How to Build Your Freelance Strategic Plan: Three Steps to Success • Winning Solo

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Your freelance strategic plan can be the difference between longevity in this line of work and an early exit.

When you create your freelance strategic plan, you take the first step in building the business that you’d love to have. It helps you to focus, prioritize, avoid shiny objects and solve your biggest challenges.

Strategy is how I’ve made my living as an independent consultant for over 25 years. So I’ve spent a good bit of time thinking about how to develop a freelance strategic plan that is lightweight and effective – you know, something you’ll both build and use.

This post shares an approach to building your plan. My hope is that it will help you to feel more confident and in control of your independent business.

Creating a your freelance strategic plan is not easy – and I’d warn you away from anyone who suggests it’s a 30-minute exercise – but I’ve worked to streamline the process for you. As with most things, you’ll get out of it what you put in.

Why Build a Freelance Strategic Plan?

Here are six reasons to build a freelance strategic plan – even a lightweight, streamlined one:

Planning solves problems. I’ll go as far as to say planning is problem-solving. You are here, but you want to be there, and that’s a problem to solve.

Planning identifies goals and their relative importance. Good planning identifies not just what’s important to pursue, but what’s most important.

Planning sharpens your focus. It identifies what to do and – just as importantly – what not to do.

Planning forces you to make trade-offs. You can’t do it all. Good planning factors the constraints – most commonly, for us soloists, time and money – to develop a course of action that’s credible and realistic.

Planning saves time. When you’re working with a plan, you’re less likely to be distracted by shiny objects. A plan makes you both more efficient and effective.

Planning increases your odds of success. All businesses, including ours, are odds games. One of our tasks is to continually increase our odds of staying in the game. Planning helps you do that.

A Quick Note on the Horizon of Your Freelance Strategic Plan

You can build your freelance strategic plan on any horizon you like. My strong preference is quarterly.

I used to plan annually. Then I learned that a year is difficult to conceptualize and easy to procrastinate within. But 90 days is enough time to make significant progress on anything – and to hold yourself accountable.

Of course, we all have longer-term goals. If something can’t be fully realized in 90 days, simply identify the most important steps you can take toward that goal in the next quarter.

Switching from an annual plan to a 90-day plan immediately increased the effectiveness of both my planning and my execution.

With that, let’s turn to the steps by which you can build your Action plan.

An Overview of the “3 A’s” Freelance Strategic Plan

First, what is strategy?

I define strategy as “an integrated set of choices for winning.” It’s how you’ll achieve something that’s important to you.

Despite what some of my fellow consultants may argue, strategy isn’t a hidden base of knowledge that’s accessible only by a few intellectual elites.

On the contrary, you use it every day. Have you ever had to figure out how you’ll get two kids to simultaneous after-school activities in different parts of town, while also ensuring that your humans get fed? Strategy.

I call my approach to planning the “3 A’s,” because each of its key elements, conveniently, starts with the letter A. (These things don’t happen by themselves, people!) It looks like this:

In any kind of strategy, you must define where you are, where you want to be, and how you’ll get there – while factoring your strengths, obstacles and constraints. Your freelance strategic plan is no different – and no more complicated – than that.

Enough preamble. Let’s get started on the first step: Assessment.

How to Build Your Freelance Strategic Plan: Step One – Assessment

People often want to jump right into the “fun” stuff – the vision, the tactics, the shiny objects – without first taking stock of where they are. This is why many corporate strategic plans fail; they’re untethered from objective reality.

But assessment is crucial. Your freelance strategic plan must start with a clear-eyed take on where you are, including what got you there.

So this step is all about the past and present. But as you review the prompts below, your mind will invariably jump to the future – solutions, initiatives and the like. This happens to me too.

Here’s a simple trick: Open a “Parking Lot” document, app or journal. Capture ideas so you don’t lose them. But don’t get attached to them either. It may feel like a white-hot idea in the moment, but it’s useless if it doesn’t bridge the gap between where you are and where you’re going. And we’re not there yet.

Below, you’ll find the six areas I explore in an assessment of a freelance business. There are also a handful of prompts within each. These aren’t meant to be exhaustive, and there will be some nuances in your own business that aren’t captured here. But my aim is to provide enough to get your wheels turning.

Let’s assess!

1. Wellbeing

This is about fitting your freelance business into the fabric of your life. Everything starts here, so if this isn’t part of your assessment, you’re likely to miss something crucial. As Gregory McKeown says: “Protect the asset – and you are the asset.”

Which aspects of soloism create the most energy and excitement in me? The least?
Am I making time for my priorities – family, friends, exercise, learning, reading, quality sleep, hobbies and interests?
Which habits serve me well? Which habits can I improve on?
Which mental patterns serve me well? Which are holding me back?
Do I have a daily gratitude practice?
Am I creating memories?
Am I making progress toward the life I want to live?
Am I living my values through my work?

2. Performance

The focus here is the top-level state of your business – those objectives and measures that are most vital to the overall health of your independent business.

Did I hit my primary objectives? Why or why not?
Did I hit my secondary measures? Why or why not?
How did my revenue and margins split out, by service, type of client or other relevant categories?
To what degree did I stick to my last plan? Why?
What worked particularly well? Why?
What didn’t work as well? Why?

3. Marketing and Sales

Here, we’re assessing “the work that brings you the work.” This is very different from one freelancer to the next – so, again, use these prompts as starting points.

Which of my marketing tactics were most successful? Least successful?
By what channels or methods did each client find me?
How many valid inquiries did I generate, by service?
What was my closing rate, by service?
How did I perform on my networking, social media and website metrics?
To what degree am I attracting prospects who want to work only with me?

4. Clients and Projects

The focus here is on the work that that you won and executed. Assess both the nature of that work and the quality of your clients.

For every project in the past year: Would I do this exact project again next year? If yes, why? If no, what would I change?
What are the characteristics of the clients and engagements that I feel best about?
What was my effective hourly rate, for each project, each service, and in aggregate?
Am I doing the kind of work, with the kind of organizations, that I endeavor to do?
Am I pleased with the transformations I’m creating for my clients? Are they?

5. Strengths and Assets

Every company has strengths and assets, and your one-person company is no different. Inventorying these assets will lead you to choose better clients, better projects, and better marketing tactics.

What do I bring to the table? Think skills, strengths, mindset, habits and traits.
What are my advantages in the market?
How much time & money can I invest in the growth of my business?
Why should someone hire me? This can include awards, testimonials, client list, experience, proprietary processes and so on. (These proof points are often left to the Action phase – specifically, your communications – but that’s silly. They’re assets and they should be identified early.)

6. Time

As soloists, our time is our inventory. I’ve never known a successful soloist who was inefficient, and efficiency and effectiveness start with measurement.

Where am I investing my limited time?
What was my effective hourly rate, including non-billable time? (Knowing this figure helps you make a lot of other decisions, such as what to outsource.)
What is the split between my productive time and my administrative time?
How much total time did I invest in my business per week?
About how many hours per week are sustainable for me? (This is the normal run of things, when you’re doing good work but your hair’s not on fire.)
About how many hours per week are tolerable at “elevation” – temporary periods of high activity?

You may have realized you’re not tracking some of the things listed above, but that maybe you should be. Hey, look! Those are also things you can add to your Parking Lot.

There’s one more thing you need to do to close out your Assessment phase…

Write a Situation Summary for Your Freelance Strategic Plan

Yes, you heard me. You’re going to write an executive summary – to yourself.

Why? Because you’ve captured a lot of data. Made a lot of notes. Thought a lot of thinky thoughts. And if you don’t pull out the most important nuggets, this entire exercise was for naught.

Your goal here is to capture the key findings from your Assessment. You want a list of about three to eight.

Since this is for your eyes only, I urge you not to shift into corporate-speak. Write it to yourself, in natural language, and in the first person.

To give you a sense of what a Situation Summary looks like, here are a few takeaways from my own from the end of 2022:

I attracted eight high-value, high-impact consulting projects. Two were extended beyond their original scope. For all, I was the only vendor considered.
97.7% of my revenue came from repeat business or referral.
My effective hourly rate was nicely above my target, though this rate varies considerably across projects.
I hit all external deadlines, but did not reach my goals for my important-but-not-urgent initiatives.
I am proud of how I’m living my values through my work. But I’m not making enough memories outside of work.

It’s that simple. Note that I don’t indicate what to do next, since that comes later. In your Situation Summary, you want a “just the facts” take on your own business.

I’ve created some worksheets to help you through all three phases of your freelance strategic plan. To access them, just enter your email below.

With an assessment of where we are in hand, we can now turn our attention to where we want to be.

How to Build Your Freelance Strategic Plan: Step Two – Aspirations

Aspirations define the future that we want to create. They’re about where we want to be and what we want to achieve.

Aspirations can come in qualitative forms, like vision statements, and quantitative forms, like numeric objectives. Both are useful, when properly conceived.

But when they’re improperly conceived? We can run into the same problems that we see with weak corporate aspirations. These problems include:

Fuzziness

Some corporate mission statements claim that they exist to deliver “stakeholder value.” I’m always left wondering: Exactly which stakeholders, and exactly what do you mean by “value”?

Of course, as freelancers, we have the benefit of writing these statements for eyes only. But that doesn’t let us off the hook. Our own aspirations should be crystal-clear and unambiguous to us.

Competing Priorities

I’ve seen marketing plans with the “primary” objectives of increasing both sales and market share. But it’s possible, for instance, to grow sales while losing share. So, a reasonable question: If you had to choose, which one is most important?

You can probably see where this is heading, my friends. I’m going to advise that you identify one – and only one – primary measure of success for your freelance business.

Fantasy

It’s unlikely that I’m going to make ten million dollars in a calendar year, or write the world’s best-selling book on branding. These are fantasies, and I don’t spend any time entertaining them.

One reason we spent so much time on Assessment is that it provides us with an unvarnished take on our current reality. From there, we’re better equipped to choose aspirations that are ambitious yet realistic.

No Strong Why

By “why,” I don’t mean the vague statement of purpose that’s currently in vogue in the business world. I mean a defensible reason for selecting an aspiration instead of its viable alternatives.

A big part of selecting our freelance aspirations is answering the deceptively difficult question: “What is the most important thing I should be working toward?”

If we avoid those four mistakes, we’ll go a long way to shaping aspirations that will serve us well.

So let’s turn our attention to getting it right. Here are the three kinds of aspirations for your freelance strategic plan.

Aspiration #1: Your Personal Vision

You’ll want to write two vision statements – one for you, and one for those you serve. They’re both about the future that your business will help to create. Think in terms of three to five years from now.

This first one, your Personal Vision, is about what your business will deliver to you. You’ll manifest a better life by defining a clear picture of what you want it to be.

To write yours, start by free-writing within the following prompts:

What is my ideal future?
What does winning look like for me?
Where do I want to be in 3-5 years?
How does my work fit into the fabric of my life?
What’s the legacy I want to leave?
What’s the difference I want to make in my field or industry?
What’s important for me to achieve in this lifetime?
What are the deeper ideals I want to manifest through my business?
What values do I want to live through my work?
What is not important to me? Where won’t I invest my energy?

After a couple of free-writing sessions, step back and review. What are the most important aspects of your Personal Vision? How could you capture them in a succinct sentence or two?

Remember: It’s not unreasonable to expect your business to be a vehicle for a better life. In fact, that’s exactly the point. If your solo business doesn’t improve your life, why bother? So you’re not being “selfish” by focusing on yourself.

And we’re about to turn our attention to those you serve.

Aspiration #2: Your Service Vision

As with any company, if your freelance business accrues benefits only to you, you won’t have a business for long. So we must pair our Personal Vision with a Service Vision.

Your Service Vision is about what your business will deliver to others. The first step in serving your clients is to define how they will win.

Start with free-writing within the following prompts:

What are the characteristics of the clients, brands and businesses I want to serve?
What does winning look like for them? What are they trying to achieve?
How does my work fit into their larger aspirations?
What’s the difference I want to make for my clients?
How will I serve, transform, enable and/or improve them?
What challenges and obstacles can I help them overcome?
What are the deeper ideals they are pursuing that I can help them achieve?
What values can I help them live through our partnership?
What is not important to them? What won’t I deliver?

Again, after a couple of free-writing sessions, step back to review what you’ve captured. What are the most important aspects of your Service Vision? How could you capture them in a succinct sentence or two?

Example: My Personal Vision and Service Vision

To give you a sense of what these vision statements can look like, here are my current versions for my consulting business. Combined, they are a total of 41 words.

My Personal Vision:

I am a recognized authority in challenger branding, delivering high-value outcomes that allow me to work a reasonable number of hours while I pursue balance and joy.

My Service Vision:

The brand leaders I serve have the guidance and tools to achieve outsized success.

Note that I’m not trying to capture every single aspect of what I do – just the highest-level, most important things.

In my Personal Vision, I’ve captured where I want to play (high-value outcomes for challenger brands), how I’ll get there (building authority), within what constraints (a reasonable number of hours), and what it’s all for (balance and joy).

And in my Service Vision, I’ve captured the idea that I’m helping my clients to play bigger, while giving myself plenty of room to define “guidance and tools” as my business evolves.

Also note that there’s not a single numeric objective in either. That comes next.

Even though I just shared mine with you, remember: Your Personal Vision and Service Vision are for your eyes only. So your challenge is to capture a pair of vision statements that are clear, meaningful and motivating to you.

Aspiration #3: Your Business Objectives

Your Personal Vision and Service Vision were about qualitative visions for the next three to five years. Your Business Objectives are about quantitative measures of success over the next year.

Here, you have two tasks:

Identify one – and only one – primary measure of success for your freelance business.
Identify the secondary measures of success that you will also track.

Our freelance businesses are all a little different, but some common primary and secondary measures are:

Total revenue
Revenue per working hour
Average revenue per project
Total profit
Number of inquiries or qualified leads
Closing rate
Newsletter subscribers
Website visitors
Social media followers, impressions and/or engagement
Average weekly working hours
Average weekly hours on marketing and business development

A great place to identify primary and secondary measures is the Assessment you completed at Step One of your freelance strategic plan. And, of course, each of your marketing initiatives should have one primary measure, and maybe a few secondary measures, of success.

To help decide which objective is primary, pair up two viable alternatives and ask: Which of these would it hurt most to fall short of? The one you’d hate to miss most is a good candidate for your primary objective.

For many of us, the primary measure of success is a revenue goal. But it’s not the only valid measure. Ultimately, it’s up to you to determine what matters most for you and your business.

You want your primary objective to be ambitious but realistic – something that will motivate you, but that you also have a reasonable chance of achieving.

This step is complete when you’ve identified:

One, and only one, primary objective.
As many secondary objectives as you deem useful. (But not too many! You don’t want to be mired in tracking when you should be executing.)
The method and timing by which you will track your progress toward each objective. (I track most of mine monthly.)

To get a free set of worksheets for all three phases of your freelance strategic plan, just enter your email below:

Assessment defines where you are. Aspirations capture where you’re going. Action establishes how you’ll get there.

So let’s turn to Action.

How to Build Your Freelance Strategic Plan: Step Three – Action

This is the “guts” of the plan – the few things that you will execute with excellence in order to get you to where you want to be.

Two points of emphasis here:

“Few things” – I once tried to execute a plan with 10 “key” action items. Nothing got done, at least not in a way that moved the needle. Help yourself fight overwhelm by being selective up-front.

“Execute with excellence” – You won’t build a remarkable freelance business by doing things at parity. As with any kind of strategy, execution makes all the difference. Being selective helps here too.

There are many reasons your action plan can fail. To help prevent failure, here are four truths for you to consider:

Your objectives are unique to you.

So, you must ask: Which initiatives will work hardest to get me to those objectives?

The Aspirations you created at Step Two are undoubtedly more nuanced than “more clients.” (At least they should be!) By keeping your unique aspirations in mind, you’ll select smarter strategies.

Your strengths are unique to you.

If you’re a strong presenter, you might make this part of your plan – for example, presenting to local business groups. If you’re a writer, you might gravitate toward blogging or LinkedIn posts. If you’re a people person, you might make networking your cornerstone.

Don’t force yourself to swim upstream. All else held equal, you’ll do a better job of executing things that leverage your strengths than things that don’t.

Your obstacles are unique to you.

Strategy, at its core, is problem-solving. And the more specifically you can identify your problems, the better you’ll be able to solve them.

This is why I stress the importance of Assessment (the step everyone loves to skip). Only through diagnosis can we identify the obstacles we must overcome.

You have limited resources.

Specifically, we freelancers tend to have small budgets and limited time. We can’t do it all. So we have to be deliberate and selective.

For all the above reasons, one of the biggest traps to avoid is simply borrowing tactics from others. Seek inspiration from wherever you can find it, but remember: Strategy is situational.

If it works for others, that doesn’t mean it will work for you. And if it doesn’t work for others, it might still work for you – because you’ll do it in your own way.

Action Plan Part 1: Articulate Your Guiding Policy

Your Guiding Policy identifies an overall approach for overcoming your obstacles, leveraging your strengths, and realizing your aspirations. Ideally, you’ll capture this in a single sentence.

I can’t overestimate the importance of capturing a Guiding Policy – even for a plan that’s for your eyes only. It helps you to prioritize, and it keeps you from chasing shiny objects. This is where the process of focusing begins.

To give you an example, my current Guiding Policy for my consultancy is:

Drive qualified inquiries by elevating my authority.

I’ve linked a preferred approach (elevating authority) to a near-term goal (drive inquiries). Anything that doesn’t fit within this Guiding Policy is a candidate for removal from my plan.

Action Plan Part 2: Establish Your 90-Day Priority

Your 90-Day Priority defines the one most important thing for you to achieve in the coming quarter. It often takes the form of a specific project or outcome.

For example, my current 90-Day Priority is for my consultancy is:

Define and execute my LinkedIn content plan.

This is a specific project that I’ve prioritized in the name of driving inquiries and elevating authority.

Note that it’s typical to have a hunch at Step 2, and to revisit this once you’ve completed Step 3. In other words, you may spend a little time building your plan before you finalize your 90-Day Priority. That’s fine. Strategy is rarely a clean, linear process.

Action Plan Part 3a: Identify the Contenders for Your 90-Day Plan

Here, we identify the initiatives that will bridge the gap from where we are to where we want to be.

Typically, for freelancers, there are three types of initiatives:

Marketing

This is “the work that brings you the work.” It can include initiatives like newsletters, social media, networking, speaking gigs, writing for publication and advertising. These may be brand-new initiatives, or continuations of things that are already working for you. These typically form the bulk of your plan.

Upskilling

These are learning initiatives that help you to do better work or better marketing. For example, as part of my 90-Day Goal to “define and execute my LinkedIn content plan,” the first step will be to complete a course on how to do it right. From there, I’ll define the specifics and execute.

Building

These are typically new offers, something you intend to sell. Examples include a digital course, a coaching program or an e-book. Many freelancers won’t have any initiatives in this category, which is fine. And for those that do, I recommend strict time-boxing. Given the very low success rate of most products (digital or otherwise), you want to make small bets with your time. You’d hate to invest three months into something that nets you a total of $500 in sales.

And initiatives will typically take two forms:

Projects

These are initiatives with a defined start and finish. Examples: Publishing newsletters (each one is a small project unto itself) or completing a course.

Habits

These are ongoing initiatives. Examples: Monthly social media planning or weekly networking outreach.

Right about here is where I always get the question:

But how do I know what will work?

Answer: You don’t.

You’ll never know, in advance, what will work for you. We’re dealing with human nature, including your ability to execute. There are no guarantees in marketing, and anyone who says otherwise is either misinformed or trying to sell you something.

So let’s ask a more productive question:

How do I choose what’s most likely to work?

This is a judgment call, which is the case for any strategic plan.

But here’s some direction to help:

First, start with your long list of ideas and initiatives.

This is where your Parking Lot comes in handy.

If your problem is that you don’t have enough (or any) ideas that feel viable, try these options:

Brainstorm around your top five priorities. What are some specific ideas or initiatives that would help you to become more efficient, more effective, more connected, more sought-after, and/or more expensive?
Ask a fellow freelancer. Share your situation and your challenges, and ask how they’d move forward.
Google it.

Your goal is to have more good ideas than you can execute in the next 90 days.

Second, whittle that list down. Ruthlessly.

Ask the following eleven questions:

What’s already working? (If your current plan is doing what you need it to do, at least 80% of your next plan is continuing this work.)
Which will put me in front of people who are in a position to hire me?
Which will work hardest to reach my aspirations?
Which will leverage my strengths, skills and passions?
Which will solve my problems and overcome my obstacles?
Which will work within my resource constraints?
Which must be executed before other initiatives?
Which will deliver the best return on my time?
Which will work most quickly?
Which will deliver the best long-term returns?
Which am I most excited to execute?

Based on your answers to the above, I recommend you sort your initiatives into three categories:

“Not For Me.” These are ideas that don’t work with your goals, strengths or constraints, or that you just aren’t that excited about. Drop them to the bottom of your Parking Lot or delete them forever.

“Maybe.” These are ideas that have some potential, but other ideas feel stronger. Move these Maybes to the top of your Parking Lot.

“Let’s Do This.” These are the few ideas that you’re feeling best about.

Pro-tip: If it’s not a “Let’s Do This,” it shouldn’t hit your final plan.

What’s that, you say? You still have too many ideas in the “Let’s Do This” category? Run through the 11 questions again, looking for ideas that can be moved to the “Maybe” category. Remember: If everything’s a priority, nothing is.

Action Plan Part 3b: Break Down & Assign to Your 90-Day Plan

If you’ve whittled down your list of ideas ruthlessly, you should have no more than five or six initiatives to tackle in any given 90-Day Plan (often fewer).

Your next step is to assign priority and timing. This little bit of planning goes a long way toward ensuring that you’ll execute your plan.

To help yourself succeed, follow this simple rule:

No more than two priorities per week.

This forces you to prioritize – and it helps you to fight overwhelm.

Enter your email below to get a set of 90-day worksheets already set up for you, with two available slots per week.

Here’s how to assign priority and timing:

First, plan your time off. If you’re doing vacation correctly, you’re not doing any real work during that time. So block off this time entirely – mark both available slots as “vacation.” If you’re taking a half-week off, block off one of the two slots for that week.

Second, add in your ongoing commitments. For example, I publish my freelance newsletter twice a month, so every two weeks, one of my available slots is reserved for Soloist Sundays.

Third, plan your initiatives, starting with the top priority. Help yourself out by breaking your big rocks into small rocks. If an initiative has several steps, break these down individually. I recommend the “90-minute rule”: If something can’t be completed in a single 90-minute session, break it down until it can.

Example: For my LinkedIn content plan, one small rock is completing the course. The next small rock is defining my overall approach. The third small rock is creating my content, which I will batch monthly – in other words, a recurring slot on my strategic plan, once a month.

Important: Leave some slack in your plan. You don’t have to fill in every available slot. I usually front-load my 90-Day Plan, leaving my slack in the back. If client work ramps up, I can bump my own initiatives back a week or two.

At the end of this step, step back and review your plan. It should feel challenging but doable. Most importantly, it should feel like it will move the needle for you in a meaningful way.

So ask yourself a very important question – one that I always ask my clients when building strategy with them:

Do I believe my own plan?

If not, make the necessary changes. Don’t proceed until your answer is a “hell yeah.”

Action Plan Part 4: Identify Your Key Measures

The final step is to determine how you’ll measure the success your initiatives, plus any other key metrics for your freelance biz.

These often flow from the secondary measures you established in Aspirations, but new ones sometimes present themselves as you build your plan.

For example, I haven’t been tracking my LinkedIn metrics at all. But to gauge the success of my LinkedIn content plan, I’ll want to track how often I post, and the resulting changes in views, engagements and followers.

I set aside a little time at the end of each month to track these measures and course-correct as needed.

Summary: Your Freelance Strategic Plan

If you’ve followed along, you’ve identified:

An Assessment of where you are and what got you here.
Your Aspirations for what you want your freelance business to do and be.
The Action plan that will bridge the gap.

And that’s everything you need to run your freelance business.

Remember: Strategy is an exercise in problem-solving. It helps you to overcome your challenges and obstacles so you can get where you want to be. And it keeps you focused on the right things, so that you’re not distracted by the wrong things.

I’ve created some free worksheets to help you along:

Here’s to a freelance business that you’re in control of – instead of one that’s in control of you.

Your time is valuable, and I hope I’ve rewarded it. If so, your shares are greatly appreciated, as I try to spread the gospel to as many freelancers as possible.

Need some help building a lightweight and effective plan for your freelance business? I have a limited number of slots available for 1-1 coaching. Click here to find out more about how my customized coaching can help you level up.