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Invest in yourself with continuing education

After we waded through way too many dot gov links to learn about healthcare in the last step, you can look forward to a more fun and exciting section. Here, we’re going to figure out how you can continue to grow as a freelancer.

You are your own boss, and you can give yourself a promotion

At a W-2 job, your employer will often sponsor education, courses, certifications, and additional ways for you to keep growing as an employee. You should do the same for yourself as a freelancer.

If you want to continue gaining new skills and accelerating your career – or even having the freedom to change the trajectory – it’s important to upskill. In a W-2, you’ll be regularly promoted and given raises. As a freelancer, you’re in charge of your professional advancement.‍

Upskilling lets you charge higher prices. It allows you to give yourself a promotion. And worse, if you don’t actively educate and upskill yourself, you risk falling behind. Staying ahead of the curve allows you to be even more valuable to clients as time goes on and gives you grounds to give yourself a promotion by raising your rates. You need to inherently value the work you do for your clients more as time goes on. 

A couple of ways you can do this as you upskill yourself:‍

  • Raise your rates at the end of the year

  • Every time you get a new client, ask for 5% more

  • Look for fellowships that pay you to learn skills. 

To get there, you’ll want to self-identify the areas for improvement and upskill accordingly. For example, I knew I wanted to improve my business coaching and grow my public speaking. I invested in coaching to improve my skills in those areas. Then, when I wanted to break into podcasting, I took courses to learn what I needed.‍

Make your plan to get that promotion

There are so many different ways to upskill yourself. Here are a few examples I recommend:

  • Coaching. This 1:1 development can give you skills and accountability to improve. It’s a big investment, but it’s a great way to kickstart your learning. You may have to try multiple coaches before you find the right one, just like finding the right therapist.

  • Online courses. Platforms like Upskill and Udemy offer a selection of courses. You can do these on your own time. Of course, I recommend Pollen!

  • Conferences. Don’t let businesses have all the fun – look for noteworthy conferences in your area and go network. 

  • Certifications. If you want to post proof of your learning, you can get certified in pretty much any skill. I recommend LinkedIn, EdX, and Coursera to find and get certificates on your skills.

  • Webinars. These may be paid or free.

Tip: Short on money? There’s almost always someone who will pay you to learn. For example, I got a job producing a podcast. Had I ever in my life cut tape? No. But I was interested in the field, so I applied and got the job. Now I’m getting paid to learn a skill that will make me a more valuable freelancer.

Don’t do these ad-hoc. Identify skills you’re weak in or skills that would allow you to charge more, like thought leadership writing, or skills that would allow you to expand your business, like public speaking. Plan to spend a certain amount per year on investing in those skills. 

I recommend setting aside a percentage of your annual income for these upskilling opportunities. I set aside 3% of my income every year. Start small, like 0.5%, and grow from there as your income grows. 

And remember, those expenses are tax deductible! As long as you can legally qualify those expenses as business-related, you can claim them as a tax deduction. 

Tip: What’s tax deductible? If I attend a workshop on public speaking, that’s tax deductible. If I attend a conference showing cat breeds, that is (sadly) unrelated to my work and not tax deductible. 

If you want more guidance, I highly recommend Turbo Tax’s resource on the top tax write-offs for self-employed people. 

Build your continuing education package 

Ready to get educated? Here’s an exercise from your workbook to point you in the right direction:

  • What skill do you want to improve to charge higher prices?  _____________

  • What skills do you want to gain to grow your business in a new direction? ___________

  • What weakness do you want to mitigate to avoid being outcompeted? ___________

For example, imagine Sara is a copywriter with one year of experience. Sara might want to get a certificate in persuasive web page copy to charge higher prices. She might want to learn about personal essays to add a new branch to her business. And she might need to learn about content marketing to avoid being outcompeted by her competitors. 

A few options for you to consider:

  • Do you want to take a class on writing SEO? 

  • Are you interested in building your tax knowledge through webinars? 

  • Do you want to network with other freelancers in your niche? 

  • Are you in search of a mentor to help you make a career switch? 

  • Do you want a coach to keep you accountable for pitching nonfiction essays? 

Next, give it a number. For your three skills, find a course, workshop, or coach that you would consider investing in. How much does that cost? 

  • Skill 1: ______________________

  • Skill 2:______________________

  • Skill 3:______________________

Total up the cost of those programs and divide by twelve, and you’ve got your monthly self-investment amount. 

We’ll show you what this looks like in action:

‍Let’s say Sara finds a persuasive copy certificate that costs $2,795. Udemy offers a content marketing course for $24.99. Sara also finds a personal essay course for $139.   

Here is a template Sara can use to figure out how much she needs to save:‍

$____ (Skill 1) + $____ (Skill 2) + $____ (Skill 3) = $2,958.99

$2,958.99 / 12 months = $246.58 per month.

If Sara is worried about going over budget, she can use the percentage rule to make sure it’s a worthwhile investment. 

$____ (Skill 1) + $____ (Skill 2) + $____ (Skill 3) ≤ 

$_____ (annual income) x ___% (the percentage you want to spend on education) ‍


In this step, you learned how you could make yourself more valuable and more employable. ‍

Which three skills did you pick to focus on for the coming year? How much can you budget for them?

Next, you’ll be investing in your future in a different way: retirement.

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