Freelancer Flow Series: My Freelancing Toolbox

Transitioning from a permanent hire position to freelancing can be a stressful experience for even the boldest of people.

There is a laundry list of things to get done: Figuring out how much you’ll charge, sourcing work, closing contracts, invoicing, networking, tracking your time, and so much more.

Building a set of tools for handling your day to day tasks is an integral part of making a successful transition.

Everyone’s optimal workflow will be a bit different but these are the tools I’ve found are integral to my day to day operations.

The Tools


What’s It’s For: Scheduling

For scheduling, Calendly really can’t be beat.

Calendly allows a client to visit an event link and block a period of time for a meeting. The timezone’s are all handled by Calendly which makes it easy to schedule with people across the world. For example, if the client is in EST it will show the calendar in their TZ and then convert it to your TZ when it’s added to your calendar.

It will also update your calendar when the event is booked (Google, Outlook, Office 365 or iCloud calendar supported).

There are tons of other useful features, like placing buttons on your website or setting up a branded link (like

Cost: Free to $12 a month

If you only require a single event and don’t need to accept payments or other complex features, their free plan works great.

Their paid plans start at $10 a month, $8 a month if paid annually.


What It’s For: Digital Signing for Contracts

Faxing your contracts or signing them digitally in a PDF viewer is… very 1998.

Hellosign allows you to upload a PDF, tag the signature and date slots, and then send an email requesting that it’s signed digitally. Everything is handled in a few clicks on both sides for both the client and the the freelancer.

Cost: Free to $40 a month

Hellosign’s free plan allows you to sign 3 documents a month. If you require more features and documents, you can upgrade to their free plan for $15 a month ($13 a month if paid annually).


What It’s For: Business Phone Service

If you’re just starting off, you can likely get away with just using your personal phone.

I’ve found it looks more professional to have a work only phone for client calls.

I looked at a lot of different companies and of then, Nextiva offered the most useful features at a great price point. Their support was also pretty on point.

Cost: From $20 to $30 a month + fees

Nextiva doesn’t have a free plan but they’re pretty inexpensively priced anyway. You can probably get away with their cheapest offering.


What It’s For: Invoicing, Estimates, Accounting, tons more

Waves is a one stop shop for handling invoices, estimates, payroll, and basic accounting. You can easily generate an invoice and send it to your clients email to be paid with credit card or ACH (From supported banks)

Credit card transactions cost 2.9% + $0.30, ACH transactions cost only 1% with a $1 minimum fee. This is the same price as Paypal but with a ton of added features. ACH payments are even cheaper than Paypal.

I will admit there a few places it isn’t great, in particular recurring bills (Huge pain) and accounting features in general. I’ll likely pair this with a more full fledged accounting suite later (Would love to hear your suggestions in the comments!)

Cost: Aside from transaction fees, completely free!

Pretty difficult to beat considering it’s at worst the same cost as Paypal but with more features (And can even be cheaper if the client uses ACH!)


What It’s For: Time tracking

It tracks your time: That’s it :).

I generally group my clients into their own category, with projects for each client, time is tagged as uninvoiced or invoiced (So I can properly invoice at the end of the week).

Cost: Free with paid plans

I haven’t yet found a need for their paid plans so can’t comment on them. The free plan has plenty of features and works pretty well.

Autohotkey (Windows) or Autokey (linux)

What It’s For: Text expansion

You likely type many of the same sentences a day. Greetings, information on what you do, signatures, phone numbers, and more.

Instead of having to handle all that manually, you can write a simple script that will convert a short keyword to far more text.

Something like “mynum” to your number, “calcon” to your Calendly link, or “mysig” to your signature.

This is a terrific time saver when you’re sending emails or proposals.

There are similar solutions for Mac/OSX.

Cost: Free

Free.Both Autohotkey and Autokey are FOSS (Free Open Source Software)


What it’s for: Webhosting, email

You’ll need somewhere to host any website you have and somewhere to handle your email.

MDDHosting is my personal choice, though any shared host will do. You can also choose to host your website yourself, though there is almost certainly no need for it.

I chose MDDHosting because it’s a Non-EIG company, has reasonable support, and the pricing is not bad either.

Note: I have no affiliation with MDDHosting other than as a satisfied customer. The link above is a standard link, not an affiliate link.

Cost: Price varies. Starts at $2.25 a month.

Their most basic plan starts at $2.25 for a single domain with up to 5 MySQL databases.

They have a number of other plans if you require more capacity.


Hopefully this article helps build out the tools you require for a successful transition to freelancing.

If you or your client’s ever have a need for a Linux Sys Admin/Automation Engineer I hope you’ll keep me in mind!



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