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Brennan Dunn

Start A Freelancing Business

Just starting out or thinking about it? Here you'll learn how to adopt the right mindset to run your business and get your first few clients.

Branding and Positioning

The way you position and present yourself to your clients can make or break your chances with a prospect. Learn how to do position yourself the right way.

Marketing Your Business

Clients are the bedrock of any freelancing business. Learn how to reliably generate high-quality project leads.

Pricing Your Services

How you price and pitch yourself affects the quality of your clients and your income. Learn how to charge more and close more projects.

Writing Proposals That Win You Projects

Writing (and winning) proposals is critical to closing deals. There's no point in having lots of project leads if you don't know how to close them.

Project Management For Freelancers

Once you've sold a client on working with you, learn how to ensure that you consistently deliver great results.

Running Your Freelancing Business

All the advice and tools you need to run a profitable and sustainable freelancing business.

Work/Life Balance For Freelancers

You CAN freelance without sacrificing your sanity. Learn how to balance your life and your work.

Productizing Your Services

What if you could sell your services the same way you'd sell a product? Learn how to level-up your freelancing with productized consulting.


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Top Recently Published Articles & Guides

What’s The Best Invoicing Software For Freelancers?

I get asked often what I recommend for invoicing clients. There are a lot of offerings. After all, you could do it the old fashioned way and use one of those invoice templates that Word and Pages offers (do people really use those?) But you’re probably using, or want to use, software that is built around the act of invoicing.

What do you need your invoicing software to do?

Are you a solo freelancer or a shop of 15? We all have different needs. Some of us, like designers who purchase stock photos and those who need to travel, need robust expense tracking. Or maybe you want integrated time tracking, and the ability to estimate new projects.

Before you choose a product, make a list of what you need your invoicing software to do. For example, my needs are pretty basic. I need a tool that has projects, and I need the ability to log time in these projects and generate invoices from unbilled time. Bonus points if it’s super easy to see who owes me what and when.

Desktop or Web Based?

Sometimes this is more a philosophical or aesthetic decision. I’m obviously biased towards web based software – Planscope can’t be downloaded. I personally don’t trust myself to keep my project information on my laptop. The chances of theft or hard drive failure, while thin, are still there. I trust that web application providers do daily backups and take care of warehousing my data. After all, that’s their job (and why I’m paying them.) And yes, we’re extremely paranoid and proactive about securing Planscope’s data.

I’m inclined towards web based software because they tend to run well in any desktop browser – meaning I can access it on my phone, iPad, laptop, or whatever connected computer is closeby. They’re also more likely to have some sort of collaborative abilities, a must if you’re not working solo.

List of some options for invoicing software:

  • Harvest This is the product my team and I use. Features include time logging and running timers, reports on time logs (by client, project, staff, and so on), generated and manual invoices, recurring invoices (great for retainer agreements or hosting invoices), and expense tracking.
  • Freckle Written by two friends of mine, Amy Hoy and Thomas Fuchs, Freckle is a beautiful and simple product meant to make the barrier of logging time as minimal as possible. It also boasts an emphasis on providing reflective analysis on your working habits: Are you spending too much time on unbillable time? Are you lagging on certain days? Features include dead simple time logging, quick reporting, a pulse view that visually shows your work output on a calendar, and invoicing.
  • Freshbooks Freshbooks is a full featured product that satisfies a lot of the needs most small businesses have. Two features set them apart: They integrate with a lot of payment gateways, which is super useful if you accept credit card or echeck payments. They also can snail mail invoices, if you have strange, enterprise-y clients who requires such things. In terms of features, they’re pretty similar to Harvest: Time logs, invoices (recurring and generated), reporting, and expense tracking.
  • FreeAgent A lot of our users across the pond use FreeAgent, which seems to be the most popular offering in the UK. Unique to most of the other time tracking and invoicing tools, they integrate with bank accounts and help you out come tax time. Other features include time logs, invoicing, drafting proposals, and expense management.
  • Billings The only non-web based product on the list, Billings is a Mac and iOS application. Years ago, when the invoicing landscape was much more barren than it is today, I used Billings – and it’s obvious that it’s come a long way since then. Features include time tracking directly from your operating system, generated and recurring invoices, reporting, and a native iPhone client.
  • LessAccounting Written by my super friends Allan Branch and Steve Bristol, LessAccounting has everything a small business needs for bookkeeping. I don’t believe they offer time tracking, but they do let you generate invoices (remember: bakeries, record shops, and other companies that don’t bill for time use it!) Besides invoicing, they integrate with hundreds of banks, let you create project proposals, track vehicle mileage, run reports and manage contacts.
  • Harpoon Harpoon includes all the features you’d expect from a powerful, online invoicing system. But Harpoon sets itself apart with some very practical financial planning and goal-setting features. You can set a financial goal for your business and then map out your expected and collected revenue on a yearly calendar as you work towards meeting your goals. Harpoon also provides an assortment of financial metrics you don’t find in most other invoicing apps, including letting you know when it’s safe to take a vacation. You also get a robust time-tracking system, expense tracking, project scheduling, and accounting reports.

Other time tracking tools (that don’t have invoicing)

  • Mite This is another European product, which has worked hard to design a very clean, very simple interface that stays out of the way. Features include time logs and running timers and reporting.
  • Tick Tick is a simple time tracking tool that places an emphasis on fitting the time you log within a project budget. Features include easily adding time, quickly seeing what budget is remaining on a project, and reporting.

How To Convince Your Clients To Pay You Hourly

If there’s one thing I’ve ever regretted while freelancing, it’s having been suckered into fixed bids – or to put it plainly: projects where the client has a vague idea of what they want built, and wants you to read their mind and tell them exactly how long and how much it will cost.

Of course, it’s never clearly spelled out like that when contract negotiations are happening. You pretend you know exactly what your new client means by “messaging feature”, and your client thinks they have any clue how that feature will work. After all, you want to win the contract and for the client to sign on the dotted line.

But then things get real, and that messaging feature turns into a can of worms you could never expect. And because you’re on the hook for building that feature at a fixed cost, your client’s going to reshape that feature until it satisfies whatever is floating around in their head at that minute. The more hours you work, the less profitable that feature is.

I’ve heard a lot of excuses about why flat project fees are superior. They include:

  • It’s hard for clients to appreciate the value they’re receiving for your hourly fee.
  • It’s hard to justify raising your rates.
  • You don’t need to track your time anymore!

The underlying idea in those excuses are that your clients don’t respect you as a professional, and you don’t respect yourself. The first is countered by simply communicating with your client what you’re getting done. The second’s the easiest: Supply and demand. Your time (the supply) is limited; if more people want to work with you, you raise your rates. Last, if you’re not tracking your time, even if you’re working with a flat fee, you’re not being accountable to yourself and your client.

How I get my clients to pay hourly

Would you ever walk into a custom furniture store, ask the price of a custom made bed, and put up with “Hmm… Well, we’ll see how long it takes. I’m not sure. But we’re going to charge $100 an hour and we’ll send you an invoice when it’s done.”

Clients, like the rest of us, budget their money, and it’s important to respect that. When you charge hourly, you run the risk of going over – or under – project budget (usually over, because scope always gets added.) It’s your job to get into your client’s head as much as possible, and to attempt to comprehend exactly what they need built. Assumptions are fatal. Don’t ever assume that you know what the “messaging feature” is!

Before I give you the stump speech on winning an hourly contract, here are a few concepts you must master:

  • A few posts ago I discussed a few ways to create better estimates. The last takeaway is most important: For any decently sized project (read: over a week of full time work), charge for an estimate. You’re a midwife of other people’s ideas. You take vague concepts that are floating around your clients’ head and bring them to life. This will create a strong list of deliverables, and will also be granular enough that you should be able to put together a decent time estimate.
  • Split the estimate into must-haves and want-to-haves. Prioritize accordingly. This will ensure that everything that needs to be in place will be there before the budget burns out.
  • Commit to staying in constant communication. Sure, Planscope helps this happen, but good ol’ fashioned email works just as well. You need to ensure that value is being constantly correlated to the amount of time you work.
  • Explain to your client that dreaming up a project is like gazing into a crystal ball. The reality is as the project evolves, scope will inevitably expand or contract around certain features, and because you’re charging hourly and burning budget, you’ll be able to steer quickly towards what the business needs dictate.

Finally, when you get pushback when explaining your hourly rate, here’s your line: “I understand your concerns. I do. But I’ve worked on a lot of projects, and can tell you with certainty that what you’re wanting built will change over time. An hourly rate will keep me from pushing back each time you ask for a small change or to go towards a new direction – which believe me, you will. I want to see your product succeed, and you need to trust me to make that happen, because otherwise this will be built based on what you want today, instead of what you need tomorrow.” And then list off some of the concepts above: You’ll constantly clue in your client about what you’re working on and what it’s costing, and serve as a consultant, helping them deliver the best product for their buck.

I still don’t win them all, but my success rate has gone up substantially since I started focusing on why hourly is better for them, and not just me. And I no longer have had to lose money for time I’ve worked, which is just plain stupid.

6 Tips To Help You Create Better Estimates

Estimating is hard, risky, and usually imprecise. But it’s something developers and designers need to produce before winning a contract. I’ve probably sent out about 200 estimates in my career, and have closed at least half of them.

Regardless of whether you bill hourly or flat bid your projects, every client is going to have a number in mind and a project budget set aside. If scope is added to your project or things change course, they’re still going to keep that number in mind – trust me. So it’s important for you to arm yourself with a reliable estimate, and cover your bases in the event that things don’t end up as peachy as you imagined.

Here are 6 things that I’ve learned over the last few years that have helped me mitigate my risk (no one should ever lose money on something they were hired to do!), and have assisted me in producing happy clients who come back for more.

Double your initial guess

Most of us are optimists. We like imagining the future in ideal days: the sky is clear, birds are chirping, our code works just as we intended, and there are no distractions. Yeah right!

I’d always rather come in under budget than over, and the best way to do that is to estimate according to the Laws of Nature: the time we spend writing code or designing is not linear to our progress.

Hindsight is 20/20

I rarely come across anyone who does post-mortems on their projects, and assesses whether they were too liberal or conservative in their estimates. If you don’t do this, you really need to start. What I like to do (and what Planscope does for me) is to compare the time estimated with the time actually worked, and develop a ratio of assumption : reality. Overtime, I can start allowing this to influence my estimating, so that the deviation between the estimate and the time actually logged is negligible.

Don’t eat more than you can chew

The bigger the project, the harder it is to estimate accurately. This is why I prefer dividing projects into digestable milestones, with each milestone containing a set amount of tasks.

Imagine if you were going to walk from San Francisco to New York. If I asked you where you’d be after a month, you’d probably reluctantly point to someplace in the Midwest. Now if I asked where you might be in three days, the room for error is going to be significantly less. We should do the same with our projects, and encourage our clients to not dwell of big ideas, but instead, realistic, small milestones.

Identify what’s subjective

Whenever there’s a design component of what you’re doing, remember that design is subjective. The gulf between “Implement a reset password feature” and “Design the landing page” is huge. The first is pretty straight forward, and leaves little room for interpretation. The latter, on the other hand, is only complete when the client thinks it’s complete.

If you are going to work on a fixed bid basis for development, if you’re asked to do anything subjective – like designing a landing page – ask to bill that hourly, and explain why. Each hour you spend revising means lower profit, and your client might think they have the right to constantly revise until they’re 100% satisfied.

Never assume anything

I worked on a project a year ago that wanted users to be able to join user-created groups. Simple enough, I thought. Immediately I started thinking about join tables and the technicals of what happens when clicking “Join Group” or “Leave Group”. But what I missed was that my client really wanted a feature that included moderation, group owners being able to send out invitations, and so on.

I sold the feature based on my naive assumptions, and paid for the consequences later. Never assume you know exactly what your client wants unless you actually do.

Don’t offer free estimates

When you think about the product of your work, you’re likely to think about the obvious: the code or designs that you produce for your clients. Most estimates (unless you’re handed a spec sheet and wireframes) are the product of leveraging your expertise as a consultant to convert some wishy-washy idea of what your client wants into clear deliverables. And this is valuable.

I let my clients know that they’re more than welcome to take my estimate (or “roadmap”, as I like to call it) to any developer they want. But I’m not going to invest hours and energy into delivering value with no guarantee that I’ll be reimbursed.

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