7 minute read.

As freelancers and service professionals, we all struggle from time to time – whether it’s with getting work, getting organized, or getting paid. 

Real talk: This capitalist system isn’t designed for us freelancers. It’s rigged for wealthy corporatists who want to be wealthier. Creating unfair advantages is the name of the game. As a result, we solo freebirds are at a distinct disadvantage. 

We also often fall into the trap of wanting to be aggressively independent and do everything ourselves. This is neither sustainable nor realistic (especially considering that we cannot compete with corporations’ resources). 

While I cannot help you secure the resources of a greedy corporation, I can provide you with some guidance to effectively ask for support.

Note: If you’re looking for ways to support freelancers, I write about that here.

How to Get Past Feeling Like a Burden

If you’re like me, you might have a hangup when asking for help because you don’t want to feel like you’re burdening them. 

Consider that it’s much harder to gain advocates if you don’t advocate for yourself. And your business relies entirely on marketing yourself. 

The best kind of marketing is still by word-of-mouth.

That’s what a lot of effective marketing comes down to as a freelancer: talking to people about what you do. 

When people like you, they want to talk to other people about you. 

That doesn’t just apply to business; it also applies to your personal life.

Most people like to talk about people who have an impact on them—talking about someone you like, that you admire, and that you find compelling impacts your brain. It’s easy, it flows naturally, and it feels good. 

Family typically talks about you, friends will talk about you, and associates will talk about you, too. People you do not know could be talking about you, too, depending on your influence. 

Asking for Help is Human 

I used to really suck at asking for help because I thought it meant I was incapable of being an adult. That belief tied me to a false obligation to do things by myself, so I could prove I wasn’t a helpless child. And I suffered by drowning in stuff I desperately needed help with. 

Asking for help sucks because it’s vulnerable. It requires you to accept that you are not fully in control and need to rely on support outside yourself. 

But it’s human.

Nothing can truly be achieved alone. Humans need the support of others to succeed. 

We all need support from time to time. No one person has the solution to everything, so it makes more sense to depend on one another. We are a social species, after all. We share ideas and support so we can continue to exist. It’s wired into us.

Because the freelance business can feel so personal, it takes practice to diagnose problems and prescribe solutions. Aim to be candid about the help you need. 

Diagnose Problem, Prescribe Solution

Before asking for help, you need to do as much sleuthing on your own as possible. So put your diagnostic abilities to practice. What’s the issue? Are you struggling to find leads? Hard time landing clients? People not paying you on time? 

Once you nail down your problem, you can identify a solution. 

If it’s leads you need, you need more people talking you up and referring to you. If you’re struggling to land clients, you need more compelling offers. If you’re not getting paid on time (or at all), you need to revise your payment terms.

Are you not sure what the right solution to your problem is? 

Well, that makes your ask very simple: you need advice. 

I strongly recommend brainstorming solutions with someone you trust and who has relevant experience in your network. Find yourself some trusted advisors or a mentor. 

Note: I do not recommend asking family for business advice. Even if they are in business themselves, the family relationship can muddy the waters and be more of a hindrance than actual help.

Once you have a solution, you can decide what support you need. 

What Do You Ask For? 

It depends entirely on your situation. People are the most likely to help you when your requests are as specific as possible. The better you understand what you need, the easier it becomes to ask.

When formulating a request, try to have all of the following worked out:

• WHAT do you actually want? 

• From WHO? 

• By WHEN, or on what timeline, do you need it?

• HOW will you know you have been helped? What does that look like? 

Remember, you want to be as specific as possible. 

When I more regularly attended networking meetings, I witnessed folks get up and make some of the vaguest requests. IE. “If you know anyone who needs financial planning help, send them my way,” or “I’m looking for young people who want their first job.” 

These requests may sound specific at first, but do they really inspire you to think of a particular person? Doubtful. Lots of people need financial planning help. Lots of young people are looking for their first job. The goal here is to paint the most accurate picture of the person or business you want to be connected with. The clearer that picture, the easier it is to act on. 

If that picture is unclear to you, you need to go back to the drawing table before you make the ask.

So let’s say I am struggling with leads (which I do, from time to time). Let’s drill down further into this request. 

• WHAT: I want leads to startups or small business owners who want help developing their English-written brand content. I would like to receive these leads as introductions.

• WHO: I want to receive these leads from trusted colleagues familiar with me and my work and are willing to talk me up enthusiastically. 

• WHEN: I would like to receive these introductions within the next month.

• HOW: I will know that I have been helped when I receive a minimum of three introductions to folks who are interested in possibly hiring me to help them. 

I want to clarify that leads and clients are not the only asks you can make of your network. They are certainly some of the most effective asks for filling up your pipeline, but they are not the only means to support you.

Consider these other asks:

• Testimonials for your website, Google, Facebook, LinkedIn, etc. 

• Donations to your coffee fund – Many of us do creative work, and it’s perfectly acceptable to ask for tips. 

• Introductions to people who may provide avenues to opportunity

• For family and friends to pay full rates – Those closest to us often want or even expect discounted or free work from us. We are not obligated to work for free, especially when struggling.

Who Do You Ask? 

Most people won’t be able to support you directly, but each person has a network of people they know and speak to, and in their networks, those people might know others who could need your services – either now or in the future. 

Relationship building is a long game. It doesn’t typically yield immediate jobs, but the stronger the rapport you build with people who have deep and trusting networks, the more likely it is to create a pipeline of consistent referrals. 

I know; that’s not what you want to hear when you need work now. But relationships are essential for more than just business. You should be investing your time and energy into people regardless. 

If you’re unsure where to start with relationship building, start by asking: how can I support you? It’s a simple but powerful question.

Always Give Them the Chance to Opt-Out

Look, nobody likes feeling obligated to fulfill an ask. You don’t want anyone to act on an ask from you begrudgingly. It sours the relationship. It makes things awkward. It makes people feel used, especially when you ask someone who is not skilled at setting healthy boundaries.

I have been on the receiving end of requests that I agreed to begrudgingly far more times than I care to admit (I used to be one of those people pleasers who was shitty at boundary setting). The one thing these requests had in common was that I just didn’t feel like I could say no. 

So when you’re making your ask, you need to frame “no” as an acceptable option. Here are some tips for doing so:

• Qualify the request with “if you have the time” or “if you are able”

• Provide as much information as possible

• Do not attempt to tug on heartstrings and guilt the person into helping you

We are in an era of learning to revere consent. This doesn’t apply to just sex and intimacy. It applies to all human boundaries. If someone says “no” to your ask – that’s it. You have your answer. Time to say thank you and move on.

If you struggle with rejection, I recommend reading Rejection Proof by Jia Jiang. Jiang says, “Rejection is a human interaction with two sides. It often says more about the rejector than the rejectee and should never be used as the universal truth and sole judgment of merit.”

Remember, even if someone can’t help you right now, they might be able to help you later. That’s why properly framing your ask is so important. Manipulative framing will discourage people from helping you later, even if they can.

Be Patient, It Takes Practice

I sucked at all of this when I first started. I’m still practicing and improving, as it’s an ongoing process. 

I had terrible Impostor Syndrome (sometimes it still creeps in). My advice to you? Fight it. It’s worth fighting.

Asking for help is a skill. The more you practice, the better you’ll get.