How to Make Working For Yourself Your Dream Job

When many people are asked what their "dream job" might be, the answer often involves becoming their own boss. It often doesn't matter in what field—the main allure is no longer having any superiors to answer to. In fact, according to one recent study, 29 million Americans are considering going independent in the near future. But it's a pretty fair bet that not all of them will.

That's understandable. There's no one formula that makes being independent work for everybody who tries it. But one of the trickiest hurdles is to translate your "dream job" notion of self-employment into a sustainable—and still personally satisfying—reality. Here's what that takes.

Perhaps the hardest lesson most independent workers learn is also one of the first that they face: That your "dream job," whatever it consists of, takes hard work to realize and usually isn't what you thought it would be once you've finally realized it.

You’ll have to overcome decision fatigue as you make choice after choice, often without much experience or information to go by. You’ll learn how to set priorities, and value and price your work. Plus—and perhaps most arresting of all—instead of one boss (yourself), you’ll actually have several, in the form of clients, each with their own requests. Paradoxically enough, having control over everything in your professional life can be thrilling and paralyzing at once. And after the initial euphoria of self-employment wears off, you may worry that you made a mistake.

The knowledge you acquired in order to become an expert in your field isn’t the same as the skills required of a business owner. Learning a whole new skill set is likely to make you feel incompetent. That can lead to self-doubt, which can tank your entire effort if you aren't careful. Bear in mind that this anxiety is normal and temporary.

Getting past it, though, takes recognizing that once you have settled into independent work, you probably won't describe it as your dream job—but you'll still enjoy it. Most independents find that after mastering the practical realities of working for themselves, they wouldn't trade it for anything.

Building a sustainable business doing exactly the kind of work you want to do takes time. Your first clients and projects may not be ideal. Give yourself plenty of financial runway. While reducing your debt is critical, having cash on hand is actually more important for independents. This might sound counterintuitive. Obviously, having no debt is ideal but isn’t always practical. Money in the bank makes you feel less desperate so you don’t have to take just any prospect that comes your way.

Soon after going solo, you may also find that you need to pay off debts at a slower rate than you'd like while building a solid financial base. Having cash reserves helps here, too. That helps you ride out the natural fluctuations you'll inevitably meet with in the early stages of business. This way you won't find yourself white-knuckling it with a carton of ice cream in one hand and the other furiously tapping your keyboard as you search the internet for a job.

Most aspiring solopreneurs' daydreams don’t feature the fact that everything—including bringing in revenue—rests squarely on our own shoulders. Selling is a new skill for most independents. It’s easy to rely on your existing contacts for those initial clients, but when the friend well runs dry, you may not know whether to go to events, adopt a content marketing strategy, start a blog, or all of the above.

Trying out an array of business-building methods for the first time can drain you. While there are some general recipes for business success, the specific strategies that work vary tremendously from person to person. So take time to think about what you naturally enjoy so you can apply those skills to the type of promotion you'll need to adopt.

This goes for other parts of your business, too. Know your strengths and put them to use—including in functions for which you may not have applied them yet. Then automate or outsource tasks you hate or just aren't good at, as well as scheduling, building a website, or writing copy as the case may be. Just because your business's success or failure is all on you doesn't mean that every single task needs to be done by your own two hands.

One of the biggest surprises for independents is finding ourselves sitting at home, unsure how to proceed.

Untethered for the first time, and having to create all the rules from scratch, can be disorienting. You may begin to realize how much of your career and work style has actually been dictated by someone else. Many of the norms of 9-to-5 work are vestiges of the Industrial Revolution, and reflect the exigencies of factory management more than those of 21st-century knowledge work. The work habits you've fallen into may not serve you so well when you've dramatically changed the context in which you're applying them.

To adjust to being taken off autopilot for the first time, keep asking yourself these four questions. It's okay if the answers change over time—the key is to gradually get reacquainted with the new, self-employed you:

  1. Are you best in tiny bursts throughout the day or long stretches that begin at a certain time of day?
  2. Do you work best in total silence or amid the hum in a coffee shop?
  3. Do you need to go into an office, or are you disciplined enough to avoid distractions at home?
  4. What depletes your energy?

Finally, don’t be disillusioned if working for yourself doesn’t look exactly as you expected. We tend to build up our "dream jobs" to such a degree that some measure of disappointment may be inevitable. But it doesn't have to do you in.

Once you understand your main assets and how to get the best out of yourself, your work will come pretty darn close to the stuff of your dreams—and way better than wishing for a different life.

A version of this article, A Brutally Realistic Guide To Your "Dream Job" Of Working For Yourself, originally appeared on Fast Company.

A Framework for Evaluating Speaking, Podcast & Guest Post Opportunities

I wonder if you have any pointers on how to think about requests like the one below. I need a better framework in general for thinking about this stuff.

In the past it would have been an automatic “yes”. Arguably, it’s potential exposure to a new audience. On the flip side, it’s them using my name to get cred and/or eyeballs. I don’t even know how to objectively evaluate who is getting the better end of the deal. I guess on the third hand it could be an “in” for future collaborations.

I’d really appreciate your perspective. Thank you!

I received this email Avdi Grimm, author of several books and the creator of Ruby Tapas. He received a request for an on-camera interview while attending a conference. Given his limited time and a need to meet up with colleagues, opportunity cost was high.

It's a common question so I thought I'd share my framework for whether an opportunity to share your expertise for free is really worth it.

Everyone loves to talk about exposure.

Let me be a bit more precise. People who are trying to entice you to give them more page views tout exposure or bolster their program, over-emphasize it. But will more exposure really help? Should you ignore opportunity cost or forgo short-term income for the promise of long-term gain?

The answer is…it depends. The lure of exposure can absolutely just be bait to lure you in. But the right exposure, at the right place, at the right moment can give much needed momentum. That’s what makes it so tricky.

How do you know when an opportunity is simply bait vs a career changer?

My framework has two parts. The first part, Why Exposure Might Be Worth It, focuses your internal motivations. The second, the Exposure Checklist, focuses on the external aspects of an opportunity.

Why Exposure Might Be Worth It

Other exposure opportunities are a bit murkier. While you may not get new clients as a result, guest blogging, speaking and being interviewed on a podcast can all be fantastic ways of making new audience aware of you. 

I’m not suggesting you take every opportunity. When just getting started, you might decide to take just about any outlet that offers. Once you’ve gained a bigger foothold with your intended audience, be more selective about the invitations you accept.

Before agreeing to do something for exposure only, you need to carefully consider what you want to get out of it. Knowing what you want out of an interview, guest blog post, speaking gig or podcast can mean the difference between an aimless waste of time and one that helps you achieve important business goals.

New Audiences. 

Expanding your audience is critical when you’re launching a business or product. This might be a good reason you’d be open to exposure.  Posting on your Twitter feed, Facebook page or on your blog often reaches the same audience over and over again. If you want to sell more products, you’re going to need reach new people. 


This is especially good for speaking or podcast opportunities. If you have a new book coming out but you haven’t talked about the material publicly much yet, you may want to take an interview at a smaller outlet to give you a chance to practice your talking points. This will help you figure out the pull quotes (i.e. phrases or quotes that can be used in articles, or on social media). It can also help you understand what most resonates with your audience.

Future Collaboration.

Partnering with like-minded people and companies can be great for your brand — and your business. A few hours of your time is worth it for a company that’s a perfect fit, sending leads your way.

A real life example.

I’m in the midst of writing a series of books so I’m open to new audiences. When asked to be on personal profitability podcast for people who have side projects, I said yes to practice and because it was a new audience. I also wrote an article for Fast Company which ended up being shared 5,000 times. The opportunity cost for writing that piece was well worth it. 

Whatever your reasons are for speaking, taking an interview, doing a podcast or writing a guest post, make sure you're clear about why you're doing it. If you don’t have a good reason, question why you accepted the opportunity. It might be an ego thing or an inability to say no.

Taking every opportunity willy nilly can also indicate a lack of understanding about who you serve, how you solve their problem and how you're different. This is known as positioning. When you're clear about your position, it's easy to name prospects, podcasts, publications or conferences that are a good fit. If you're not clear about your positioning, all the exposure in the world isn't going to make a difference. When it comes to opportunities for exposure, alignment is everything.

Exposure Checklist

Here are 7 things to look at when considering an opportunity.

1. Audience

Even if an outlet has a reach of a million, if the audience isn’t a good fit, don’t waste your time. If they don’t mention their audience in their invitation, be sure to ask before accepting unless you already know the outlet. You might accept an opportunity if you're looking to expand and the outlet is adjacent to your core audience. For example, if you work primarily with rubyists but would like to branch out to agile development, going on a polyglot podcast might be worthwhile. Going after adjacent audiences is a bit trickier so be sure can articulate why it's a good fit.

2. Topic

What is the topic? Does it align well with your work?

If not, those new eyeballs aren’t going to do a thing for you. Instead, spend your time writing an article for someone else or find another conference to speak on a topic aligned with your audience. If going on a podcast or asked to be interviewed on video, be sure to find out what questions are they planning to ask. This last question is critical to 1) ensure the interview is a good fit 2) help you prepare your thoughts.

3. Reach

Reach simply means how many eyeballs (or ears) you might expect to get from the opportunity. If it doesn’t pass the reach test, it means that they’re likely to get more from the interaction that you will. Generally, you’ll likely want to turn it down in favor of something that has a broader reach. You may also consider smaller sites with a more niched audience that aligns with your own. Again, this goes back to your strategy. 

4. Reputation

When you appear on a podcast, promotional video or on a blog, you become associated with that brand. It takes a long time and bunch of hard work to change your online reputation once it's been sullied so be sure that the outlet has a good reputation. Reputation is often subjective so base your reputation guidelines on your values and comfort with things like  sensationalistic sites or provocative ones where clickbait is the rule. When it comes to conferences, things like a Code of Conduct and past speakers may fall under consideration.

5. Promotion

"Editors will tell you anything to get you to give them to give you something for free. Even if their audience is 2 million, if the editor is lazy in their promotion, only 2,000 people might actually see your piece." says Kathryn Brown, a former editor of a high volume publication.

When considering an outlet Brown suggests asking the editor about their plan to promote you. Will they tweet about you once? Multiple times? Will you be in their newsletter? Will they link to you? Will they promote you at all? A site with a million views will do you no good if they’re stingy with their promotion. 

6. Review Rights

Ideally you want approval over what they publish (video, audio or writing) to make sure your thoughts are in proper context. Having a review may also be important if you tend to talk off the cuff or are worried they’ll distort your meaning in the editing process. When speaking, be sure to know if your talk will be recorded. Having the ability to approve your content might be important in some cases but less important for others. This is something you need to decide for yourself.

7. Opportunity Cost

Time is your most important commodity. For everything you say yes to, you’re saying no to something else. An hour may not seem like a lot of time to give but it might mean you say no to talking with a prospect or putting that time towards creating your product. Opportunity costs also include intangibles like energy. When so many opportunities seem ripe with potential, it can be really hard to say no. However, saying yes too often can lead to an overcrowded schedule, slipping deadlines or even burnout with little to show for your effort.

A Final Check.

Your gut. After you've thought through everything, doing a final gut check provides balance to the analytical checklist. Never say yes to an opportunity in exchange for wider acclaim when your heart says no. Ignoring your gut can set you on the path to resentment. Save yourself the pain and just say no.

Quick Exposure Checklist:

  • What do I want to get from this?
  • Is this my audience?
  • Is the topic something my audience cares about?
  • How big a reach does the outlet have?
  • Does associating with this outlet enhance or bring my brand down?
  • Will I have a chance to review the content?
  • What does my gut say?

If you can't answer the questions in the checklist, you have a bigger problem. You don't understand who, what and why well enough.  Clarity on your positioning is paramount. I plan to go into more depth about this in the future. But if you want to dig in now, check out Philip Morgan's Positioning Crash Course.

If you have a book, app or services to sell, chances are you need this kind exposure speaking, podcasts, and guest blogging offers. Have a list of dreams publications, podcasts and conferences. Don't wait for them to come to you--approach them. That way you're in charge of your exposure -- and how you promote yourself.

When to Quit Your Day Job

There are plenty of people on the internet imploring you to “quit your day job and follow your passion!” so you can have the life you want. They’ll tell you how they did it. How they earned 20k in one month. Now they have a fabulous life traveling the world without a care in the world. You can do it too!

This is some good old fashioned marketing bullshit.

Mostly, it’s candy-coated shit.

These freelancing cheerleaders are showing you the glossy side of things. Underneath those pretty pictures they paint are harder realities. Trying to get wifi in their hut in a remote location. The years of hard work they put in working for crappy clients. How they made very little pay for years on end.

Yes, honoring your values is important, critical even. Having the flexibility for the life you want is absolutely a solid reason for working for yourself. It’s just that, well, starting a business isn’t as easy as 1-2-3…fabulous life! 

It's true that some can start out making great money right away, particularly high in-demand folks like software developers. Others have to work much harder to build a sustainable and highly profitable clientele. Even for the former, it takes time to get the work you really want or making enough money from products to support you.  Sometimes your business is just a side gig to a day job. Even if you do work for yourself, in the early days it can still feel like having a day job.

I don’t want to dissuade you from working for yourself.

I’m just not one to varnish something up, sell you something that’s unobtainable or unrealistic. I want you to have the career freedom you seek. I know you can have it.

I could tell you to quit your day job tomorrow. I could tell you just believe that you'll get clients, that you'll build wings on the way down, float back, and be sitting on the beach sipping that umbrella drink while casually looking at your laptop.

You'd probably like me better. But most of you wouldn't find those magical wings sitting next to that fruity drink poolside. You might even end up like my colleagues who quit their day jobs the day after taking a coaching course, emboldened by the idea that they could "have the life they want!" tomorrow. Six months later, everyone who quit their day job to start a business was back in a full-time job, resigned to working for someone else the remainder of their career. Only one of them was still building her business — while working part-time. These failed business owners always stuck with me.

I don't want you to be one of them.

And you don't have to be. Knowing when to build on the side and when quit your day job can be tricky. Here’s a real world story about how a woman went from career beginning, to having a side gig to having the business she really wanted. 


It was the middle of a downturn. Jenni had just graduated from journalism school. Given the economy and state of her career, Jenni took a job writing for Construction & Demolition Debris Recycling Magazine. Hardly what she imagined when she dreamed of being a writer.

Even though she had zero interest in the topic, she saw the job as a good chance to learn, the work was fun and challenging. When she got into her thirties, she started having more chronic health issues. She was making a livable wage but was having a hard time building for the future.

The need for a more flexible schedule, and the ability to make more money led her to set out on her own. She had clients on her first day, including her former company which hired her as a freelancer. A couple of years in, she had a flexible schedule and was making money but she kept saying yes, even when opportunities didn’t align with her values. 

Around this time, Jenni came to me for coaching. Having her own business was much better but she was still writing about concrete. We set out to transition her work from well-paying but low satisfaction to one with more meaning.

She began writing about other topics in order to broaden her brand and to bring her work in more alignment with her values. She also created ChronicBabe, offering support and resources for women with chronic illness. It was a wonderful way to find more meaning and creativity in her work.

She paid the bills with work in the construction industry while blogging for no pay on her passion project. Over time, Jenni began getting asked to consult and to speak at conferences about health issues facing young women.  She felt torn between the work that paid her and what she really loved to do. She wondered if she could make a living working on ChronicBabe. Then her marriage started to fall apart. When the economy tanked again she found herself living alone in an apartment with almost no work, and her symptoms going bonkers. She worried about paying for her health insurance.

Debt was piling up. She was terrified. 

This was one of those moments most solo business owners face, wondering if you should go and get a real full time job. Give up the dream. She deeply considered getting a good old fashioned day job. Instead, she took a bunch of writing gigs that she hated. The situation was frustrating but did the best she could. Though she worked for herself, it was more like a day job.

She kept working on ChronicBabe on the side.

The letters she received from readers were so heartfelt that they moved her to continue working on the site. 

While the day to day hustle was physically and mentally exhausting, Jenni also felt liberated. After a year of steady work with a client that was 80% of her revenue, the organization suddenly had a change in their client load. The work stopped, leaving her scrambling to fill in her pipeline. She decided this was it.

She was never going to hustle like this again.

After that, her side gig became her focus, deciding that everything she did had to be tied to it, only taking work that was related to ChronicBabe. Jenni quit her "day job" 8 years after she started working on her passion project.

Depending on your circumstances, it may not take you this long.

It might take less. It might take longer.

When Jenni first started her side project, she had no plan to drive revenue. She wasn’t trying to make money. She started ChronicBabe because she really believed in it. During the first five years of ChronicBabe, she lost money. When she decided to make it her life’s work, she started to think about how to drive revenue. She began by booking speaking gigs and did consulting.

Over time she created new products like a monthly subscription program which included a series of emails on critical topics, webinars, a huge resource PDF and a private community. Today 50% of her revenue comes from the subscription service, 20% from speaking engagements and 30% from consulting that is related to ChronicBabe. She’s currently at work on an ebook and anticipates that next year the subscription program will be 70% of her revenues.

Jenni's story demonstrates that you can build a meaningful life and business working for yourself. Though she worked for herself, Jenni’s writing in the construction industry was like a day job. Jenni was able to quit her "day job" by:

When to Quit Your Day Job

Be like Jenni, not like my former colleagues. Don't quit your job and then begin building your product. This is the surest way to failure. Businesses take time. Build and nurture those little seedlings now while you have the security of your day job.

The reality is, only you can truly know when the time is right to quit your day job. Here are a few questions you might ask yourself when at day job vs. business crossroads:

- Is your idea clear? Or is it still fuzzy?

- Are you ready to commit to your idea? Or are you still dabbling?

- Are you emotionally, mentally and financially ready to handle the ups and downs?

The answers to these questions will tell you whether it's the right time to quit that day job or whether you need to keep building on the side. But don't be afraid to take your time.

A sustainable business doing meaningful work is worth the wait.



Why Lifestyle Business Isn't a Bad Word

It’s a familiar moment. It’s the moment I tell someone that I work for myself. 

“Do you have a startup?"

No. I am building products though. 

“Is it a consulting company?"

Sort of. 

“Do you have employees?"

Nope. Just me. 

“Oh. It’s a lifestyle business.” 

The last response is done with the side tilt nod, the same one reserved for bad news. A pity nod. That somehow my business isn’t real because it's not cool. They assume I’m a low-cost freelancer beholden to whatever company will pay my meager fee.

I got the pity nod a lot when I lived in a startup town. It pissed me off. It still does.

Working for someone else isn't for me and I don’t want to build a huge business with employees. I wear my independence with pride.

One of the biggest work trends in the past ten years has been the rise of alternative employment, particularly having a business. Having a startup or running a consulting business often confers more perceived prestige. It's as if there's something wrong with having a business that supports your lifestyle rather than consumes it. 

Perhaps because it isn't considered cool, the term lifestyle business became derisive, almost an insult. If other businesses were defined like that of lifestyle, they might be called a vanity, grind, greed or “fairy tale” business.

And, running a startup or a consultancy actually offers little true freedom.

When you have a startup you're beholden to your investors. The pressure to deliver, even when most fail, is sky high. 100 hour weeks with little cash in the bank are pretty much a sure thing with a startup. 

Having a consulting business isn't much better. You have to sell enough business to feed your employees — and manage them too. When a slump inevitably hits those margins can become razor thin. Time away becomes scarce and filled with never ending, last minute emergencies.

When we think of lifestyle businesses, a common image is the geographical and schedule freedom with the ability to work wherever and whenever you want. But geography and schedule are just two of the many benefits that come with having this kind of business.

You can use your best skills rather than trying to become well-rounded. Being an expert allows you to serve your clients exquisitely, letting go of work that doesn’t come naturally. It’s not that you don’t work hard to build your skills. Smart independents actually spend up to a quarter of their time leveling up key expertise.

Freedom from face time. When I worked in offices I hated having to demonstrate to people that I was working. Preening around like a circus act proving your worth is downright demeaning. This is true even for remote work. Perception management occupies a great deal of time when you work for others. You can use that extra time to build a product so you have repeatable income.

There’s also client freedom. You can pick and choose who to work with. Gone are the abusive bosses or no say in the clients you work with. If a client steps over a line or even isn’t a good fit, you can fire them.

Having a lifestyle business gives you financial independence — with more freedom. You're not dependent on a company for a paycheck, beholden to whether they deem you worthy for a raise or a promotion. It’s true that it takes time to get this freedom—especially when you’re starting up as an accidental business owner as a result of a layoff. Once you find your rhythm with the business, the upside is huge. When done right, most independents gain a significant pay increase.  

Finally, working for yourself teaches you how to run a business. It gives you skills you’ll always have — like being able to find and deliver your own work. Being empowered to take care of yourself no matter what, is powerful.

You don't need a startup, even this VC agrees, You’re either venture-backed or a lifestyle business: The big lie.

Wear the lifestyle business badge with pride.