Getting Help Is Hard But Here Are 4 Ways To Make It Easier

Jun 3, 2021 | Culture, Growth, Mindset & Identity

Entrepreneurship sure can be lonely.

We put a lot of pressure on ourselves to go it alone, figure it out ourselves, and generally handle it.

Getting help—whether that looks like building a team, plugging into a support community, or partnering up with someone else—often goes against the rugged individualism we were trained to aspire to.

Asking for support, even from someone you’re paying, can bring up all sorts of insecurities. Shouldn’t I have this figured out by now? What if they think I’m not good enough?

Intellectually, we know we need help.

But acting on that need is a whole other ballgame.

Today, I’d like to take a closer look at why we feel compelled to go it alone and offer 4 things you can do to make asking for support or hiring help a little easier.

Rugged individualism isn’t all it’s cracked up to be.

One of the defining moral structures of white American culture is rugged individualism. And while lots of other countries and communities have cultures that are defined by more collective values, the default language of business draws heavily on American individualism. We’re really good at exporting values that don’t serve us particularly well.

Many of us have grown up being taught self-reliance and independence—and how those qualities are tied to our value to society. Taking care of yourself by yourself has become a moral virtue. Relying on others has become a moral ill.

At the root of this is the American obsession with self-reliance, which makes it more acceptable to applaud an individual for working himself to death than to argue that an individual working himself to death is evidence of a flawed economic system.
— Jia Tolentino, The Gig Economy Celebrates Working Yourself To Death

Rugged individualism has taught us to disconnect ourselves from others so that we can prove we’re good enough all on our own. By not seeking collaborative or collective solutions, we make it easier for others to see us as highly capable and valuable to society.

This cultural attitude took form as white Americans colonized the west. There were few institutional or governmental systems to provide support for their conquest and subsequent homesteading. As the colonizers crossed the Mississippi River and pushed out into the Great Plains, they destroyed the indigenous communities that valued collective, mutually reliant life and replaced it with an every-man-for-himself system of values.

The first known use of the term was in a speech by Herbert Hoover, the president that presided over—probably not coincidentally—the economic collapse that brought on The Great Depression,  He used “rugged individualism” to contrast the American society with the culture and governing philosophy of Europe.

Ronald Reagan used the spirit of rugged individualism to turn us against and dismantle the institutions that had led to wider spread prosperity. Margaret Thatcher set about similar changes in the UK. 

This isn’t making us very happy…

The spirit of rugged individualism—first conceived in the violent conquest of the American west—shapes how we see our problems, challenges, and opportunities today. Johann Hari, the author of Lost Connectionscites research that ties how difficult it is to make yourself happier in the US in this Vox interview:

We have an instinctively individualistic definition of what happiness means; many other cultures have an instinctively collectivist definition of what happiness means. And it turns out individualism just doesn’t work very well — we’re not that species.

Okay, so rugged individualism contributes to our pathological loneliness, our economic instability as individuals and as a society, and our struggles with happiness.

It seems like it’s past time to do things a bit differently, eh?

Why is it still so hard to ask for help?

The reason I bring up rugged individualism and its ill effects is that it’s an important framework for making sense of the conflict between knowing that getting help is key to being happier or more satisfied and continually avoiding asking for help.

It’s not enough to take some management training, get better at delegating, or writing a compelling job description if you don’t simultaneously shift your posture toward having others help you build your dream. It’s not enough to practice scripts for asking for help, join a mastermind group, or frequent a support community if you don’t work at breaking down the belief that asking for help means you’re not good enough on your own.

And similarly, if we’re in the positioning of offering support—as a coach, a community builder, a service provider, etc—not dismantling our ingrained individualism can create a harmful relationship or group dynamic that makes it hard for people to get the support they need.

Operating in this way—constantly re-inscribing the same standards that make life so un-neededly hard—is psychologically [fracked]. But it’s also just flat-out exhausting.
— Anne Helen Petersen, Can’t Even

With that all out of the way, let’s look at 4 concrete ways you can prepare to ask for and receive support—whether from team members, peers, or mentors—as a small business owner.

1. Define Your Needs

If you’re like me, you don’t slow down to even consider what needs you have that aren’t being met or satisfied. Maybe you feel confused, tired, frustrated, or stuck and you just don’t know why.

There isn’t a specific problem to solve and there isn’t a question you can’t answer. But you still don’t feel like you’re thriving.

Many of us have been socialized to repress our needs and, instead, function for other people’s needs. Yep, that’s rugged individualism at work. But it’s also a variety of other forces that capitalism, misogyny, ableism, and white supremacism employ to keep us in our place or make us more productive cogs in the machine.

Often, we can identify the bad feelings but we have a hard time identifying what we need to resolve or process them. Therefore, getting specific about what we need is a key component of asking for and then receiving support.

You can use a needs inventory like this one or Liz Wiltsie has a whole program on naming & expressing your needs at work.

Once you’ve named the need, then you can consider who may be able to support you in filling that need and how you might request that support.

2. Establish a relationship

It’s near impossible to receive genuine support from someone you’re not in relationship with. You can receive instructions, you can receive knowledge, and you can also receive useless advice. But support? Not really.

Establishing a relationship doesn’t have to be a long, drawn-out affair.

Joining a niche community (this one!) often means crossing a boundary into a group of people with shared experiences and shared values—which can act as a shortcut for establishing a relationship and receiving genuine support.

Hiring someone and leading them through a thoughtful onboarding process establishes a mutually beneficial relationship.

Inviting someone to join you for coffee (virtual or otherwise) and giving a specific container or purpose to your meet-up can establish a relationship.

Sure, any of these types of relationships can grow into so much more. But once you’ve established a relationship, you have a clearer expectation of what kinds of support you can request and what boundaries you might need to put in place to receive that support.

3. Respect Your Capacity

My excess psychological and emotional capacity—or lack thereof—is directly tied to the kind of support I can request and receive.

When I have a little more capacity at my disposal, I might be open to brainstorming or processing a new idea with a team member.

But no matter how helpful those activities might be on a good day, if I don’t have the capacity, brainstorming and collaborative processing will send me into a downward spiral. For me, those activities require a lot of energy and concentration because verbal processing (both listening and speaking) is difficult for me.

On the other hand, even on a bad day, I might have the capacity to request and receive help in writing—the form of communication that comes most easily to me.

Your capacity ups & downs might affect you completely differently. Some will always have the capacity for a one-on-one conversation. Others might prefer to request book or podcast recommendations and spend a day doing research. Some prefer to receive open-ended coaching questions when they’re stuck and others want to hear stories.

As you pay more attention to your capacity and how it impacts your ability to request & receive support, you can find ways to structure your work and responsibilities so that you do have the capacity for the heavier lift forms of support that you find really helpful.

For instance, I save Fridays as a “buffer” day because those start out with our weekly team meeting. These meetings can be incredibly productive and I often move projects forward as I discuss them with Shannon—but the most productive of these meetings absolutely wreck me because I’m doing a heavy lift with my remaining capacity. So I rarely plan anything specific to do on Friday afternoons. And sometimes, I just have to be honest and say, “I don’t have the capacity for this kind of conversation today.”

4. Release Your Ownership

At some point last year, leadership coach and flower farmer Julie Treanor related that every time we voice an idea, we give up ownership of it. It’s not ours anymore, it belongs to everyone we’re involving in the process of making it real.

(I’m grossly paraphrasing what she said, but I’m pretty sure that was the gist of it!)

Releasing our ownership is some of the hardest work of asking for and receiving support.

With your team, that means being willing to truly collaborate on a project—instead of just delegating. It also means allowing someone else to bring their version of an email, a project, or a system to fruition—knowing and celebrating that it’s not the same as your version.

With your peers, it means being willing to ask questions or pose challenges and releasing your ownership of the solution. It means being willing to be misunderstood at first so that you can eventually be understood and get what you need.

With a coach or a service provider, it means letting them take the wheel and set the course to follow. It means trusting the process and letting go of expectations of how things are “supposed” to work.

There are many things that make requesting and receiving support a challenge. But if you find yourself on the verge of reaching out and still having a hard time making it happen, as yourself how you might still be looking to own the result or control the outcome.

Get clear on why that’s stopping you up and then look for guardrails you might be able to put in place to allow you to release your need for ownership.

You deserve support.

You don’t have to earn the right to camaraderie. You don’t have to prove yourself to be worthy of building a team to realize your vision. You don’t have to justify your need to know that you’re not the only one to experience this high or that low.

Others deserve support, too. And while this article focused on how you can set yourself up to receive support, it’s really about shifting to a culture of care and interdependence.

The more we lean on our interconnectedness—as opposed to individualism—the more we can create mutually beneficial systems of help and care.

I believe that most of the roadblocks in the way of requesting and receiving support are cultural and systemic. But you don’t have to wait for a sweeping change in societal values to feel like you’re not alone.

Whether it’s time to hire, find peer support, or invest in specialized support for your business, it’s worth doing the individual work to team up.


This month inside The What Works Network, we’re deep-diving into the ways we can “team-up” to build stronger businesses.

We’ll take a look at hiring and managing, as well as requesting emotional support, building the right support structures for yourself, and moving beyond an individualistic framing of goals.

On June 24, we’re gathering live for the Team Up virtual conference where we’ll talk about leadership, networking, working together, and setting up your business to work without you.

To get in on this deep dive and get members-only access to our virtual conference, join The What Works Network today.

Host of What Works

Tara is a podcaster, small business community leader, strategist, and speaker. She’s been helping small business owners build stronger businesses for over a decade.  

Tara McMullin, What Works Weekly Newsletter

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