who don’t respect your time.

What most new freelancers forget is that they’re not just selling their skills. They’re taking on risk, taxes, administration, and accountability — things a regular employee never has to worry about. 

Those responsibilities deserve higher compensation, not less.

How can someone avoid being “busy but broke” in the early months?

Stop glorifying busyness. You’re not paid for effort; you’re paid for outcomes.

Focus only on revenue-driving work — anything that helps you find, serve, or retain clients. Everything else can wait.

Create a minimum viable offer — one thing you can sell easily and deliver well. Don’t build an empire; build momentum.

And start tracking your numbers from the very beginning. Know what you earn, how long things take, and which projects actually profit you. That data will become your compass.

If you could give one “do this, not that” rule for the first 100 days, what would it be?

Do this: Build one repeatable offer you can sell confidently. 

Don’t waste your first 100 days “building a business.”

Your primary task early on is to build your ability to attract and retain clients. 

Everything else — systems, branding, automation — comes later.

The freelancers who survive aren’t the busiest — they’re the ones who focus, price fairly, and think like business owners from day one.

Don’t Burn the Bridge: How to Leave Your Employer Professionally

Most freelancers think freedom starts with a resignation letter. It doesn’t. It begins with how you leave. Because if you walk out the wrong way, you’re not just quitting a job – you’re cutting off your first (and often easiest) client.

Leaving your employer professionally isn’t just about courtesy; it’s also about maintaining a positive reputation. It’s about strategy. It’s your opportunity to turn your past employer into your first paying customer, reference, or long-term ally.

What does it mean to “leave professionally” in the context of freelancing?

Leaving professionally means being transparent, respectful, and forward-thinking.

Discuss your plans openly with your manager. Don’t vanish behind vague excuses about “new opportunities.” Instead, make it clear that your decision isn’t about dissatisfaction — it’s about direction. You want to explore something the current path doesn’t allow.

Frame it as growth, not escape. When you position your transition as part of your personal development, most leaders respect that. They might even support it.

How can someone position their departure so their employer sees potential for collaboration instead of betrayal?

Start by removing emotion from the equation. Never speak negatively about colleagues, leadership, or company policies — not during the notice period, and not afterwards. Nothing kills trust faster than gossip.

Show that it’s not personal. If possible, highlight a limitation that freelancing can solve. It could be the flexibility your role couldn’t offer or the type of work that didn’t align with company priorities.

For example, I once faced rigid working hours that clashed with my preferred day structure. Instead of framing it as frustration, I positioned it as a logistical issue. With my new freelance flexibility, I’d be happy to stay in touch and support them on future projects. That turned a “goodbye” into an open door.

Do you have an example of an employee-turned-freelancer who kept their old company as a client?

Yes — myself. When I left my former employer, I made sure to keep good relationships across teams. They already knew my work ethic and trusted my expertise. So when they later needed extra hands for a project, I was often their first call.

Another smart move is to look into partner programs or official collaboration structures. Many companies offer them, and they serve as a perfect bridge from “employee” to “trusted ally.”

What are the biggest mistakes people make when resigning that hurt future opportunities?

The worst mistake is going silent. Too many people “exit quietly,” offering no explanation and disappearing overnight. That leaves confusion and kills potential future collaboration.

The second mistake is not to stay in touch. If your former colleagues don’t know what you’re doing now, they won’t think to reach out. Share updates, send a note, stay visible. LinkedIn is a good place to do this if you don’t want to send people direct messages. 

Because leaving a company doesn’t have to mean leaving relationships behind, handled well, your old employer can become your first customer or partner on the road ahead.

The Pros and Cons of a Gradual Transition into Freelancing.

Most people romanticise the “I quit my job and started my own business” story. But the truth is: leaping without a plan isn’t brave — it’s reckless. 

If you’re even thinking about freelancing, start by checking your employment contract. Never risk your job or compromise your employer’s trust. That’s not entrepreneurship — that’s self-sabotage.

What are the biggest advantages of side-hustling before going full-time freelance?

A side hustle is the safest testing ground you’ll ever have. You can experiment, fail quietly, and refine without betting your rent on the outcome.

First, it allows you to validate your service with minimal risk. You’ll quickly see what people actually pay for — not just what you think they will. 

Second, it allows you to build a financial cushion while you’re still earning a salary. A safety net doesn’t just protect your wallet; it protects your creativity. 

And third, it provides you with real feedback from real customers before you make a commitment. That data is worth more than any business plan.

When is it smarter to leap directly into self-employment?

Sometimes the timing is too good to wait. If your skills are in high demand and opportunities are already knocking, hesitation can cost you more than risk ever will.

It’s also smart to leap when you already have clients lined up or a company actively wants to work with you. That’s not a leap — it’s a transition.

I jumped when I knew my expertise was in demand, had savings for a few months, and a plan B if it didn’t work out. That’s what separates a strategic leap from a blind one.

What risks come with trying to juggle both a job and freelancing?

It’s hard. You’ll face conflicts of interest if your side work overlaps with your day job. Even if it doesn’t, you’ll struggle for time and energy.

The constant task switching between employee and entrepreneur modes can drain you faster than you expect. Many new freelancers underestimate that mental load.

So if you’re balancing both, treat your time and energy like a scarce resource (because it is).

Can you share a story of someone who successfully used each path?

I know someone who started offering marketing services while still employed. He used his job for stability and his free time for progress. Within months, he had clients, a refined offer, and the confidence to go full-time.

My path was different. I went all in — but not blindly. I knew demand existed, had savings, and was ready to return to employment if needed. That mindset turned risk into opportunity.

How should someone decide which route is right for them?

Start with the basics: are you even allowed to freelance? If your contract forbids it, that’s your answer.

If your employer allows it, test the waters first. A side hustle isn’t a sign of hesitation — it’s a sign of strategy. 

Once you’ve validated your service, proven you can earn, and learned how to manage yourself, then decide if the leap feels right.

The goal isn’t to be fearless. It’s to be prepared. Teaser for Socials

Testing the waters feels safe. Diving in feels bold. The trick? Knowing when to do which. Here’s my take for new freelancers.