One of the questions I’ve been getting often since running Offbeat has nothing to do with L&D. It’s more along the lines of “how did you get to building your own thing?” I’ve been wanting to address this for a while, but I wasn’t ready to do it. I also wasn’t sure how to frame it. Because I didn’t want to talk about general entrepreneurship advice, but rather about the journey of a former internal L&D jumping to build my own business. While some general advice might be worth pursuing, operating in the learning and development industry isn’t the same as building something in product, marketing, or sales.

While I have plenty of thoughts to share from my last 4 and a half years of running Offbeat full-time, I’m well aware that I’m one person, based in Romania, serving L&D professionals. I knew other people from other countries, serving other audiences, doing coaching or training, might have different experiences. So I wanted to spend some time getting to know how others see their entrepreneurship and freelancing journeys before putting pen to paper, or better said, fingers to keyboard.

This piece is for anyone who’s actively thinking about going freelance, those who are doing it but have never spoken to others, and those who have no plans to do so, but are wondering what the grass looks like on the other side of the fence. It’s about my experience, but also about the journeys of eight more people I interviewed, and some others I’ve watched closely. It speaks about the technicalities, but also about the emotional journey of running your own show.

Deciding to go freelance — intentional or not?

I’ve always wanted to build something of my own. I don’t know exactly where I first got the idea, because nobody in my family had been an entrepreneur up until a few years back. It was just a desire to see something happen from nothing. So even before Offbeat, I had been actively pursuing small experiments alongside my full-time role. None of them ever led anywhere. Until 2020, when I started a series of LinkedIn posts that led to what today we call Offbeat.

Most of the people I interviewed had explored the idea of entrepreneurship as a path for them. Jess Almlie thought it would be something she’d do before she retires. Klara Hermesz bought a domain years before quitting. But haven’t we all thought about it at some point? Millennials and Gen Zs grew up with what Chris Wong calls a “romanticized view of working for yourself,” with stories of successful founders and following influencers who seem to have the freedom all of us think we want.

When put in front of the decision to go freelance, though, most of us get antsy. I know I did. It took me months to decide whether I would actually do it or not. I remember telling my then manager that I’m quitting and spending months wondering, “What the hell am I doing, leaving a good job, a nice team, and a steady paycheck behind to pursue a dream?”

Lo and behold, that’s not everyone’s story. Quite a few of those I interviewed came face to face with the decision of going freelance after they lost their job during layoffs or when their employer decided to do some restructuring. When faced with that situation, Liam Moore started looking for a new role. But after becoming disillusioned with the job market, he decided to do some coaching as interim work until he found another role. Slowly, he gave up on the idea of ever going in-house again, and focused on building his coaching and supervision practice. After an acquisition, Jess found herself offered a role she didn’t particularly enjoy, so she went on interviewing for other companies. In some cases, she didn’t get through to getting the job, while in others she decided it would be better to step out of the recruitment process when she better understood what she would be dealing with. After a while, she took time to workshop her options on her own, answered all the career questions she could find online, and upon reflection she realized her next step wasn’t going to be another corporate role.

Regardless of what triggered the decision, the main thing that kept everyone up at night was, unsurprisingly, the financial pressure. Some jumped into the journey with some sort of financial cushion from savings or a severance. Others, like those I spoke to from the US, had to think about health insurance as well (health coverage in the US comes through an employer). Many had serious conversations with their partners and spouses, and even consulted financial advisors. 

Tom McDowall, who started his journey with Evolve in 2018, is the only one who had a slightly different view of the financial pressures you deal with at the beginning of such a journey. Out of all the peers I spoke with, he’s the only one who took this seriously pre-2020, when things were looking slightly different, and demand for services in L&D was higher. But even he mentioned that having a 6-month financial cushion today is important, given times have changed.

The advice that stood out to me came from Jess Almlie. Regardless of your path of choice, networking and putting yourself out there as early as you can is an important contributor to a later decision. Being part of communities like Offbeat or L&D Shakers, posting on LinkedIn or Substack, and joining local or online events brings you support for your current role, but can also lower the pressure later on if you decide to go freelance. Jess started her newsletter and posting regularly on LinkedIn about a year or so before starting her business. I ran Offbeat for almost two years before quitting my job. While none of it guarantees any success, it can make the landing smoother.

Mayday, mayday, the start is more confusing than expected

It’s your first Monday working full-time as a freelancer. What should you do? Build a website? Do outreach? Figure out your offering? Figure out your taxes? All of the above? Something else?

The answer is never straightforward because it all depends on what your previous efforts have looked like. Offbeat was already incorporated, I had an accountant, and had a steady presence on LinkedIn when I first started working on my own. Truth be told, I can’t even fully remember what my focus was at first, but my guess is that I started thinking about our offering. I was relatively clear about the problem we were trying to solve, which was that L&D teams are not being relevant in their organizations, but I was still unclear about what our solution was. Four years in, people are still unsure about what we do at Offbeat, so we still have a lot of work to do to clarify our offering.

But something Klara mentioned stayed with me. Something she feels she got wrong at first was that she “started with what I wanted to do instead of what anyone needed. I wanted to help companies build learning cultures. It's a lovely idea. Almost nobody will pay for it, or at least not enough companies to build a business on.” The positive side of the story is that she didn’t stay attached to the idea for long. She offered a free week of consulting, piloted a few workshop ideas, and paid attention to what people actually responded to. None of it pointed back to learning cultures. It pointed to AI adoption, something she was already investigating herself, and what she ended up doing after all.

A lot of the work you’ll have to do at first will be figuring out what exactly you will be paid for. While it would be fantastic for the process to be one and done, the reality is messier and way longer. What one client will pay for might not be the same as what another client is willing to invest in. In L&D, we usually come with a range of possibilities. We can run training or consult on various areas like leadership development, onboarding, succession planning, or learning experience design, among others. We can do coaching if we’re certified. We can facilitate. We can create e-learning. We can support AI transformation. And we can even plan events. Deciding what our services will be is a combination of what our skill set is, but also, just like Klara mentioned, what the market is willing to pay for. If the two converge to be something you also enjoy, that’s fantastic, though not always the case. 

Not enjoying the work is a big risk for anyone who will start freelancing in L&D. When you’re just starting out, you might not get the most glamorous projects, so there’s a real chance you’ll quickly burn out. Paired with the fact that figuring out what companies can pay for takes time, the initial weeks can feel confusing and overwhelming.

Oftentimes, to counter that confusion, we fill our time with something we can control, like building a portfolio or designing our website. Tom McDowall mentions this is the advice everyone hates, but he truly doesn’t believe this is where the focus of a new freelancer should be. Dwayne Britton brought up a similar point. Having been part of organizations where beautifully designed assets were a must, he also felt pressured at first to spend a lot of time designing his website, only to later realize there are better things to do. Jess Almlie built a one-pager in Wix herself, without putting too much pressure on it. It took her more than a year before she felt the need to invest in something more professional.

My own experience says that clarity is the most important point of any marketing asset you’ll build. When you’re not sure whether what you offer will actually make money, you’ll lose time designing and redesigning your beautiful website or portfolio. And that time can be spent in better ways.

What most people agree on is that time is well spent when you’re talking to potential clients. 

Getting clients — from your network and beyond

Sales was never my thing. To this day, it still isn’t. Even before Offbeat, I knew this would be the bane of my existence. I’ve always had a definition of sales that involved a lot of outreach, trying to convince people my services and products were the best positioned and priced to solve their problems, being a bit pushy, following up on emails nobody ever read, and being rejected over and over and over again. Tom calls the whole process “icky”, while Klara acknowledges that she would ignore the same “send follow-up” task for weeks. Lack of time wasn’t her problem, but “a fear of being the person who sells”.

Working in L&D rarely prepares you to sell. Sure, you might be pitching ideas to your stakeholders. You might negotiate contracts. You might be managing budgets. But doing so on your own, when your end-of-the-month paycheck depends on whether you get a client or not, brings up an emotional pressure we rarely talk about. If you’re not naturally someone who enjoys sales, you’ll most likely face that pressure. I found that the best thing you can do is acknowledge it and do the work you need to do in spite of it.

A few of the people I interviewed, like Tom and Dwayne, found their first clients in their existing network. I have even heard of former L&D professionals who went freelance and turned their former employers into their first clients. But if that’s not something you can do, building a strong network even before going freelance is a path to your first clients when you take the leap. This doesn’t mean you won’t need to specifically ask or sell, but it might make the process easier.

Your network can also give you opportunities to speak in front of potential clients. Tom and Chris both mentioned they got clients from speaking opportunities, while Rafize Santos mentioned this is part of her commercial strategy. On the other hand, Jess signals that, for her, the free time she gave away in speaking gigs never turned into paid work. My experience is very similar. Regardless, this could be a path for when your network eventually dries up, and you need to expand who sees your work. 

The other one is, of course, cold outreach. While this isn’t an uncommon tactic, most of those I interviewed didn’t report a lot of success from the process. A piece of advice that stayed with me, though, comes from Laura Massetti, “Cold outreach works when the targeting is surgical. Loose targeting at volume mostly burns your capacity while making you feel productive."

In hindsight, I think regardless of the path you choose, sales outreach or inbound marketing, your offering and target audience need to be relatively clear. You also need to be prepared to build relationships before selling. In most cases, sales cycles for coaching, training, facilitation, and learning design services aren’t short. Budgets in L&D and HR teams (where we usually pull our revenue from) are also in constant flux these days. Building strong relationships and being clear on what you offer increases the likelihood of getting a call or email when the time is right.

Strong relationships also help you get referred. Quite a few of those I interviewed mentioned referrals as a sales stream. Running an L&D community and being a part of many others, I can see how people ask for referrals. I can also see that sometimes freelancers are aggressive in making their case, which is a behavior I don’t personally appreciate in a community. I think giving value in a community as a member will increase your chances of being spotted when a potential client is searching for your services. It doesn’t mean you shouldn’t tell people you can help them if they ask for recommendations, but there’s a fine line between being pushy and being helpful, and we all need to learn how to walk it.

Because she knew sales wasn’t her strong suit, Rafize chose to hire a commercial consultant/ mentor as her first move in the business. She calls it the best investment she made. I think this is an interesting thing to consider.

Navigating the tumultuous waters of pricing

Next to figuring out offerings and sales, pricing has been reported by those I interviewed as "one of the most difficult pieces." Jess quoted two companies the same price for the same service. One said, "There's no way we can pay that." The other signed without blinking. I often found myself in the position to run more-or-less the same service for two different companies, at two very different prices. If you operate locally, budgets or how much “pull” an L&D team has can influence how much companies can pay you. If you operate globally, as Offbeat does, geography makes things even more difficult.

An interesting exercise you can do is something Chris tried himself. Ask around your network what others charge for the same or similar services. Or if you had an internal role previously, refer to the budget you had available. 

Even so, don’t expect pricing to be a one-and-done job either. Jess’s and my experience with two different clients paying different prices or choosing to pay or not for the same services is one side of the story. The other side is market changes and the perceived value of the service.

The economy hasn’t been particularly stable over the past few years, and what companies perceive as useful has also shifted quite a lot. Four years ago, supporting AI adoption wasn’t even a thing. Today, it’s probably the most sought-after service. Leadership development was always big, but even this budget line took a dip in the past few years. Staying in touch with market trends and trying to learn where money is actually spent is the best way to navigate murky waters.

If you’re a new freelancer with no experience in sales, there’s also a high chance you’ll set prices that are too low. There’s an entire conversation over whether that’s a good idea or not. Some say it’s a good strategy, because it allows you to win clients simply because your services are cheaper. Others say it’s a bad one, because it might position your services as “lower quality.” I’m not an expert in pricing, and I think that as long as you’re able to justify your choices, no decision is wrong.

Keeping a cash flow, a P&L, being hyper-aware of your costs, including your taxes, and the offers you made that were accepted or rejected, are all good, healthy practices for any business.

The emotional ups and downs

How one navigates entrepreneurship or freelancing emotionally depends on many things. I know I wasn't ready for it. Although I could've definitely asked others what their journey was, I also think nothing truly prepares you for it. A few months back, I was talking to someone running a similar company to Offbeat, but for People Professionals, and our conclusion was interesting. If you look on LinkedIn, it seems like everyone is having a blast and doing tons of things. Behind the scenes, though, the struggle is real. Things I wasn't prepared for:

• "Who am I to do this?"
• "What are they doing and we're not?"
• "Everyone around me is getting promoted or getting raises; I feel stuck."
• "I don't know what the right choice is."
• "Are our services truly worth it?"
• "We lost another customer. We must be doing something wrong."
• "Will we have enough money to pay our salaries?"
• "Am I a bad person when asking for money for this?"

These are just a few of the thoughts and questions I struggle with every day. In my first two years of running Offbeat full-time, I let these thoughts overwhelm me. I ended up doing nothing else but Offbeat, putting on pause almost everything else in my life, including friendships and myself. I quickly learned that working 17-hour days, taking no holidays, or working while on the few days I "take off" isn't sustainable or healthy. So I now push myself to remember who I am outside work, and I'm actively working on recreating identities that have nothing to do with Offbeat.

Both myself, and my co-founder, Ioana, like all those I interviewed, choose to wake up every day and do this not because it's easy, but because we believe it can lead to something better both for ourselves and others. It doesn't mean the journey is smooth.

While I'm not saying this will happen to you, I wish someone would've honestly spoken to me about the low parts of being an entrepreneur. About the moments where there's no right or wrong decision, but you still need to choose a path, about the sleepless nights, the doubts, and the questions. I hope if you're doing this or you plan to, your journey is or will be easier.

Conclusions

The decision to become a freelancer/ entrepreneur isn’t an easy one. And I only just covered the idea of building a service business. Other options, like building a tech product, have other implications you need to consider. 

While I truly don’t believe you’re ever fully ready for it, I would advise you to talk to as many people as possible as early as you can. Ask about the technical bits, but also about the emotional journey. Having done this for more than 4 years, I truly believe entrepreneurship is like running a marathon. The one thing that will be for sure in your way is your own brain. The technical stuff can always be learned, but how you navigate the emotional lows and highs is extremely important.

I’ll leave you now with additional words of wisdom I got from some of the people I interviewed:

• Klara Hermesz: "The bravest thing an introvert can do is become an entrepreneur."
• Rafize Santos: "Is it hard? Yes. Will it be worth it? Absolutely."
• Chris Wong: "Remember this: Try"
• Tom McDowall: "If you're bored, you're not working hard enough."
• Dwayne Britton: "Bet on you."