Strategic freelancing: How to approach your career like an entrepreneur

To be a successful freelancer or independent consultant, it’s essential you approach your career like an entrepreneur. This means you need to have the mindset of building a business as opposed to just picking up ad-hoc projects that may come your way. Having this approach from the beginning will bring security, sustainability and growth in earnings and differentiate you as a professional as opposed to a ‘gig’ worker!

Running your career as a real business allows you to think big and have a long-term view. For those who don’t do this and only think as far as their next project freelancing can become quite an anxious existence with the end of each project feeling like it could be the last. These characteristics aren’t conducive to longevity, wellbeing or success.

Create a business plan

As you would if you were building a business, ensure you have a business plan. Just because you’re the sole proprietor doesn’t mean this isn’t required. Below are some of the things you should consider.

  • Your value proposition:  What is the unique value you’ll provide to your clients
  • The problem/needs you’re addressing:  What specific needs can you address and solve for your clients, what is it that you have, either experience or skills, that allow you to add value to them and respond to these needs
  • Target market and competition:  Which clients are you going to be selling to, and what other choices do they have? How are you going to serve them better than the alternatives?
  • Sales and marketing:  How will people learn about you?  What marketing techniques can you use? How can you leverage your network for referrals? What collateral do you need (e.g., website, profile, presentation, case studies)? You need to figure out where your target audience is and go there. It needs to be easy for them to find you when they need you
  • Budget and sales:  Do some forecasts of sales and outgoings. What will your margin be on each project? Will it be enough to sustain you and your family as well as help you invest in growth/save for the future? How many projects will you need to deliver to make a profit? How long can you sustain without being on a project? Use these figures to define what ‘success’ means from a commercial point of view
  • Milestones:  Have a defined roadmap with key milestones needed to achieve your goals. Each milestone should be defined by what it’s important and what is required to achieve/reach it
  • Partnerships/networks:  What other people or organisations could support your business? Industry bodies, other freelancers in your field of expertise, freelancing platforms, personal and professional networks for referrals and support

Continuous development

This is another essential component. Highly valued freelancers are continuously investing in their own development, skills enhancement and knowledge. Identify the key skills and expertise that will help you add more value to your clients or address gaps that may be leading you to lose projects or not earn the rate you want to be earning and find ways to add these to your arsenal. There are multiple ways to do this, and not all of them require you to spend a lot of money:

  • Read, research and gather insights. Through both desktop research and speaking to relevant individuals and businesses in your field, you can ensure you have a deep understanding of your market, current trends and developments and the things your clients will be thinking and worrying about. Ensure you develop your own point of view as this will help you have meaningful and rich conversations. All of this allows you to gather knowledge and anecdotes that will demonstrate your understanding and credibility when interacting with prospective clients
  • Leverage your network. Use the people around you to learn, develop your knowledge and understanding as well as identify areas where you could enhance your skills and expertise
  • Online courses. There are a large number of high-quality and affordable e-learning courses that can be done which can help develop base knowledge
  • Projects. Delivering projects is the best way to learn, therefore, sometimes it is worth taking a project which may not give you the fees you want to earn but does give you an opportunity to learn, experience a new market or industry and ultimately help you increase your attractiveness and value in the market for the future. Your portfolio of projects is a huge part of what sets how you’re viewed. Some projects are a stepping-stone to a bigger win as opposed to being the big win themselves


You need to be able to get in front of clients to win projects. Therefore you’ve got to ensure your target clients have every opportunity to be aware of your existence, the services you offer and what problems you can solve.

  • Digital presence: A strong and professional LinkedIn profile, website and twitter account are good assets to have in place. On LinkedIn try and be active, write thought-pieces and articles about relevant topics your clients would be interested in. Build a network of relevant people and organisations in your eco-system. On Twitter, as a minimum follow your target clients and prospective buyers to gain insights. For your website, you can host content, project case studies, client references/feedback, your current CV, etc.
  • Platforms: Be present on freelancing platforms that provide access to projects. Outsized, TopTal, and others are all services that try and match freelancers with relevant project opportunities.
  • Cold outreach: Don’t be scared to reach out to your clients directly. A well-crafted message can often deliver great results and at least get you a meeting.
  • Referrals: Make sure your peers, ex-clients, professional and personal network are all willing referrers of work. Word of mouth is still a very powerful way for freelancers to win projects.

Culture and brand

Being a professional means that you conduct yourself in a manner that reflects confidence, credibility, reliability and ethics. Clients want to work with people they feel comfortable with, whom they can trust to deliver and behave in a way that is positive and constructive and who brings knowledge and expertise that goes beyond their internal capabilities.

Having the right skills and expertise is expected, however, beyond this, how you dress, whether you’re on time or not, the way you communicate, the language you use, your demeanour, body language and energy – these are all critical factors that influence a clients decision to hire a consultant. These all contribute to your personal brand and reputation in the market.

When a client buys a consultant from the external market, they are putting their own reputation on the line. Your conduct will reflect on them and either enhance or negatively impact their standing in the organisation. Therefore, the focus must be on having standards that go beyond their internal expectations as opposed to just meeting them. Your key measure of success on a project is ensuring a client would hire you again and refer you to another client.

Be on top of your admin

Make sure you have an understanding of how freelancing works. So things like contract terms, e.g. no holiday pay, liability clauses, non-compete etc. are all things you should familiarise yourself with. You need to have a view on what contract terms you’re happy with and what terms you’re not. Invoicing is another one, ensure you have an invoice template, you understand how tax works for freelancers in your particular market, you know how to fill in a timesheet and evidence the work you’ve done. Think about what insurance and savings you need to have in place to cover the fact you won’t get holiday or sick pay in most circumstances or any company benefits. There are a number of tools and services that can simplify many of the tasks you can’t escape, such as accounting and more.

Define your objectives

Some freelancers are happy as long as they are earning the fees they need. The focus for them is doing interesting projects and earning a good enough income out of those projects to have a good life. Others are keen on developing a business, collaborating with others to deliver larger projects and potentially at some point creating a consulting firm of their own. Once they’ve built a firm the focus is then on growing the firm, merging with a larger firm or maybe even getting bought. Many freelancers, due their innate entrepreneurial skillset and spirit, also end up using the wealth they accumulate to launch completely different businesses, products and services. Some return to permanent employment. There is no fixed path; however, it’s useful to have a view on the path of your choice, bearing in mind that this may change and that this is ok. Having a direction and objective will help create focus and help guide the decisions you make.

Final thought

By taking the time to do some of these things you significantly increase your chances of achieving that goal of being your own boss and enjoying all of the benefits a career as a freelancer offers: Flexibility, diversity of work and experiences, high earning capacity, control, accelerated learning and knowledge accumulation, and network building. However, avoid these things, and you open yourself up to all of the potential downsides of Freelancing: Lack of certainty and security, instability, no defined career path, painful business development. Hopefully, some of the above helps, but if you’re still unsure where to start, a good next step is to connect with professional freelancers on the Community section of this site. Find out first-hand how they go about building their business, ask them about specific elements of how to approach your career as an independent. The great thing about freelancers is they’re almost always willing to help each other so don’t be afraid of reaching out and asking for help!