8 reasons why I want to freelance for Toptal (based on my questions for new prospective clients)

In April 2012, I left my previous full-time job as a software developer and started a UX design consulting business. 

And I began this business from an extraordinarily difficult position: no direct experience in UX, no professional network connections who had hired UX designers, no portfolio, and no clients.  I was trying to make a good living in a new line of work.

Like many other new freelancers, I had this key pain point: where can I find work?  My initial projects came from the few network connections I did have.  But if I was going to continue freelancing, I needed to either expand my network or find work online.

At the time, I was going through a steep learning curve in learning how to be a UX consultant.  I joined Elance, oDesk, Guru, and PeoplePerHour and landed no work from any of them.  After wasting inordinate amounts of time responding to proposal requests in a longform RfP style, only to see the work given to unskilled freelancers just because they were cheap, I realized something had to change.

I found that the problem did not lie so much with where I was trying to find work, but with how I was selling my services.  Through Double Your Freelancing and The Businessology Show, I learned how to use UX design as a conduit to provide value for businesses, rather than seeing my UX skills as an end in themselves.

That knowledge prepared me to return to Upwork (previously Elance-oDesk) in late 2015.  I rewrote my profile and became fully booked with just Upwork contracts later that quarter.  Upwork continues to provide a significant source of income for me today as a UX consultant for startup founders - especially technical founders.

On my first call with new potential clients, I like to ask them questions from a list that Jonathan Stark gave me in Double Your Freelancing Academy: “why this?”, “why me?”, and “why now?”.  

So I will lay out the rest of this article in that format, imagining that you are asking me the questions that I usually ask prospective clients.  I will re-order the questions slightly to make more sense for this article.  Here is the original order I learned from Jonathan:

  • Why this?
    • Why do this instead of leaving things the way they are?
    • Why embark on a costly or risky project?
    • What does this project mean for your business?
  • Why me?
    • I realize I’m not your cheapest option.  Why not work with a junior contractor or an offshore team?
    • Why not handle this internally?
  • Why now?
    • Why do you need to tackle this now?  (or: “You’ve known about this for a year and probably would have done something if it’s really damaging the company.  What changed that made this urgent?”)
    • Why not just keep an eye on this (and do some research on your own) for 6 months and decide then?
    • Why have you waited so long to address this issue?

There are 8 questions, so here are 8 reasons why I want to join Toptal's UX Designers group.


What changed in your business that made you realize you should apply for Toptal?

1. Because the consulting landscape has changed, my job is turning into a sales job.

Peter Morville and Louis Rosenfeld wrote one of the most influential books in the history of information architecture (IA) for the web.  They used to run an IA consulting agency called Argus Associates through the dot-com bubble.  However, they closed Argus Associates in 2001 after the dot-com bubble burst.  In Louis’s words:

“We did about [U.S.] $3.5 million in sales in 2000, and were planning for another year of record growth in 2001. But our fourth quarter in 2000 was terrible. In the past, we could discuss a potential $250,000 contract with major corporate customers. Suddenly, large customers were taking their time deciding on a $25,000 project.”

My experience has been similar.  Two years ago, I would land U.S. $30k-50k projects.  Now, $5k-10k - and even as low as $2k - is common.  But I still have to invest close to a day worth of work to close even one of these smaller projects.  

Not to mention, just because I need 5 or 10 times more projects doesn’t mean that there is 5 or 10 times more work available on the market.  It seems like everyone wants to be a remote UX consultant now.  I don’t see enough available work for all of us.

According to Matt Inglot, selling custom work at a low price is a broken freelance business model.  Making the same amount of money as I would from a few larger projects requires selling more of these smaller ones.

How does one land more of these projects?  Talk to more leads.  Quote more projects.

The overhead adds up.  I work more hours to try to make the same amount of money.  And my workweeks turn into client work and sales, which keeps me from investing enough time in advancing my technical skills.  

Who ever became a freelance UX designer because they enjoyed prospecting and sales?  Me neither.  Toptal has more clients who are ready to buy.


Why not leave things the way they are?

2. It’s time for me to get more work with bigger-name clients.

I am an active member of the Double Your Freelancing Slack community, and I completed Double Your Freelancing Academy in 2017.  Whenever I talk with other members of that community or other freelancers on Reddit, I feel like I have to defend my ability to make a living on Upwork.

Why?  Because Upwork has a very negative reputation with most American (and Western) freelancers.  

Upwork does not really stop clients with an average pay of $5 per hour for technical work (less than half of U.S. minimum wage for unskilled work in many jurisdictions) from continuing to find freelancers for commodity work.  While there are good clients on Upwork and I have worked with many, Upwork has a host of other clients who are only interested in the lowest price.

I have landed work with very large companies on Upwork, but I can’t say who those companies were due to NDAs.  If I could share the companies’ names, that may make me never need to look for work again.

I’ve also landed work with a whole slew of great startups on Upwork.  They have good product ideas, hire solid teams, and should do well in their markets.  But again, many of them put my work under NDAs.

Turning a prospective client into a paying client requires trust.  One of the most compelling ways that a freelancer or consultant can do this is to share results they have achieved with names the prospect would recognize.  And practically everyone recognizes many of the big names that have worked with Toptal.


Toptal rejects 97% of their applicants.  Why embark on something this costly or risky?

3. I have confidence that if I get through this application process, the payoff will be solid.

This question doesn’t fit as well as some of the others in this article, but I am including it because I still ask it in my consultations.

There is a risk to me in applying to a platform like Toptal.  One of your sayings is that you reject 97% of all applicants.  But let my clients say it themselves:

“David is a consummate professional and really understands the UX space well. He quickly demonstrated an excellent grasp of a very complex business domain, and even with limited information, was able to deliver an extremely detailed set of high quality UX deliverables. I look forward to continuing our work with him.”
- CEO, technology startup
“David was an outstanding freelancer to work with. He is very well versed in the UX space, but not only on making good designs but understanding the context of who are the users, (and) what are their needs, what are the different tension points in serving different users. On top he was super quick in turning around the work without compromising quality of his recommendations. I will be hiring him again especially for my projects that are more challenging to solve.”
Mid-level manager at a large global company
"I worked with David on a mobile app project for about three months. He impressed me so much with his extensive knowledge of mobile UX, his strong work ethic, and his professionalism that I decided to work with him exclusively on all UX-related projects going forward."
Pietro Rea, Founder, Sweetpea Mobile

The technology startup founder has already hired me for a second project, and that’s just the work we’ve done so far. 

The mid-level manager recommended me to one of her other freelancers (who hired me), saying I was the best UX practitioner she had ever worked with. 

Pietro is an Amazon alumnus whose clients have been acquired by Dick’s Sporting Goods and Spotify, and he’s a published author in several O’Reilly iOS books.

People in significant places are certain that I know what I’m doing.  And I am confident that, if I can work with Toptal clients, my business will take off.


What does this project mean for your business?

4. I can work with bigger-name clients more consistently, which will have a flywheel effect in giving me more work.

I am in two Upwork private talent clouds for companies whose names you would recognize.  But they rarely have UX work available.  One of these two requires UX work to be done onsite, almost 3,000 miles away.

Toptal has a lot of clients whose names I would recognize.  I would expect that since they vet freelancers so strictly, there is also more vetting of clients.  And I have seen several UX consultants - whose names I recognize, and who I respect - get into Toptal without saying anything negative about it.

One of the designers I respect the most is Dan Mall of SuperFriendly.  His redesign for TechCrunch was online for 5 years before TechCrunch recently redesigned their site again.  His agency has worked for names like ESPN, Apple, and Google.  He has published several books in his space and speaks at numerous conferences.  

Yet Dan is barely older than I am.  At some point in his career, he was where I am: having shipped several projects for significant names and trying to build his business.

I want my client work, especially my portfolio and case studies, to reach a point where it sells itself.  Then I can spend more of the rest of my work time building my authority in my niche and constantly improving at my craft so that I can serve my clients better.


I realize I’m not your cheapest option.  Why not work with a junior contractor or an offshore team?

5. Toptal is built around having the most qualified people for the job.

Upwork has a rating system which should work well in theory.  But clients do not always apply even standards.  

One client may give 3 stars for a job that another client would rate at 5 stars.  Some offshore or otherwise low-cost freelancers may rack up 5-star reviews from lenient clients and look like they’re achieving more than a higher-cost freelancer with a 4-star rating from a tougher client.  I had one client there who has never given more than 3 stars to anyone!

It’s like professional boxing.  Some boxers rack up 40-0 or 50-0 records against mediocre opposition, but high-quality wins against opponents who are at their peak establish a fighter’s legacy.  Detractors of Floyd Mayweather, Jr., often accuse him of ducking Manny Pacquiao and other great fighters during their prime years.

In a vetted system like Toptal, everyone is a fighter in his or her prime.  I would not be competing for reputation against a freelancer of a much lower skill level.  

And since I am vetted, I can rest assured that other people on any project team I join are also competent.  I will be able to be more ambitious and creative with my design ideas, knowing that capable developers will be more likely to build them well.


Why not handle this internally?

6. Toptal clients have already decided to hire freelancers rather than staffing up internally.

I’ve told some of my friends that if I were in a business other than UX consulting, I would pick one with a shorter buying cycle.  The biggest lesson that I have learned in prospecting is that most prospects who I contact cold are not at a point in their buying cycle where they can buy any UX services - let alone a $30k or $50k, multi-month project.  Running a UX consulting practice is definitely not like running a retail store, where people walk in, buy an item, leave, and the store owner has made money.

As much as some freelancers hate job boards, most clients on job boards are ready to buy soon.  Toptal’s FAQ says, “In almost all cases, we’ll introduce you to candidates within 24 hours, and 90% of our clients hire the first candidate we introduce.”  This tells me that Toptal clients are serious buyers who will see their projects through to completion.

As a result, here are three things that have happened to me on other sites that I expect would not happen in Toptal:

  • Writing a proposal for a client who decides to not hire anyone.
  • Clients putting my project on hold partway through - without referrals to new clients or compensation.
  • Contacting a prospect only to find out that they do all UX work internally instead of hiring outside help.

Why have you waited so long to address this issue?

7. Toptal was not accepting UX designers yet when I first considered applying.

I first discovered Toptal in 2012 - around the time I discovered Elance, oDesk, Guru, and PeoplePerHour.  At the time, I had little experience in UX, and I expect now that I would not have gotten in.

But also at the time, Toptal was very heavily recruiting developers at the expense of other kinds of freelancers.  So the main reason I did not apply back then was a career decision.  I wanted to build up more experience in UX design and create distance between “David the developer” and “David the UX designer”.  I did not want to be pulled back into development work just to be part of a better freelance community.

In the years that followed, I periodically returned to Toptal’s website.  When you first started letting designers apply, I believe it was still a “UX/UI Designers” option in a site that still heavily emphasized development.  At that time, I was also still happy with where my business was.  I was working on large projects and did not see a need yet to go through Toptal’s application process.

But now, I believe I am a better fit for Toptal.  While most of my portfolio samples are not recent due to NDAs, I have much stronger experience in UX for technical startup founders and development teams and am able to discuss these projects in general terms with you.  I have also graduated from a business academy, published my first UX book, created an innovative UX evaluation service, and started hosting a video series on UX and development.  

I also believe that Toptal is becoming a better fit for me.  Your application process now differentiates between UX designers, UI designers, interaction designers, and user researchers, which tells me that someone there understands UX.  Your client list is also growing to include several companies that I am very interested to work with in the near future.


Why not just keep an eye on this (and do research on your own) for 6 months and decide then?

8. Now is the time to act, not wait.

In short, I’ve already done the research.  Businesses and the people who run them change, and I need to get remote work from a platform that better suits my current and future needs.

In 2012, I was a 26-year-old software developer who was “single with no prospects” and had not found himself professionally.  I spent the rest of my twenties laser-focused on my business, at the expense of almost everything else.

Six years later, I am in a different stage in my life.  I am now 32 years old, engaged to a woman who lives in Australia, and sponsoring her fiancée visa to move to the United States.  Current processing times suggest that the visa will take most of the year; we hope it will be faster.  

But remote work is here to stay for me.  I plan to spend a significant part of the summer working overseas so that I can see her.

On one hand, I am building strong social proof from clients who love working with me.  That is producing a steady stream of inbound leads.  

On the other, I need to do something aggressive in my business or my career so that I withstand changes in the market into married life.  This can mean switching jobs or looking for freelance work in a different place.  The latter option is better for my existing clients who want to keep working with me.  Of the options I have evaluated, Toptal looks the most compelling.


Next steps for you (Toptal)

If what I have said resonates with you and being part of Toptal will lead to paying work for me, I would like to proceed with the next steps for joining Toptal.

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