Interview with Deb, a sales copywriter who transitioned from software development

My background - I am an Indian, with a Computer Science and Engineering background. I started my career 19 years ago in Software Development in a small company, in Kolkata, eastern India. Worked there for a bit more than a year and a half, and then got an opportunity to work in Singapore, where I worked as a developer for 6 months.

My next job was in the UK, where I worked as a developer in a start-up dot-com company for 3.5 years. I didn’t live in London or in a big city. Rather, I worked in a quaint village called Burley-In-Wharfedale (near Leeds, West Yorkshire), that had a population of around 1500 people.

The interesting aspect of this job was that I landed in the UK and the dot-com bust took place. So, just imagine the tumultuous emotions that went through my mind as I grappled with fitting in a completely different culture with no surety whether the company I worked on would still be afloat in a week’s time!

However, I stuck to the grind and we scraped through the initial few months of the cull that was taking place all around the world at that time. During that period, the company I worked for was looking for ways to generate revenue, since advertising revenues were plummeting. So, I suggested that we explore the option of opening a software division of our company to execute IT projects with the help of tie-ups with Software companies in India.

Our directors agreed, and we opened a software division of the company and I was the primary contact person and acted as the business development manager for that division. My responsibilities included liaising between the Indian software companies and the UK principals from whom we procured the IT projects.

I was involved in all sorts of written communication between the parties. Starting from vetting the legal contracts (in conjunction with our companies’ legal team), to co-ordinating the conference calls (This was before the days of Skype, so we used to rely on land lines, which were not very cheap!) between the various parties, and so on.

I came back to India around 14 years ago for family reasons and continued working in business development/IT sales for various Indian companies for 7-8 years. During this time, I travelled to the US for Business trips, specifically Orlando, FL and Boston MA to procure software projects. I also went to Los Angeles, CA, and Las Vegas, NV to attend business conferences.

My last corporate job was back in 2010, wherein I led a team of Inside Sales specialists whose job was to sell a software product to various Fortune 500 companies in the UK and the US. All our selling was over email and the phone.

It was during my tenure here, that I developed a skill of being able to write persuasive emails.

I was laid off in 2015 due to a software paradigm shift and thought of taking this opportunity to reassess where my career was going rather than jump into another job right away. I had heard of remote working/freelancing and was entranced with the idea of working on my own and thought of checking it out.

The next hurdle was deciding which area should I focus on when it came to skill sets. Even though there were a few software sales jobs which were available to be done remotely, at that point in time, they were few and far between.

After much self-analysis, I realized that in most of the companies I worked for, I was given the responsibility of writing sales/marketing collateral, vetting legal contracts, and drafting customer facing emails. Since childhood, my passion was the written word, and I had won a few creative writing competitions during my university days. So, I thought of venturing out there and see if I could find any writing work as a freelancer.

A few web searches led me to the availability of content mills, which paid peanuts. But I thought of applying for a few of them to see if I could make any headway. After a month or two of applying randomly for as many jobs as I could, I got my first content writing job – a 1000 word blog post for a princely sum of $5.

I was happy, yet apprehensive. Plunging into research on the web, I soon came up with reference articles, from where I drafted my blog post. After reading and re-reading it at least four times, I finally submitted the blog post and sat back to wait with bated breath. Less than 24 hours later, the client accepted the article, giving me 5 stars for my work, and immediately commissioned me for 5 other similar pieces.

I was overjoyed, because in the depths of my heart, I’d never actually believed that I’d get paid to write!

Cut to a couple of months later and I was writing my heart out, pouring a lot of time and effort into writing close to 10,000 words in a week. But, soon, I faced burnout and realized that this way of working was not sustainable.

While I was writing for this content mill, I used to read the blogs of established bloggers and freelance writers to get inspiration and some direction on which way to go in my writing career.

During one of these searches, I stumbled upon Upwork and realized that this could potentially be a platform where I could leverage my writing skills to get better paying gigs.

I signed up at Upwork, created a profile, took the skills tests, and started applying for jobs there. It took a lot of struggles, and some time, but finally, I’ve reached a stage now, where I can pay my bills while working full time in a freelance capacity.

Due to client confidentiality and having signed an NDA, I am unable to go into specifics. But at present I am working in the role of a Sales Copywriter.

I weave my words in a way to help my clients get more revenue by persuading their prospects to take action. I specialize in building sales funnels, writing blog posts, persuasive emails, website copy, Facebook ads, and sales landing pages.

My work routine is usually dictated by my clients. The majority of my clients are from the US, the UK, Europe, and Australia. So, time zone differences can be a bit of a challenge at times. If it is an Australian client, then I usually wake up early to attend phone calls and slack/Skype chat sessions. If it is a client from the US, then late nights are the norm.

However, I do try to follow a specific routine to help me get through the day (and night!):

• Wake up around 6 AM and go for a 30 minute morning walk
• Do freehand exercises for 30 minutes
• Check my emails and Slack channels for anything urgent that needs to be actioned.
• Have a look at my schedule (which I write on the earlier night before going to sleep).
• If I have any early morning chats or calls, then I action them.
• Hit the keyboard for a 2-3 hour stretch of writing.
• Break for lunch around 1:00 PM my time
• Write some more from 2:00 PM to 5:00 PM
• Take a break for an hour where I go out of the house to get some fresh air.
• Write some more from 6:30 PM to 9:30 PM
• Break for 30 minutes for dinner.
• Do some light web browsing to catch up for what’s been happening in the world
• Try to hit the bed by 11:00 PM

The above routine is what I follow on an ideal day. However, in the event of client requests for a call or a Skype chat, I obviously must be flexible. There were instances during the early days of my career when I used to go to sleep at 2:00 AM my time to attend client phone calls. However, over the last year or so, I’ve put my foot down and told my clients that I will not be available from midnight my time to 6 AM my time, unless there is a dire emergency.

Most of my clients have been very understanding and have been more than willing to accommodate my request for an alternate time for a phone call.

When I started out freelancing, it took me quite a while to get projects. So, initially, I used to spend a lot of time:

• Doing web research on various aspects of freelancing (the business side, how to market myself, etc.)
• Doing web research on copywriting (how to write persuasively, how to write headlines, how to write sales letters, how to write landing pages, etc.)
• Procrastinating
• Doubting my abilities
• Watching cat videos on youtube

It was easy to slip into self-doubt because I didn’t have a clue how to write proposals for projects. I used to literally spend hours agonising about whether to send out a query letter or a proposal wondering whether I was qualified enough to even bid for a job!

Over time, I realised that it was important not to spend too much time overthinking proposals.

After all, unless you submit a proposal (or send a query letter), how will a prospective client get to know about you?

But at the same time, to actually stand a good change of getting a project, it was important to customize proposals for each job. You really need to stand out from every other freelancer to get shortlisted for an interview call. After that, its up to you to be able to generate confidence in your prospect about your abilities to do the job.

In my view, self-discipline is one of the most important aspects of being a freelancer.

Working on the internet has its own distractions. One minute I’d be doing research on how to write headlines, and the next minute, I’d get a Facebook or Twitter notification. Without thinking consciously, I used to go off-track. And, before I knew it, I’d have spent 45 minutes or more aimlessly browsing Facebook/Twitter.

I found it extremely important to turn off all social media notifications and force myself to read my emails only once every three or four hours (unless there was an emergency email that I had to address). When it comes to emails, it is of critical importance to be prompt in answering clients or prospective clients. So, nowadays, whenever I get an email notification in my phone, I quickly open my inbox, have a glance at the subject line and see who if it is from.

If it is not an important email, I keep it aside to read another time. If it is a client/prospect email, then I either address it immediately, or make a note on my calendar by setting a time (and an alarm) to remind myself to reply to it.

I am a huge fan of Google Calendar when it comes to scheduling client meetings and setting tasks (or important reminders) for myself. I use it not only for my professional life, but for my personal life as well. It has made my life a lot simpler and my productivity levels have really increased because of this wonderful tool.

During my initial days of freelancing I used to set goals for myself the night before a “working day”, and I keep on doing this even now.

I usually write down the top 5 to 6 tasks that I promise to myself to get done within the next 24 hours.

I then dedicate a certain amount of time to each task and make it a point not to get distracted while doing them.

Towards the beginning of my freelance career, I used to spend too much time on the Internet without bothering to work out or take care of my physical (or mental health). Within 6 months of doing this, I realised that I’d put on more than a few pounds and my trousers seemed to have shrunk! I was also not getting enough sleep in a day.

As a result, I was forced to re-think my routine and I made it a point to keep some time aside on each day to do some exercise. Specifically going for walks and doing some freehand exercise in my house. I soon found out that I started feeling a lot more positive and healthy because of this.

Doing some type of physical exercise is, in my view, extremely important in keeping the demons of negativity away.

Another very important part of my routine that I have started doing in the last 6 months is to turn off all electronic gadgets (even my wifi router) and keep them at a reasonable distance away from me before I go to sleep.

Yes, I do, a study desk on one side of my bedroom currently. I do have plans to rent a separate workspace sometime in the medium-term future. The reason is that at times, my bed proves to be too alluring and I find myself taking naps which can be counter-productive at times.

Finding a steady flow of projects is one of the toughest aspects of freelancing. I have faced the typical “feast or famine” cycle that most freelancers go through.

There have been occasions when I’ve not had work for months at a time. Other times there have been occasions when it feels like I am running on a treadmill, just trying to meet the deliverables for multiple clients.

There have been occasions when I haven’t been able to say “No” to a project, simply because my current project was about to come to an end. As a result, the quality of my work suffered, and/or I had to spend sleepless nights trying to complete work – not an ideal situation.

Over a period of time, I have learned from my mistakes, and currently I am in a balanced place. Here is what I try to do when I face either of the above situations:

Having too much work

A very good situation to be in! First, I make an assessment as to my current flow of projects, if I have enough free hours in a day to take on any new project requests. If I don’t, I politely tell my prospective clients that I am booked up for now (I generally tell them when I’ll be available) and to look for somebody else to do their projects. There are a few times, when I refer them to other freelancers. This leads to a win-win situation for everybody – the client is happy because he gets his project done, the other freelancer is happy because he or she gets to do an unexpected project.

At times, this has led to reciprocal referrals by the other freelancer to me!

Not having enough work

Golden rule that I’ve learnt over the last few years – not to panic. During my initial days of freelancing when I didn’t have enough work, I used to plunge myself headlong into applying for projects left, right and, centre.

Just to keep myself busy, I took on projects at rates that were much lower than my usual rate. And more often than not regretted that decision.

I learnt that a lot of low paying clients were usually bottom fishers and would negotiate hard because they could sense desperation in a freelancer. At the same time, they had sky high expectations about the deliverables. What I realized a few days/weeks after taking such a project was that I didn’t have the free time to take up a more lucrative and satisfying project when it came along.

Nowadays, when I don’t have enough work, I do the following:

• Take a break for a few days – go for a short drive out of town for a couple of days in the middle of the week. I thank myself at such times that I am not in a corporate 9 to 5 job, where I have to apply for a holiday a few weeks in advance. The break helps me recharge my batteries and I can get back to my desk reenergised.

• Update my Upwork and social media profiles with updates about the projects I’ve done.

• Start browsing around for projects and apply only for those projects which appear to be a good fit with what I want to do and my rates. Since I have a relatively strong portfolio and decent experience, I start getting interview calls in a short time.

It may take a few days (or a couple of weeks), but more often than not I have my hands full with an interesting project.

The main tools I have used for remote work are:

• Writing - Google Docs or Microsoft Word (depending upon client preference)

• Keeping track of my accounts, invoices and expenses - Microsoft Excel and Google Sheets

• Collaboration – Slack

• Writing specific tools – Grammarly, Hemingway Editor, and Copyscape

• Meetings – Skype, Google Hangouts, Zoom, GoToMeeting

• Project management – Trello, Jira

• Productivity – Google Calendar

• Cloud storage – Google Drive and Dropbox

• Password management – Lastpass and Dashlane

I don’t use the above tools all the time – my choice at times is dictated by client preference. As an example, one of my current clients insists on the use of Jira, Slack, Zoom, Dashlane, and Google Docs. Another of my clients prefers Google Hangouts, Microsoft Word, and Trello.

Here are my top productivity tips and tricks:

• Go for a morning walk and do some freehand exercises at least 5 out of 7 days. Even if I wake up late, I make it a point to stick to this routine as it helps me feel fit and positive about myself, no matter how lousy the previous day was.
• Plan for the week ahead every Sunday night and try to stick to the plan. Even a rough plan helps keep me on track.
• Make it clear to my family and friends that I must not be disturbed when I am working unless it is a dire emergency.
• Turn off all social media notifications on my phone. When I have to meet a deadline, I put my phone in airplane mode.
• Work to music playing in the background. Here are some of my favourite tracks:
  • To motivate myself:
    • Eye of the tiger by Survivor (Rocky III theme song)
    • It's My life - Bon Jovi
    • Don't worry be happy - Bobby McFerrin
    • We are the champions – Queen
    • Fight song - Rachel Platten
  • To focus on my work:
    • Western classical by Bach, Strauss, or Mozart
    • Other instrumental music mainly piano piece
  • To jump out of the bed in the morning:
    • Metallica, Megadeth, AC/DC
  • To de-stress after an intense client session:
    • US Top 40
    • Top of the pops
• Take a nap in the afternoon. Since a typical work week is between 35 to 50 hours (depending upon project pressure), I make it a point to have an afternoon siesta for 45-60 mins. It helps me recharge my batteries during the day and plunge back into work 15 mins after waking up.
• Go for a short walk in the evening. Just before or after the sun sets, I step out of my house and take a stroll in a park nearby. This is different from my morning walks, which are typically high speed and intense. My evening walk is at a slower pace and I do it to relax.
• Try and schedule at least one day in a week to de-stress completely. When I am drowned in work, this typically does not happen, but even if I can’t make it one full day, I make it a point to block at least 5-6 hours of “me” time. I use this time to meet friends/family, catch up on a novel, go watch a movie. Anything to de-stress completely.
• Make it a point to take a 2-day break at least once in 2 months. There are some great guest houses and B&B’s in my city, so for a couple of days I go out with family for a break. I am not able to make it a leisure break all the time, so I either carry my wifi router or ensure that the guest house/B&B has a stable Wifi connection
• Take a 7-10 day vacation once every 5 or 6 months. What’s the point of freelancing if you can’t indulge your passions? Mine is traveling. I make it a point to go for a 7-10 day break at least twice a year. A confession – last week, I took 4 such breaks 😊)

I like a lot of things about remote work, so yes, I have more to add –

• Being able to work in my pyjamas.
• Being my own boss – very important since I know that my own future is directly commensurate with the efforts I put in. All the more important, since I was laid off my last job because of reasons that were not in my control.
• The freedom of being able to work for multiple clients at the same time. I am constantly challenging myself, because each business is unique and whatever I need to do in a new project might be completely different from the previous one. One week I might be writing an email sequence for an e-commerce shop, the next week I might be writing website copy for a small business.
• Having to learn new skills to keep on top of my game – just being a decent writer is worth nothing if you don’t keep yourself updates. I invest heavily in courses to constantly learn new skills – be it free courses offered by [Hubspot], or paid courses on various aspects of content writing and copywriting.
• Being able to take a holiday from work as and when I want to.
• Having the potential to earn much more than what I did as a salaried employee. For the last 6 months, I have consistently pulled in an average monthly income which is 4 times what I used to earn when I was working in my last 9-to-5.
• Last, but not the least – getting a positive feedback from my clients from my clients and the feel-good factor, when they get in touch with me in a couple of months’ time telling me about the positive results they have got by utilizing the copy I wrote.

There are a few downsides about remote work, in my view these are:

• The feast or famine cycle – At times I’ve had more work than I can handle, at other times I’ve had to go weeks before I got a proper project. This can be a challenge at times.
• The absence of face to face interaction with colleagues – One of the biggest drawbacks of remote work is working on my own. Feeling isolated is a reality especially when I am doing a long-term project which means I am tied to my laptop for weeks on end.
• Building fresh client relationships from scratch – Its not just getting a project, executing it and moving on to the next one. Its all about building new client relationships each time you bid for a project so that you can sell your skills to them. If your wavelength and your client’s wavelength doesn’t match, then you could face a problem.
• Clients ending projects abruptly – A couple of times I’ve faced the situation of clients ending projects abruptly. One time, there was this client who’d signed me up for a 6 month plus project asking for a firm commitment from me for 38 hours per week. As a result, I declined a lot of other projects, after starting that one. Imagine my situation after a month when the client told me that he had to end the project even though my work had been exemplary. The reason he gave me was that he was facing a sudden cash crunch because of some another project that he had to work on. Not a very happy situation for me to be in!
• Clients not paying on time or not paying at all – I have been reasonably lucky to have been paid by clients most of the time. However, there have been a couple of instances (outside of Upwork), when the client disappeared without paying me after I did my work and gave it to them. Another instance, I had to follow up with the client for 2 months before I got the payment.
• No company sponsored benefits – As a freelancer, I have to grapple with not having access to any benefits that are usually provided by companies. So, I don’t have any company sponsored medical insurance, pension plan, paid leave, sick leave.
• Juggling multiple clients – I don’t have one boss to answer to which can be an issue sometimes. At times I have more than one client (max I’ve dealt with at the same time is 7 clients). Each client’s work is equally important, and I have to deal with managing their expectations, responding to all of them promptly, and ensuring that they are satisfied with my deliverables. Doing this can be a mental strain.
• Having to take care of all the business aspects myself – Since I am a one-man shop, I have to take care of all the business aspects myself. From marketing, sales, invoicing (when not working on Upwork), troubleshooting technology, keeping track of tax deductible expenses etc.
• No one to back me up if I am injured or sick – A very big problem when working as a remote worker. As an employee of a company, I used to have colleagues who would take up the slack if I was unwell. But, as a remote worker this can be a major issue. I’ve lost one large project because I was out of action for 2 weeks due to sickness.

I do have a few tips to share with aspiring remote workers. These could come in handy for somebody who’s mulling over whether to take the plunge:

• Have at a safety net of 6-9 months of finances in the bank before you take the leap into remote working full time.
• If you have currently have a job, start remote-working gradually by getting your feet wet, one project at a time. It takes time to build your brand, get positive feedback, and build a pipeline of projects/clients. So be careful before jumping all in if you have the option.
• Focus on maintaining a routine. Just because you can work in your pyjamas, doesn’t mean you should. Be disciplined, focus and cut out distractions and procrastination.
• Always vet your clients before taking them on. Before taking on a project, try and do a background check of your potential clients. If you are on a remote-working platform like Upwork, ensure that the client has a “Payment Verified” icon against his name/company name. In my beginning days as a remote-worker, I wrote around 20,000 words of content for a client who was not “Payment Verified”, and he just disappeared after I submitted all my work. If your client is from a source other than a remote working portal like Upwork, make sure you sign a contract with the client and take an advance payment.
• Always have a pipeline of clients. Projects are unlikely to last forever. So, its essential that you keep bidding for new projects. Even if you have a long-term project, you never know whether it will end up being long-term, so be on the lookout for other projects as well.
• Have a work-life balance. Its ever too easy to slip into a 7-day work week for weeks at a stretch. That’s a very bad idea as it can easily lead to burnout. Make it a point to have some off-days during the week.